I’ll get around to telling how the last twenty minutes of the first story finished at some point, but it suffices to say, it was awkward. Abby and I drove home without speaking and went to bed without speaking. I didn’t know how to feel. Was I mad? Maybe at the overall situation, but I suggested the night. I really couldn’t be “mad” at Abby. She obviously had a mind blowing experience. I didn’t want to ruin that for her. In the true meaning of “swinging”, we both had sexual relations with other people, and were consenting in the play. But that didn’t change the fact that the experience was VERY different from how we both imagined that night going. I felt as though it went terribly for me, and exceptionally well for her. Like in a way that scared me for our relationship.
After 4 hours of terrible sleep, I decided to get out of bed around 6 in the morning. As I walked past my sleeping wife, I couldn’t help but think she looked beautiful to me still. I sat in front of the TV and watched some nameless basketball game on ESPN Classics. Just before 9, Abby walked in the living room. She still looked tired, but I couldn’t help but notice she had a glow to her. She came and sat next to me on the couch and rested her head on my shoulder. We sat together for 15 minutes in silence.
“Are you ready to discuss last night, babe? Abby asked. “If not, I understand.”
“I’m not really sure what there is to discuss.” I replied somewhat coldly.
“Ok. I don’t want to push the subject if you aren’t ready.” Abby calmly said. We both knew there was tension in the room.
“Was he that much better than me?” I asked point blank.
That question took the tension up by tenfold. I could feel Abby squirm with her head on my shoulder. She sat there for 45 seconds before she responded.
“I don’t know how you want me to answer that.” She replied
“I think it’s a pretty straightforward question Abby.” I said.
“If you want a straightforward answer, then here it is. I have never been fucked like that before in my life.” Abby sat up and turned to look at me.
“Ok.” I quietly replied. “So what do we do from here?”
“I don’t see why this has to change anything. It was an experience. I know my experience was vastly different from yours, but that doesn’t change the fact that I love you completely. I’m hoping that it hasn’t changed the way you feel about me.” Abby explained.
I didn’t know how to respond, so I sat there sulking.
“I love you.” I finally replied. “I still love you. But you were different last night, and it scared me. Obviously the night went nothing as expected for me. I thought we would find a kinky couple and have fun. Eden didn’t want anything to do with me. The whole dynamic was weird. I felt like she used me, to get to you, but for Reggie. I didn’t understand that dynamic at all. What was in it for her, other than maybe she got off on humiliating me? I just can’t make heads or tails of anything that happened from the moment you left the bar with Eden.”
“Yeah, I’m not sure what their story is.” Abby said
“Do you want to see him again?” I asked sheepishly
“I’m not sure that’s a good idea.” Abby replied
“That wasn’t what I asked though.” I coldly said again
“I don’t want anything to change between us. I had the experience, and while it was great, I’m fine with it being a one time thing. Besides, Reggie is going out of town for a couple of weeks anyway, so it’s not even up for discussion.” Abby told me
“How do you know that?” I questioned
“He texted me this morning to see how we were doing. I think he felt bad about last night. He was concerned for you.” Abby said
“Well that’s bullshit. He knew exactly what he was doing from the moment he sent Eden over last night. He has done that before to other couples, I’m sure of it.” I quipped back.
“I’m serious. He was concerned. He was upset with Eden and how things went with you two. He wants to make it up to you.” Said Abby
“Make it up to me? What does that even mean? And the set the record straight, I never want to see Eden again in my life.” I said, now starting to get angry. The nerve of this guy.
“He wants you to be able to have a night with Samantha. That sounds pretty hot, right?” Abby said.
“See, that’s what I mean. This makes no sense Abby. Who is this guy. He feels guilty about fucking your brains out, so he sends over a young girl to calm me down? You don’t think that seems odd?” I asked
“I don’t know Anthony. I don’t know anything about this lifestyle. This was all your idea, I might remind you.” She said, her voice raising.
We sat there, just looking at each other for a few minutes. I didn’t know what to say anymore.
“Was she cute? Sam that is.” Abby asked
“Sam was hot.” I said with enthusiasm, trying to make a jab at Abby.
“I want to watch you with her.” Abby said, sliding back next to me, moving her hand on to my thigh.
“Let me think about it for a couple of days. If I feel up to it, we can set up something next weekend.” I said
Abby ran her hand under the leg of my boxer shorts, and began massaging balls. “Sam wants to come over tonight. I figured you would be interested. She can be here at 9.” She continued rubbing, with my dick quickly hardening. I don’t know why, but my thoughts flashed to the previous evening thinking about how hard I was watching Abby submit to such a huge cock.
Trying to quickly change my thoughts to Sam’s tits, I replied “That sounds perfect, set it up and tell her to wear something sexy.” I tried saying it as confidently as possible, but I’m not sