*****
This is a work of fiction, all characters are 18 or older.
This story involves our main character, who is an actively transitioning TransGirl, her CIS Girlfriend, and a new playmate.
*****
I’d been with Amy for almost two years. When we met, she knew I liked to occasionally dress in female clothes, she said she didn’t really understand why, but in time she became more interested, and actually began to encourage me. She’s a great help, and I’ve learned so much about being a woman from her, and I know this all brought us close., At around the three-month mark for us, I began dressing most of the time while in our apartment.
It felt incredible, and while I wasn’t venturing out, Amy would encourage me to do just that. She started with little things like asking me to answer the door when we’d order pizza delivery, ‘Kim, be a doll and answer the door!’ she’d ask from the bedroom, or if we were expecting a new package (usually something girly for me.) she’d encourage me to answer the door ‘Oh Kim, could you get that, I ordered you a cute dress!’
You get the idea..
I’d begun growing my hair out, and at this point, several more months later, I started seriously considering transitioning. We wear basically living as Girlfriends at this point, and we hadn’t had much sex that felt ‘traditional’ Sure, we fucked, but someone watching would have thought they were seeing two women having sex, aside from the actual fucking.
We arranged all the needed appointments, and I began taking female hormones before we’d celebrated six months together. It took longer than either of us expected, but eventually, I started noticing changes. After the expected emotional challenges, I finally began to notice my breasts growing, my ass started looking juicier, and my skin became much softer.
I was living full-time as a woman, in nearly every way our lives were fantastic, but our sex life suffered, the hormones really impacted my ability to have an erection. This bothered me more than I suppose I expected it to. By this point, it felt almost unnatural to want to penetrate Amy. I felt like that was something I used to do in another life, at the same time, I wanted to continue having orgasms, and continue to be able to give her orgasms through vaginal penetration.
Amy suggested we investigate the possibility for me to have a prostate orgasm, and I happily agreed. We searched for porn that focused on prostate massage, and particularly ‘hands free’ orgasms, the first video we watched showed a Black man slowly moving his large cock into the ass of a cute Blonde crossdresser. He’d pull his dark, glistening cock out of her ass, and it would remain gaped open. It looked deliciously obscene, and Amy had a glazed look in her eyes watching the scene. He easily slipped his cock back into the Blonde and began increasing his tempo, as he did, the Blonde’s smallish flaccid penis flopped back and forth. I don’t know why, but I thought to myself ‘Thank God my dick isn’t THAT small.’ I suppose in an attempt to make myself feel better about the fact that I couldn’t get an erection anymore, at least my dick was bigger than this Blondes.
The fucking on the screen continued, and Amy was rubbing her clit rapidly, her breath coming in gasps, I wanted to join in, but don’t mind admitting, I thought it was hot watching her getting herself off like this, we didn’t typically masturbate in front of each other, we always played together, and I thought it just a bit comical that we were supposed to be watching this to figure out what it would take for me to get off without having an erection, and she was really getting into just watching the scene. The Blonde was on her side now, with her Black Lover pressing the length of his cock into her from behind. He’d gotten ahold of one of her tits, which were non-tits, just a bra filled with something other than flesh, again, I felt somehow ‘better’ than the Blonde, with her little dick, and stuffed bra. She was just a tourist, I was committed. She gasped again, and her soft dick flopped towards her stomach and began spurting semen. She was cumming, and she was cumming a LOT.
Shortly after the Blonde had emptied her balls all over herself, her Lover gripped her hip, and began thrusting into her forcefully, he wasn’t making love to her anymore, now he was fucking her. She understood that he was fucking her now for his own release, and so she encouraged him ‘Come on Baby, fuck me deep, I want your big black cock deep inside me.. Come on Lover, I want you to cum inside me, fill me up..’
He groaned and thrust his cock into her, holding still and the camera zoomed in, you could see his thick meaty block cock pulsing, as he unloaded into her bowels. The Blonde was giddy ‘Ohh, I feel it, ooo it’s soo warm, it feels sooo nice..’ her voice had the tone of someone very proud of themself.
‘That’s some good pussy Baby.’ her Lover said and slipped his softening cock from her ass. As he did, the camera zoomed in once again, and the Blondes’ ass gaped, with a generous amount of cum dribbling out of her hole and down one of her asscheeks.
I had become so transfixed by the scene, that I didn’t realize Amy had rubbed herself to a powerful orgasm, I looked over at her, my mouth opened, and she said ‘Fuck, that was hot, did you see how she came all over herself?’ I nodded, not saying anything. She grinned, and pulled me towards her ‘Eat me, I’m still horny.’ And I slipped between her legs and began lapping at her sopping wet sex.
Saturday arrived, it was still early morning when the doorbell rang. Amy called out ‘Kim, can you answer that please, I’m in the bathroom’ and so I got out of bed, and threw on an oversized t-shirt, and quickly pulled my hair back into a ponytail, and opened the door.
‘Here you go Ma’am.’ the delivery driver offered me two boxes.
I smiled at him, and wondered what we had ordered, then noticed the driver staring at my tits.
To be fair, they were still pretty small, but my nipples had become extremely sensitive, and the t-shirt moving across them had caused umm, well, let’s just say he could see my headlights.
I made a phony coughing sound, and he looked up at me, realizing he was busted.
‘Um, is there anything else?’ I asked.
‘No, No Ma’am, have a nice day…’ he said and headed back to his truck.
I giggled and watched his ass as he moved down the walk, ‘Two can play at that game..’ I chuckled to myself.
I closed the door, and turned as Amy walked into the living room ‘Delivery?’ she asked.
I nodded ‘What did we order now? I didn’t think we were expecting anything?’ I asked.
‘Something I ordered’ she grinned and took the boxes.
‘What gives?’ I asked, raising an eyebrow.
‘You, but later..’ she smirked and then walked off into the bedroom with the boxes, swinging her hips in an exaggerated way.
I followed her into the bedroom ‘Okay, stop playing, what did you get?’
‘Later.’ she grinned.
I shrugged and asked ‘What are we doing today?’
We spent the day doing normal weekend stuff, bought some groceries, had lunch at our favorite Chinese place, did some shopping, bought Amy some clothes, bought me some clothes (well of course!) we got home before dinner, and I started rummaging around in the kitchen, trying to decide what to prepare for dinner.
‘Let’s eat later, are you hungry already?’ Amy asked.
‘I’m not really hungry, I’m, I don’t know I don’t know what to do with myself so I thought I’d make dinner.’ I shrugged.
‘In that case, I have something you can do.’ she grinned, it was that grin that typically communicated that sex would be on the agenda.
‘Oh?’ I raised an eyebrow at her, I hadn’t let the thought of the two mystery boxes slip my mind. ‘What can I do?’ I grinned back at her as she disappeared into the bedroom, and came back with one of the boxes. She walked over to the couch and sat down, patting the cushion next to her, beckoning me to join her.
I sat close to her, and she turned my face to hers and kissed me deeply, pressing her tongue deep inside of my mouth. She lifted her mouth from mine, the look on her face was pure sex ‘First, you start with this..’ and she kissed me once again, biting my lower lip.
I felt her put the box in my lap. I kissed her more, the box could wait. She pushed me away, and laughed ‘Open the box.’ she said.
I pulled it opened, and recognized the contents to be an enema kit, but with some extra bits. Okay, well.. We’d had the hands-free discussion, so this was happening, I already guessed at what the other box must have contained.
‘This makes you fresh back there.’ she said huskily ‘Should I help?’
Naturally, I was excited, at the core of everything the idea that I might be able to cum from anal stimulation was incredible. We’d watched several videos of girls that could cum without their dicks being touched, I really wanted to be able to do this for a couple of reasons, primarily, because it had become nearly impossible for me to cum. My dick wasn’t getting hard enough, and when it did get ‘kind of’ hard, I was stressing so much about it, that I couldn’t get off no matter how hard we tried. The next reason and this was shocking to admit, even to myself, but I wanted to cum ‘like a woman’ specifically, the idea of being able to climax from being penetrated, sounded incredibly naughty to me. The picture in my mind, of Amy kneeling behind me, and pushing a vibrator, or even a dildo into my ass, and causing me to cum left me shaking. I really wanted this to happen.
Amy kissed me again, and asked ‘So, do you have this, or am I helping?’
So, just to be clear, in all the time we’d been together, neither of us ever saw the other use the restroom like that. Sure, we’d needed to go into the bathroom for whatever little stuff if the other had to pee, that wasn’t a big deal, but not the other way, that was private time.
‘Do you want to help?’ I asked, not really sure how I wanted her to answer.
‘Babe, in a little while, I’m going to be up close and personal with that part of you. But you decide..’ she watched me for a reaction.
I stood and reached my hand out for her. ‘Okay then, let’s do this..’
The enema kit was like most others, but this one had 2 extra items. The nozzle included a rubber mid-section that could be inflated/deflated by the bulb that connected to the hose.
‘No accidents this way.’ Amy said, then squeezed the bulb a few times, which caused the rubber part of the nozzle to swell considerably.
My eyes widened at this, and I thought for the first time that all of this might be too much, too quickly.
‘Come on Girl, let’s get you cleaned out.’ Amy said with a wicked grin.
I stripped and watched as Amy adjusted the water in the tub, satisfied the temperature was right, she unscrewed the stopper in the large rubber bag and held it under the rushing water, as she filled the bag, she looked at me and asked ‘Are you as fucking excited about this as I am?’
It’s not like I could have said ‘Actually, I don’t think this is a good idea, let’s go watch some TV,…’ I just nodded, and she shut off the water, lifting the bag and screwing the stopper back in place.
‘Bend over, and spread your legs.’ she instructed, then hung the bag from the shower curtain rod.
I bent over as she’d asked and just decided to go with it, I trusted Amy, and if things started to not feel good, I’d just let her know we needed to stop. She moved closer, and I could feel her hands move to my ass cheeks, squeezing them together, caressing them, spreading them.
‘Okay Baby, are you ready for your douche?’ she purred.
‘mmhmm,’ I nodded. I heard her spit and then felt warmth on my asshole, her fingers were massaging my hole, lubing me with her spit. The nozzle was placed against my hole, and she didn’t say a word, just began pressing it inside of me.
I let out a long breath, the penetration wasn’t nearly as strange, or painful, or.. well, it wasn’t bad. I started to feel like I could just relax and let my Girlfriend give me my first douche, I felt faint tingling in my groin, this felt good. I heard her begin to squeeze the rubber ball, and soon after, began to feel, I suppose the best description was simply ‘pressure’ It didn’t feel like I was stuffed, or about to be ripped in half, I just felt pressure, and then I felt a warmth begin flooding into my bowels.
‘whoah..’ I moved my legs a bit further apart ‘I can feel that.. it’s really warm.’
‘Too warm Hon?’ Amy asked.
‘No, it’s nice.’ I relaxed and let the water continue flowing into me. It felt like it took an hour, but it was just minutes. Now I was feeling more pressure, still not ‘full’ but definitely a pressure, and a considerable need to expel the water.
‘I think I have to go..’ I said, looking back at Amy.
She was grinning, and pointing ‘Look at your Tummy..’
I looked down, and I wasn’t sure, but it looked like my stomach was bulging. I continued to look, and felt Amy step in behind me, she reached around either side of me and softly ran her hands across my stomach.
‘Oh fuck, your swollen, your stomach is as hard as a rock.’ she whispered.
By now, I really needed to sit on the toilet and relieve the pressure inside of me.
‘I gotta go..’ I said, and moved around her, and sat.
‘Not yet Hon, hold it just a bit longer..’ she said ‘Just hold on till you can’t hold it anymore.’
I grimaced and nodded, it felt like I was already at the point, and as soon as I began unclenching a bit, I felt considerably more pressure, and the water inside of me, began pressing against the inflated nozzle. The nozzle was like a balloon, and it was holding the water inside of me. I’d reached the point where I really had to let the water out, and Amy turned a little screw valve, and the bulb deflated, the bulb then shot out of my bottom, and almost the entire bag of water, that had been relocated to my bowels came bursting out with violent force.
Now empty, I sat, breathing hard when the first cramp struck ‘Ooow.. oh shit!’ I groaned.
‘Cramps?’ Amy asked.
I nodded and bent forward once again as another began. She came and stood next to me, pressing my head to her breast ‘It’s okay, they’ll pass.’
After we got me cleaned up, we went into the bedroom and laid down, Amy snuggled next to me, softly rubbing my stomach, and kissing me lightly. ‘Your stomach was soo hard, I think you were really swollen too, God, that was so hot.’ she said. This was a different side of Amy that I hadn’t seen before. It was like she’d become sexually excited, at my discomfort, was this some fetish she had, that we hadn’t talked about? I was pulled back to reality by her voice.
‘Hon? did you hear me?’ she asked and kissed me again.
‘Sorry, I was spaced, what?’
‘Oh, I just wanted to know if you were ready to come like a woman?’ she grinned.
‘Yeah, I’d love to come like a woman..’ I groaned.
She got off of the bed and took a folded towel into the bathroom, I wondered if she wanted me to shower, though we’d already cleaned me up. I heard the water in the sink running as Amy came back into the bedroom. and turned on TV screen, and tossed the keyboard and mouse on the bed.
‘Be right back!’ she said excitedly, and pulled her shorts and top off, swaying off to the bathroom.
I watched her disappear and then stared at the ceiling. We were going to do this, I was excited, I felt naughty for some reason, how strange was that? I was utterly cleansed but felt naughty. I wondered if my stomach really had swelled with the enema.
Amy came back into the bedroom a couple of minutes later with the folded towel, it was clear she hadn’t taken a shower. She set the towel on the bed, and then hopped up, and straddled me, kissing me passionately.
‘This is going to be incredible..’ she hissed ‘I want to watch you come just like a woman..’
‘me too..’ I moaned, the tingling in my groin stronger now, but my dick was just as soft as it had been since we started.
She moved down to my breasts and began sucking, first one nipple, then the other. I felt the tingling in my groin stronger, but my dick didn’t move. She moved past my breasts, and took my soft dick in her mouth, licking, and sucking my balls, the tingling grew stronger still, and yet my dick remained soft. Amy lifted off of me and turned on the monitor, she started up one of the porn scenes we’d watched when the idea of anal stimulation orgasms first started. It was the first scene, with the pale-skinned crossdresser, and her Black Lover.
‘Remember this one?’ she asked, reaching for the towel.
‘Yeah, it’s hot.’ I said, watching her.
Amy unfolded the towel, and inside was a large, black dildo. ‘I’m going to fuck you with this, and you’re going to cum like a woman for me, do you understand?’
I had expected her to have bought something, a vibrator, maybe a dildo, but I didn’t expect this. I didn’t really think I’d be able to take that huge thing inside of me, and I wondered too, was it just a coincidence that the dildo was black? We’d watched plenty of porn throughout our time together, and we’d seen our fair share of interracial scenes, but it wasn’t anything that turned me on more than so many other things, as far as I knew, it was the same with Amy.
I watched her hold the dildo up, and smile at me, then lowered her mouth and pushed the head past her lips.
‘Oh shit..’ I groaned.
She lifted her mouth off the thick head of the dildo and batted her eyes.
‘Hmm? Is everything okay?’ she asked. I nodded and watched as she opened her mouth once again, and pressed more of the dildo past her lips.
My groin continued to tingle, but my dick stayed soft. How the fuck could my dick still be soft watching my girlfriend sucking on that big black dildo? She gagged, and her eyes watered, but Amy’s a Trooper, so she kept trying to force that rubber cock down her throat. To be fair, she managed to get about half of it into her mouth, while I thought she looked incredibly sexy with the dildo in her mouth, I also felt just a bit jealous. We hadn’t played with any sex toys, and I suppose that even if we were involved in a more traditional relationship, one where my dick worked like it used to, I suppose even then, I would have felt a little jealous. But at that moment, I was just enjoying the spectacle of my girlfriend putting on a show for me.
‘Are you ready to get fucked?’ she asked.
I nodded, I was nervous about the size, but I was desperate to get off. I felt like it’d been so long since I came, that when I did, it would be mind-blowing.
‘Lay back’ she said, and she took the towel that she’d had the dildo wrapped in, and lay it across one of our pillows, then looked back at me ‘Ass up.’ she grinned. I lifted my ass off the bed, and she tucked the pillow under me. She lay the dildo on the bed, got up, and went to the closet, returning with the delivery box. She pulled a tube of lube out, and knelt on the bed next to me, and squeezed out a generous portion onto a few of her fingers, and asked me ‘Does my Girl want to cum?’
‘Fuck yes.’ I said, and lay my head back, and tried to concentrate on relaxing my ass. I felt her moving the lube around my hole, and then pressure as she slipped a finger inside. I exhaled and concentrated ‘Relax..’ I said to myself. I felt Amy slip a second finger inside me.
‘How does that feel?’ she asked, as she slowly moved her fingers deeper.
‘It’s okay, are you good?’ I looked at her.
‘Don’t worry about me Silly, you just lay back, relax, and don’t stress, let this happen, I’m really getting excited about making this happen for you.’ she said.
I nodded, and she continued to work her fingers in and out of my ass, I was able to relax further, and while it wasn’t hurting, it wasn’t particularly pleasurable either. It just felt weird, I wouldn’t let myself think that I wouldn’t be able to cum, instead, I started convincing myself it was going to happen.
I felt her fingers withdraw from inside me.
‘Ready Babe?’ she asked.
I nodded.
‘Say it.’ she said, I kept my head back, and opened my eyes, looking at the ceiling.
‘Come on, say it.’ she urged.
‘I’m ready.’ I said, feeling a little self-conscious, how silly was that? my girlfriend had been fucking my ass with a couple of fingers for several minutes, and I was embarrassed to ask her to fuck me with the dildo, silly..
‘You’re ready for what?’ she asked.
‘I’m ready to be fucked.’ I replied.
‘And?’ she pressed me.
‘I’m ready to be fucked, and cum like a woman.’ I said, and it felt good once the words had escaped me. I really wanted this, I needed to embrace it, I needed to move past any embarrassment and own my desire, I didn’t want my own self-conscious nonsense to be the reason I wouldn’t finally get off.
‘I’m ready for you to fuck me with that big cock.’ I said, the words felt so naughty, but they felt good at the same time.
‘You want me to fuck you with this big black cock?’ she teased.
‘God yes, I’m so fucking horny right now.’ I squirmed my ass. pleading for it.
She lubed up the dildo and pressed it against me. ‘Open up for me Sexy..’ she whispered. I tried to let my mind go blank, and accept the Intruder attempting to enter me, I willed my body to relax, and allow myself to welcome the pleasure that would soon be overwhelming me, I felt the head slip past my sphincter, and I involuntarily clenched, letting out a long breath.
‘Oh fuck, that’s big..’ my eyes were wide, I let my eyes move toward Amy, and she was watching me, but her eyes had a bit of a wild look about them.
‘Still okay?’ she asked.
I nodded. and took a few deep breaths.
‘This looks incredible, the head is inside you right now. Fuck this looks sexy.’ she moaned.
She applied more pressure, and I felt a bit more slip inside me, it felt like someone had a hand up my ass, and I concentrated on remaining as relaxed back there as I could. She pulled back a bit, and then pressed forward once again. This back and forth kept up for what seemed like an hour, but it had only been minutes. My body began adjusting to the dildo, and Amy began to more easily penetrate me, pulling more of the dildo out before sinking it back in, my ass allowing more to be swallowed up.
This felt different than her fingers, it was obvious it was a toy and not a person. I felt filled, well, more than filled. The sensation I had was that I wanted to bear down and squeeze the dildo from inside me, but I knew that if I did that if I didn’t allow myself to be taken like this, and for the stimulation to build, I wouldn’t orgasm, and that was the point to all of this.
I focused, as Amy continued fucking me with the dildo.
I closed my eyes and imagined what it must look like, my poor virginal ass being stretched open as the thick black dildo moved deeper still. I liked the thought of that. Of being stretched open. it would certainly be looser if I could cum. I let my head roll from side to side as I began to feel waves of pleasure begin to build deep within me.
I felt the dildo stop moving, and heard Amy say ‘Don’t move Hon, hold still.’ I focused my eyes, and looked at her, and saw she was aiming her phone, preparing to take a photo of the dildo in my ass.
‘How does it look?’ I asked.
She looked at me and said ‘I wish you could see this, I really wish you could see what this looks like.’
I smiled lazily at her and asked ‘Fuck me some more? It starting to feel nice.’
She nodded and began fucking me with the dildo once again. I closed my eyes, and let the sensations wash over me. I thought of the Blonde in that first scene we’d watched those days ago, while her Lover slid his cock into her ass, while he made love to her.
‘I want to be on my side like that woman was..’ I whispered.
I began changing position, and Amy kept the dildo inside of me, repeatedly telling me how sexy I looked taking that big black cock. On my side now, propped my upper leg up, with my feet resting on the mattress. Amy resumed fucking me, and reached between my legs, and held my penis, my soft penis was flopping around, just like the Blondes had been. I looked down and watched it flop around, it looked smaller than it had been. It looked as small as the Blondes had been. I reached past my shrunken testicles, and my fingers bumped into the dildo. I spread my fingers on either side of it and felt it sliding in and out of me. I could picture what it all must have looked like. I understood the Blonde’s pleasure, I was being opened, stretched, used, in the same way she had been. I focused my attention on the pleasure centered deep inside of me and waited for the inevitable climax to overtake me. It was going to happen, I felt so happy, to be clear, I also felt like a slut, but I had fully relaxed, my ass had opened and the dildo was creating wonderful pleasure in a part of my body that I wouldn’t have imagined possible. The sensations increased, and I surrendered, waiting for my own soft penis to spurt cum all over myself as the Blonde had done, it felt wonderful, it felt intoxicating, just a bit more and I’d be there, just a bit more..
Except, that bit more wouldn’t happen. I was so close, so slutty, beyond what the Blonde had felt, surely. I was on the verge, but that tiny bit more needed, just wouldn’t come.
Ultimately, we stopped, and while I told Amy how incredible it felt, and thanked her for how she had given me such incredible pleasure. The experience depressed me quite a lot. I was soo close, I could feel how close I was, and while it tore at me, I decided that ‘next time, it’ll happen.’
But it didn’t happen, we tried for a month, we tried a lot, and each time, I’d get so close, I’d be right on the verge.. but each time, it wouldn’t happen.
It took a bit, but eventually, Amy realized I was pretending things were okay. We still had an active sex life, and I’d happily lick her to orgasm on a nearly nightly basis, but I felt more and more like I was giving up too much. I loved that my breasts were growing and that they were so sensitive. I loved how my body looked in a mini dress, how shapely my ass and legs looked. I knew that the longer I stayed on hormones, the more feminine I’d look and think, but looking how I wanted to look, didn’t seem like it was enough. I wanted to have an orgasm, I felt like ‘even that crossdresser could get off through anal, I’m full of hormones, it should be so much easier for me to orgasm from anal!’
It didn’t seem fair, and I know my relationship with Amy began to suffer.
One night after we had fooled around, Amy asked if I wanted her to bring ‘our friend’ into bed. The dildo had become known as ‘our friend’, I wanted to try again, but had found it more difficult to get into the kind of mental space that would allow me to experience the kind of pleasure that I’d originally felt when we first started playing with ‘our friend’. She could see it was affecting me ‘If you want, I could suck it again, you seemed to like that.’ she said, snuggling against me.
She had a point, it was extremely exciting to watch her play with the dildo herself. Now, it’s important to note, I didn’t have any desire to watch Amy fuck another guy. I didn’t have any interracial fetish, and I wasn’t secretly hoping she’d go find a Black Stud to fuck her brains out and make me watch. If other folks are into that, good for them, this just wasn’t something either of us was interested in.
So watching her suck the dildo wasn’t something I used as a safe solution to wanting her to find a new Lover. She just looked so sexy playing with it, I imagined myself being able to get an erection, and pictured her doing all those things to me.
‘Do you like watching me suck this big dildo Baby?’ she purred. Fuck, she’s so sexy.
‘Uh huh’ I watched her performing her Porn Actress routine, I softly moved my hand on my dick, hoping..
She’d been licking and sucking the dildo for several minutes, and I was breathing hard, she’d had me so aroused watching her perform.
‘I’m really horny Baby.’ she purred, and slowly dragged her tongue in circles around the dildo’s head. Her eyes watched me, which only excited me further. She kissed the head of the dildo, before sliding it past her lips into her mouth, and bobbing up and down, making gagging noises as she did.
I imagined that dildo was my own dick. I pictured her sucking me, the way she was sucking the dildo.
‘You like?’ she asked between licks.
‘Oh yeah, I definitely like.’ I responded, watching her perform.
She grinned at me, then laid back towards the end of the bed, letting the dildo move past her lips once again, she spread her legs and began rubbing her clit with her free hand.
‘Fuck, that’s sexy..’ I groaned. One hand softly moved up and down the length of my soft penis, the other held to one of my breasts, pinching a nipple between thumb and forefinger..
She pulled the dildo from her mouth and grinned at me ‘You’re looking pretty sexy yourself Babe. She brought the hand she’d been rubbing her clit with to her mouth, and licked her fingers, savoring the taste of her juices, then slipped her hand back to her pussy and spread her lips. My eyes were laser-focused on her sex, I pinched my nipple a bit harder.
She lifted the dildo once again, but brought the head to her spread pussy lips, and began rubbing it up and down, watching me.
I groaned loudly. She hadn’t done this before, she’d only sucked the dildo. I looked up from her pussy to her eyes and saw hers locked on mine, then they rolled back into her head. I looked down once again and realized she had pushed the dildo into her soaking wet pussy. She held it still and closed her eyes, and then slowly began moving it in and out.
The sight of my girlfriend’s pussy filled with dildo, no, filled with that big black cock was mesmerizing. She gasped and whispered ‘Fuck, this is big.. really big.’
My eyes would move from the scene playing out in her pussy, to her face, each sight incredibly sexy. I had both hands on my tits now, rolling my stiff nipples between my fingers and enjoying the little electrical jolts of pleasure they were causing.
She began thrusting the dildo deep into her pussy, it reminded me of the way the Black guy had begun fucking the crossdresser after the crossdresser had cum. That big dildo getting hammered into my girlfriend, as she moaned ‘fuuck that’s good.. oh fuck.. oh FUUCK! OH FUUUCCK!’
I watched as Amy came on the dildo, her legs shaking erratically, with her eyes tightly shut. It was one of the most erotic things I’d ever seen. I don’t know why, but at that moment, I wanted that dildo in my ass, hammering away at me, the same way it’d been hammering at Amy’s pussy a minute before.
‘You’re not mad… are you? ‘ she quietly asked.
‘Huh? no, NO, that was wild, that looked soo good..’ I replied, wide-eyed.
‘I love you, and you know, that it’s just a toy, I’d never do that with someone, I’d never cheat..’ she said.
‘I know, it’s okay, that was just really hot, I’ve never seen you do anything like that before..’ I said.
She watched me silently for a few minutes, then said ‘I’ve thought about you.. with someone else.’
‘I heard her words, but didnt understand ‘someone else, as in no longer with you?’ my heart was pounding in my chest.
‘No Silly, I will always love you. I meant I’ve thought of you.. playing, with someone else.’ she said, her voice seeming unsteady.
‘Amy, I love YOU, I don’t want anyone else.’ I smiled at her.
‘I know you love me, I just remember you saying the dildo got you so close to cumming’ she stopped, then looked away. ‘I just thought, I mean, if you wanted to, if you wanted to try..’
I watched her, listening ‘…wanted to try?’ I asked.
‘If you wanted to try, you know, the real thing..’ she said, looking back at me.
‘You mean, you want a guy to fuck me?’ I asked her, pretty sure I knew that was exactly what she was thinking.
‘Yeah, if you wanted to, I wouldn’t be mad. I know it’s been a long time for you, and I know you’ve gotta be going crazy by now.. and.. ‘ she stopped, waiting.
Would that be what I needed? The dildo always got me close, but never close enough. Was that because I may have still had some hangups? I didn’t think so, I had really hoped the dildo would have solved the problem, that would have been the easiest solution. Would a real cock be what I needed? I didn’t really have any great desire to have some guy fuck me.. I liked women, not guys.. I just happened to enjoy being a woman more than being a guy, I guess that made me a Lesbian, okay, that’s fine, but back to this idea of actually getting fucked.
‘What do you think? Do you think that would fix me?’ I asked.
‘Babe, you don’t need to be ‘fixed’ we both know your meds are causing this. Let’s do this. How about we get you laid, and then if that doesn’t work, we’ll talk about next steps.’ she said, attempting to stay logical, but she just suggested that a guy fuck me.
I listened to her, thinking about it, wondering if that would be what I needed. Hell, what if it was? What if the final bit that I needed to finally cum, was a real dick in my ass. Then what?
‘So let’s say we explore this.’ I said ‘where would w go from here, I don’t know any guys lined up waiting for someone like me to…’ I shrugged.
‘We get you signed up on a few websites.. We take a couple of sexy pictures of you, we’ve definitely got to include the photos I took of you the first time we played with our friend…’ she said.
‘That simple huh?’ I asked ‘We’ve definitely got to set some expectations, I mean, there’s gotta be some requirements that need to get sorted out..’
Amy thought for a moment, then grinned, and said ‘Just two things, as far as I’m concerned.’
She picked up the dildo, and gave it a lick ‘He needs to be hung.’
I nodded, watching as her tongue worked on the dildo.
She stopped, smiled, and moved the dildo to my lips, then finished with ‘and I want him to be Black.’
I opened my mouth, and she pressed the dildo past my lips. She tilted her head, and I wondered what she was thinking. ‘A Black guy.. a hung Black guy..’ I closed my eyes and imagined his cock in my mouth, and began sucking.
We were both surprised at the number of messages that had flooded my inbox. We’d posted an ad, with the same profile pictures, the same outfits, and the same photo of my ass stretched tightly around the dildo. The profile made it clear what I I was looking for.
‘Wanted:
This dirty TransGirl is looking for a fit, confident, and hung Black man to push me over the edge, and enter the world of prostate-induced orgasms. You should be at least 30 years old, have good hygiene, and be in reasonably good shape. I’m real, you need to be as well.’
While the profile was clear, the large majority of messages were from old fat older White guys, some were clearly in their 60’s, there were several from Black guys that immediately made demands as if I were some dumb slut that was looking for a very different kind of relationship. But there was a handful that looked promising. I sent a message back to one of the guys that had an interesting profile.
‘Why do we make feeling so good so difficult? You may have put up some fences that I may be able to help you take down. Interested?’
His profile included several photos of him playing basketball, I could see he was in shape, clean-shaven, he was probably in his early to mid-thirties. The last photo showed him standing naked in front of a bathroom mirror, holding his phone up. His cock was semi-hard, and we supposed it to be around seven inches in that state. Amy thought this was the best profile so far, and I sent him a quick reply.
‘Thanks for checking out my profile, and possibly being interested in getting together.
Call me, xxx-xxx-xxxx
Kim’
I hit send and shivered, holy shit, I was trying to actually hook up with a guy. Why was that so, I don’t know the best way to describe it, but it felt, forbidden.. As if I had opened a door that couldn’t be closed.
About thirty minutes later, my phone rang.
‘Hello?’ I answered nervously, the calling number was unknown to me.
‘Hello, Is this Kim?’ the man on the other side of the call asked.
‘It is, who is this?’ I knew it was him, I breathed, and concentrated on staying calm, and not making a fool of myself.
‘It’s Ray, you sent me your number, a little while ago, is now a good time to talk? he asked.
‘Hi Ray, sure, now is fine. How are you?’ I tried to make small talk.
‘I’m better now.’ he laughed ‘You wouldn’t believe how many phony responses, wrong numbers, phony people, you can imagine.’
‘Actually Ray, I’ve never posted a profile on one of those sites before. I’m with someone who I love very much, and she means the world to me. It’s just that, it’s been a while since I.. So I don’t know how familiar you are, but when you take female hormones..’
‘It’s okay..’ he said.
I paused.
‘I understand, it messes with things, it helps you be who you want to be, but it makes it difficult for you to hold on to parts of who you were.’ he summed it up and made it sound like this happened to everyone in a situation similar to me.
‘Okay, so what I was really interested in, well, we’ve played, my Girlfriend and I, we’ve used a sex toy, and she’s been able to use it, and get me really close, right on the edge, but not quite over it.’ I sighed ‘So we thought, maybe if I met with a guy, and the chemistry was good…’ I paused.
‘When would you like to meet for a coffee?’ he asked.
This all happened faster than I had planned for, I looked at Amy, but she just looked back, letting me decide what to do next.
‘Is tomorrow night too soon?’ I asked.
‘Tomorrow night is fine, do you know Common Grounds near the Parkway Mall’ he asked.
‘Yes, I know the place.’ I answered. What was happening here? Was I actually doing this?
‘Does 7:00 pm work for you Kim?’ he asked.
‘Sure, 7 is fine.’ I was on auto-pilot.
‘Kim, it was great chatting with you, and I’m really looking forward to meeting you tomorrow, don’t feel any pressure okay? We’re just going to talk and get to know a bit about each other. Have a nice night.’ he said, and I had somehow already known I would be bringing him home with me.
Amy waited till I set the phone done. ‘That sounded like it went well.’ she smiled.
I blinked a few times ‘It felt, a little bit like I was outside of my body, just listening to someone else talking to him.
‘Are you excited?’ she asked.
I nodded ‘Yeah, nervous mostly.’ I sighed, that self-doubt had begun to creep in again.
‘Well, I’m mostly excited.’ Amy said, and stood up, reaching her hand out to me.
I took her hand and stood ‘What? What are we doing?’ I asked.
She pulled me into a hug, and we kissed, our tongues playing together. I felt her hands slide down to my ass cheeks, and she squeezed softly. She lifted her mouth from mine, and giggled ‘I’m so jealous of your ass.. he’s going to love it.’ I blushed and considered her words. If I wanted it to happen, the following evening, I could find myself with a guy, I could end up getting fucked by a man, if I decided I wanted to, I could have a man’s cock in my ass, his cock may even make me cum. This could all happen the following day. It was a lot to consider.
‘Are you okay? Amy asked, with a concerned look.
‘Yeah, I’m good, I’m just, there’s a lot going on up here..’ I pointed to my head.
‘I have the cure for that..’ she giggled ‘let’s go shopping!’ and clapped her hands.
She wasn’t wrong, shopping usually helps everything.
We drove to Parkway Mall, and passed Common Grounds as we neared ‘Thats where I’m meeting him tomorrow.’ I said pointing.
‘Meeting who? Amy played dumb.
‘You know who I’m talking about. don’t play.’ I said.
‘No, tell me, who are you meeting there tomorrow,’ she pressed on.
‘Ray, I’m having coffee with Ray there tomorrow.’ I replied, saying that, sent a shiver through me.
‘Who’s Ray? she was committed now.
‘A guy I met online, he wants to meet up..’ I decided to play as well.
‘You met him online? You mean, on one of those hookup sites?’ she asked.
I nodded ‘Yeah, his profile looked pretty hot so..’
‘What does he look like?’ she asked, smiling.
‘He’s sexy, he looks fit, he’s a bit older than me, but whatever..’ I shrugged.
Amy grinned ‘Older, maybe means more experience..’
‘Maybe, so yeah, tomorrow we’re going to have coffee there.’ I looked back out of the car’s window.
‘If you like him, will you see him again?’ Amy pressed further.
I nodded ‘Yeah if he’s as sexy tomorrow when we meet as his pictures look, I think I’m going to bring him back home with me.’
Amy gasped ‘Oh my God, really? if you bring him home, what would you do?’
I could tell she was aroused, her breathing easily gave her away, but so was I, and I was enjoying this.
‘If I bring him home, I’d make out with him. I’d let him stick his tongue down my throat..’ I said. ‘I’d let him hold me close, and squeeze my asscheeks.’ my nipples were stiff and pressing against my bra. ‘I’d let him fondle my tits, let him suck on them. bite on them.’
Amy didn’t say anything, we pulled into the Mall parking lot and she found a space quite a distance from one of the entrances.
She turned off the car.
‘I’d pull his zipper down, and reach into his pants..’ I grinned wickedly at her, she had started this game, and I intended to finish it. ‘I’d feel the heat from his cock and wrap my fingers around it while he sucked on my nipples.’
Amy’s chest was heaving. she remained silent, and I reached my hand over and pulled at the hem of her skirt, she lifted her ass, and raised her skirt up to her hips., I moved my hand to her panties and began softly rubbing.
‘As I stroke him, his cock would begin to grow, and I’d realize how big he is.’ I teased. ‘ So I’d unbuckle his belt, and pull his pants and boxers down, so he’d feel more comfortable as he sucked my tits.’ Amy moaned as I continued to rub her pussy through her cotton panties.
‘I’d look down, and see his cock jutting out from his groin as my hand slides up and down its length.’ my voice was lower now, my own excitement causing me to tremble. I continued rubbing Amy’s pussy, her panties were now a soaking wet mess, and her hips jerking upward told me she was close.
‘His cock is so big, I’d take his face in my hands, and bring his mouth to my own, and offer him my tongue.’ I whispered ‘He’d suck my tongue into his mouth, and I’d let myself go, I’d move my mouth from his, and then while looking directly into his eyes, sink down onto my knees.’
Amy was going to cum at any moment, but she had started all of this, and so now, we played by my rules. I slowed my hand on her pussy, and she made a little whining noise.
‘I’d continue to stroke his cock, so close now I could smell his scent, my eyes wouldn’t leave his, he’d just watch me stroking him, fully erect and large enough that my hand couldn’t close around him..’ I continued to tease her, but my nipples were sending electrical jolts through my body, and I wished Amy would tear my hand away from her pussy and suck each of my tits, squeeze them, to do whatever she wanted, I was desperate for release.
‘Fuck, dont stop..’ she finally said.
‘You want me to keep telling you how my date with Ray is going to happen tomorrow night?’ I purred to her.
Amy’s eyes stayed closed, with her head rested against the back of the car seat, to anyone walking by, it looked almost like she was just taking a nap.
‘I’d lick my lips..’ Amy squirmed, working to get more of her pussy against my hand.
‘I’d bat my eyelashes at him, and ask “Would it be okay…” Amy was grinding against my hand.
‘would it be okay… if I sucked.. your big…. black… cock?’ and then closed my lips around his thickness.’ I whispered, my breath a ragged mess.
Amy had grabbed my hand and was humping against it, she cried out as I rubbed her pussy while she came, and collapsed back into the seat of the car. Breathing as she had just run a marathon.
She opened her eyes and looked over at me, and shook her head ‘Kim, you are such a dirty slut, I hope tomorrow night goes just as you described.’ she lifted her ass off of the car seat again and slid her soaked panties down her legs.
‘Let’s shop..’ she said.
The next day was impossible, we both worked and didn’t get back to the house till almost 5:30. I was excited, nervous for sure, but at this point, very excited, and so I hopped into the shower and did all the girly things I had to do. Amy and I had picked out a sexy outfit from the previous nights shopping, a beige mini-dress, with a darker wide belt, I wore my Victorias Secret bombshell bra, which made my tits actually look big, not just ‘getting there..’ nude thigh-highs, a black thong and black peep-toe sandals with a 4″ heel.
After a close inspection by Amy, my makeup was approved, and she picked out her favorite perfume, ‘Black Opium’ from Yves Saint Laurent.
‘So, what if he wants to come back here? I mean, if things go well.’ I asked.
‘You definitely need to bring him back here if things go well’ Amy said.
‘It’s just, I know why we’re doing this, and I don’t know if, look, if things start getting heated, I don’t want you to feel…’ I hesitated.
‘Jealous?’ Amy asked.
I nodded ‘I’d rather just not do this at all if it would cause you to feel bad, or hurt, or jealous, I just don’t want..’
‘It won’t, I know why you are doing this, I know why WE are doing this, it’s not fair that you haven’t been able to get off, for months now, I’d be out of my mind. This isn’t a case of you running off to be with someone else because you just want to play. This is you, hopefully, getting what you need, to feel like a human being.’
I looked at her, silently.
‘It’s okay if things go well, and you bring him back here, I can stay in the living room, and you two can go play in the bedroom.’ she said, nodding reassurance.
I didn’t have words.
‘You’re going to be late, now get that sexy ass of yours moving.. call me when you get there..’ she said, then turned me around. I grabbed my purse and keys and closed the door behind me.
‘Amy, I made it, I’m parked outside, I can easily start the car and come back home right now..’ I said.
‘The only way you’re coming back home is if you bring your date here with you, have fun..’ and she hung up the phone.
‘Hi, Ray? I smiled as I walked to his table. He stood up, smiled and opened his arms
‘Kim, wow, you look amazing..’ we embraced, and I could feel how solid he was. Ray didn’t appear to be one of those cut-up model types. He looked solid, not flabby, he wasn’t covered in muscles, but I could tell he was powerful. He kissed me on the cheek, and we sat.
A girl walked over to our table and asked what I’d like to drink, and disappeared back behind the counter. I looked back at Ray and said ‘Can I be honest?’
He nodded ‘Of course..’
‘I’m nervous about all of this, excited, but nervous..’ I confessed.
The girl returned with my coffee, then disappeared behind the counter somewhere.
‘Why are you nervous?’ he asked, his eyes darker than I’d imagined, in fact, he was darker than I had imagined.
‘It’s the first time I’ve used one of those sites, first time, you know..’ I shrugged.
‘You mentioned you have a girlfriend.’ he said ‘Is she okay with us meeting? She’s not, jealous?’
‘No, this is kind of actually both of our idea.’ I grinned a bit, ‘well, some of it was my idea, and some other details were her idea.’
We chatted for about 45 minutes, and I found Ray to be intelligent, charming, and respectful. He also made it abundantly clear, in as gentlemanly terms as he could, that he wanted to get to know me better.
‘Hi, Amy? Yep, everything is fine. I know, I know, I should have listened to you.. anyway, listen, we’re coming home. Yeah, yep, I’m here with him now. haha, okay, Ray, Amy says ‘Hi’.. okay Baby, talk soon.’ and I hung up the phone.
Ray stood, and extended his hand ‘Well Beautiful, it sounded like your girlfriend is okay..’
I nodded and took his hand as I stood and he wrapped his arm around my waist as we walked out of the coffee shop. As we left, a middle-aged couple walked across the parking lot saw us standing there. The guy gave a look, and his face twisted a bit, clearly not approving of the ‘couple’ that we appeared to be.
Without thinking about it, I turned into Ray and said ‘Alright Lover, let’s go home.’ and leaned in, he pulled me closer, and pressed his lips against mine.
Holy shit, a guy was kissing me.
His mouth opened and I felt his tongue push forward, his hands had found my ass, and he pulled me closer still. I could feel his cock stiffening, and pressing against me.
He was kissing me, and he wanted to fuck me..
As these thoughts raced through my mind, I didn’t think to question why my entire body was tingling, why my nipples felt like the epicenter of my universe, I just felt an animal desire to open my legs and surrender to this man.
From a single kiss.
I heard the door close as the couple passed and entered the coffee shop, I leaned back, convinced we had made a scene, and semi-apologized ‘I just saw the way he looked at us, and it pissed me off, so I just..’
‘Wanted to piss him off too?’ Ray finished for me.
I nodded ‘I mean, I wanted to do that anyway.’ I grinned at him.
‘That was perfect, you pissed off a racist, and in the bargain, I kissed the most beautiful woman I’ve seen in a very, very long time.’ his smile would have disarmed anyone, his perfect white teeth such a contrast to his rich dark skin.
We walked to our parked cars holding hands along the way. ‘I’m just about 5 minutes from here, follow me, okay?’ I asked.
He grinned, moving his head to look at my ass ‘Happily, especially with that view.’ that smile popped again, God, I wanted to fuck him right there in the parking lot.
I wiggled my ass a little for him ‘See anything you like?’ I teased, and he had me in his arms once again, our kiss had become more passionate this time, and I relaxed, and let him hold me.
He raised a hand and cupped one of my breasts, then broke our kiss and looked at me. His hand began to softly squeeze, my nipple now easily visible, his fingers drawing an outline around it ‘I can’t wait to suck your tits, Kim..’ his voice had changed, it was thicker, filled with desire.
‘Follow me..’ I said softly and got into my car.
As we drove, I’d regularly check the rearview mirror to make sure Ray was still right behind me. There were no longer any nerves about what I had hoped would happen, or if it would be awkward, I just wanted to get him home and let him consume me.
‘Amy, we’re heading back to the house now, yeah just a few minutes away. Yeah, we kissed, it was incredible, I’m sorry, that seems cruel to say, no.. but we didn’t talk about that, I just don’t want you, no, I understand, look, I’m going to fuck him, he’s really into me, I’ll just introduce you and will leave you alone, and go off into the bedroom. Okay, I love you too, I really love you, Amy.. okay bye.’
I hung up the phone. and parked. My heart was pounding in my chest.
‘Amy, this is Ray, Ray, this is my Girlfriend Amy’ I said, introducing the two. ‘It’s a pleasure to meet you, Amy, Kim here is a very lucky woman.’ he said as his eyes roamed across my Amy.
‘It’s nice to meet you too Ray.’ she smiled at him, then similarly gave him the once over. ‘Well, don’t mind me, I’m just watching TV here, you two go enjoy yourselves, she looked at me and winked.
I led Ray to the bedroom, the room I had shared with Amy, our bedroom, our bed. It felt wrong to bring him here, but it also felt good, in a bit of a wicked way. All of this wasn’t entirely my idea, Amy had seemed just as turned on as it all as I had. As Ray entered the bedroom, I closed the door behind him, well, I mostly closed it, just in case Amy wanted to sneak a peek at whatever we might be doing inside.
He turned me around and began kissing me once again, and I willingly opened my mouth as he explored my depths. I pressed myself against him, and moved my hands to his arms, squeezing, he felt as if he had been chiseled out of stone. He kissed me once again, and then softly placed his hands on my shoulders, breaking the kiss and looking into my eyes. He said nothing but pushed down on my shoulders, just slightly. I understood immediately what he wanted.
His pants were around his ankles, and my mouth was filled with his dark cock before I realized it. He was big, as big as ‘our friend’ and maybe a bit larger. I could only manage to fit, possibly half of him in my mouth, but could tell from the noises he was making, that he approved of my efforts. I moved my mouth from his cock, and began licking his length, leaving his glistening black cock sticking out proudly from his loins.
‘This is for me.’ I thought. I wanted to please him desperately, I wanted this experience to be incredible, I wanted to show him how badly I desired him.
‘Baby, your mouth feels real nice..’ he said, reaching his hands down to me, and bringing me back to my feet. He held one of my hands over my head and spun me around, whistling lowly. ‘I’m gonna eat you up Girl..’ his voice nearly sounded like a growl. He turned me around, and unzipped my dress, sliding it down my body, and turning me back to face him. His eyes rested on my tits, and I reached behind, unclasping my bra and tossing it onto the dresser, I looked back at him and the lust was obvious in his gaze.
‘Damned Girl, those titties look just as fine as that sweet ass.’ his hands pressed into the flesh of my breasts, and he whistled again, ‘Nice, soft natural titties.’ he said and pressed his mouth to one of my nipples, sucking noisily. This was very different than sex with Amy, we were soft, gentle, slow (mostly) when we played, but Ray was making a feast of my tits, it made me feel like I was just there to make him feel better, I was there just for his enjoyment, and that excited me even more.
‘WHACK!’ I felt a stinging pain on one of my ass cheeks, and realized he’d slapped me, I gasped. My ass was burning, but that was fine. Ray was establishing dominance, and I liked it. He rubbed my asscheeks and said ‘Baby, it looks like you stole this ass off a Black Girl.’ and covered my mouth with his once again. I welcomed his tongue back into my mouth. It felt natural, the more he played with me, the more I wanted him. I closed my eyes, and let my tongue twirl against his. I reached down and took his hard cock in my hand, and gently stroked him while his tongue moved inside my mouth. I dreamily opened my eyes and could see Amy standing in the open doorway, she was squeezing one of her nipples through her shirt, and had her other hand inside the waistband of her skirt. I closed my eyes once again, and slowly stroked him. My Girlfriend watched quietly, but not so sneakily in the doorway.
Ray moved his hands to my face, gently cupping my cheeks, and broke our kiss.
‘Let’s get more comfortable Baby.’ he said with a grin. He picked me up effortlessly, and set me down on the bed, moving on top of me. He slipped an arm under one of my thighs, and leaned forward, moving to kiss me again, but only briefly.
‘Your Girlfriend is watching us.’ he whispered.
I looked into his eyes, grinned wickedly, and whispered back ‘I know.’
He nodded, and simply asked ‘Are you ready for this big dick Girl?’
I moved my mouth to his, sucking his lower lip into my mouth. He correctly assumed I was in fact ready. I felt something hot, and hard moving between my spread ass cheeks. Amy moaned in the doorway, watching as her Girlfriend was about to be fucked, in a sense, for the very first time.
Ray spit into his hand and began lubing his cock. ‘I can’t wait to get inside you Girl, but I’ll go slow.’ I nodded and concentrated on relaxing my ass. This felt very different from the dildo that we called ‘our friend’ there was significant heat, the texture, and the fact that it was an actual cock, that was moments away from penetrating me, the first time in my life that this would be happening.
I felt pressure building, and the head of Ray’s cock working inward. I breathed, relaxed, breathed. He continued pressing, slowly as he had said, and my sphincter began to accept the dark invading flesh. My breathing had increased considerably, and I tried hard to remain relaxed, but this was more, there was more moving inside of me, this was more intense, it began to feel as if I’d tear back there, and my eyes went wide.
‘It’s okay Baby Girl, Daddy’s gonna go slow..’ Ray whispered to me. I nodded, and the pain continued to spread. It felt like my asshole was on fire, I wanted this to feel incredible, and at that moment, I only felt pain, and fear. I clenched my eyes shut as Ray held still, waiting for me to adjust to his size. Then I felt a soft hand take my own hand, and hold it. I opened my eyes, and saw Amy kneeling next to the bed, she brought my hand close and kissed it. ‘It’s okay Kim, I’m right here.’
I nodded and began breathing once again, willing myself to relax, but the pain kept me tense. Ray move a bit deeper, and Amy looked up at him, and quietly said ‘She needs a little more time.’
He nodded and held still. Amy ran a hand across my cheek ‘It’s okay Baby, just relax, just focus.’ I nodded once again and closed my eyes.
‘This is her first time.’ I heard Amy say. ‘That’s right, you’re her first Ray, and I want you to fuck her real good, I want to watch your balls slapping against her ass, and I want to her her plead with you to fuck her harder..’ her voice sounded so innocent, yet her words.. ‘But she needs some time to get used to that big black cock of yours.’ God, her words dripped of sex. I opened my eyes and noticed Ray wasn’t looking down at me, he was looking at Amy.
Her hand left my cheek, and rested on his shoulder ‘Just let her get used to you inside of her.’ And then she leaned in and kissed him.
I wasn’t sure what was happening, we’d never discussed this. I didn’t want to seem greedy, but Ray was here for me, and now my Girlfriend is kissing the guy that had his cock in my ass. I watched dumbfounded, as Amy broke the kiss, then looked at me sweetly, and asked if I was okay, while she stood and began taking her clothes off.
My eyes went wide, and I felt Ray squeeze a bit more of his cock into me, if it hurt, I couldn’t have told you, as I had become transfixed on Amy, who was now naked, and had knelt back down next to me, and took my hand in hers once again. I watched her watching Ray, and she asked without looking towards me ‘Still Okay Baby?’
I nodded, then said ‘Yeah, it’s not as bad now, just go easy Ray.’ and I felt more of Ray sink into me, by this point, I truly felt full, if I’m honest, I felt a bit proud that I’d managed to take so much cock, I hadn’t thought he was much bigger than our friend, but he felt much, much bigger with as much as he had inside me at that point.
Amy squeezed my hand to reassure me, but then leaned back into Ray, and they kissed once again, more noisily, it was almost like they were devouring each other. Imagine how crazy it is to feel jealous at a moment like this. Ray had his cock in my ass, and I was feeling jealous, maybe threatened, maybe both, because my Girlfriend was kissing the guy trying to fuck me.
Almost as if Amy had read my mind, she broke their kiss, and then kissed me softly ‘I’m sorry Baby, just watching you two, turned me on so much. I hope it’s okay?’ she asked.
Ray sank more of his cock inside of me, and then he had no more to offer. I had all of it inside now, I heard his moan ‘Damned Baby Girl, you got it all inside.’
I looked away from Amy, and up at Ray ‘It feels like that big cock of yours is going to split me in half.’ I only half-joked.
He flashed that big smile of his and said ‘Something tells me you’ll be just fine in a few more minutes.’ and he began slowly moving out of my ass, then moving back in, I could feel his balls on my ass, and it made me feel like a complete Slut.
‘Amy, he’s balls deep in me Baby, I can feel his balls against my ass..’ I moaned.
Amy kissed me again, and held my head ‘That’s my girl, just relax, let it happen, enjoy it..’
I closed my eyes once again, relaxing had become easier, and Ray was now withdrawing nearly all of his cock before sinking back into me slowly. I moaned softly, between the thought of a Man actually fucking me, having an actual cock inside of me, and the feelings that had begun to develop from that fucking, I allowed myself to drift further, to allow the pleasure to replace the pain that had been there only moments before.
‘You look so good, Baby.’ Amy said. ‘You look so Sexy getting fucked like this’ she stood, and moved behind Ray, kneeling, and watching his cock moving rhythmically in and out of me.
‘It feels soo nice..’ I said ‘His cock is stretching me out, but it feels soo nice.’
‘Baby, I’m watching his cock fuck you, you’re taking all of it, you’re taking all of his big black cock.’ she said proudly. I could see her moving her hand, but couldn’t see she had cupped his balls, as they swung back and forth as he fucked me. ‘His balls are so heavy Kim, I’ll bet he fills you up so good when he cums.’ her voice filled with lust.
Ray had begun actually fucking me at this point, and I lifted my arms to pull him closer to me, he leaned forward, his chest pressing hard against my tits. I reached under his arms and pressed my nails into his strong back, and whispered ‘That’s it, Lover, give me that big cock of yours..’
He grunted and began fucking harder, and the waves of pleasure in my ass began building, feeling similar, but not exactly the same as what I’d felt when Amy was using our dildo on me.
Ray lifted off of me, and I felt his cock slip out of my ass, which immediately felt empty. I looked at him, and he knelt ‘Get on your hands and knees’ he said. I rolled over and assumed the position in front of him. Amy was kneeling behind him and stroking his cock from behind, her face wore a mask of lust.
I spread my legs apart, and arched my back for him ‘Is this okay Baby?’ I looked over my shoulder and watched and he moved forward. I could see Amy still holding his cock.
‘Let me put it in her.’ I heard her say. I felt the head of his cock at my entrance and then felt it wiggle up and down, no doubt Amy teasing me. I moved my ass back, hoping to press Ray inside, but Amy was having none of that.
‘What do you want?’ she asked.
‘I want his cock.’ I quickly answered and wiggled my ass.
‘You want his what?’ she asked again.
‘I want his big black cock.’ I moaned.
‘Where do you want his big black cock Kim?’ she continued to tease.
‘I want his big black cock in my ass..’ I hissed.
And then I felt my ass open, as he pushed the entire length of his cock into me. Ray began a steady rhythm, and the pleasure began building inside of me again quickly after. Amy moved to the end of the bed where my head was, and kissed me deeply, forcing her tongue into my mouth, moving it in and out, like a little dick, and it just added to the moment. Ray had ahold of my hips and was thrusting into me, making it harder for Amy to continue our kiss, she stood and said ‘Fuck her from behind, on her side.’
Like that scene we’d watched, I thought.
He pushed me onto my side, and slid behind me, moving his cock into position. Amy stood in the doorway once again, watching. I gasped as he found the mark and sank himself fully inside of my ass. I watched Amy, as she watched me getting fucked. She had a glazed look in her eyes. I knew she was thinking of the scene we’d watched, but Ray wasn’t making love to me, he was fucking me. Which I was perfectly fine with. He took hold of my hip and pulled me back as he thrust into me, and Amy watched transfixed. Her hand moved to her pussy, and began rubbing.
‘You like it this way?’ Ray asked behind me.
‘Fuck yes, your cock feels soo good inside me Ray.’ I moaned.
‘You feel good too Baby.’ He sighed. ‘Your Girlfriend must like the view huh?’ he asked.
My eyes never left Amy’s, and her eyes never left mine ‘Yeah, I think she likes the view.’ I could see her breathing become more labored, and her hand moved faster across her clit. I just let it all happen, and surrendered to Ray’s cock which was now easily fucking into my stretched-out ass. I let the feelings flow through me, this felt incredible. Amy’s moans got louder, and from deep inside of me somewhere, I felt a long-missed pressure start to boil over, I let it happen, I let Ray’s incredible cock push me over the edge.
‘Amy, I’m.. cumming..’ I gasped and felt my orgasm overtake me. It hit like a freight train. I looked down, and like scene, we’d first watched, my flaccid penis, was spurting cum everywhere, I looked over to Amy, and she was convulsing in her own orgasm, we were cumming at almost the exact same time. Meanwhile, Ray kept pounding that magnificent cock deep inside of me ‘Gonna cum soon Girl.. Where do you want it?’ I looked at Amy, her face lit with excitement.
‘Cum inside her..’ she said, not hesitating.
Raw gripped my hip and slammed his cock into me, and with a deep growl I could feel his hot cum inside me, I ground back against him wanting more of him inside, and wiggled my ass against him.
A few moments passed, then Rays cock slipped from my ass and we lay there recovering for a while. Amy knelt next to me and stroked my cheek again and kissed me ‘I’m so happy for you Baby..’ she said.
I kissed her back ‘Thank you, Amy, thanks for letting me do this.’
She rolled on top of me, and gave me a quick kiss, and then at Ray and said ‘Okay, so are you ready for round two Loverboy?’
Ray’s low whistle filled the room, the night was long from over.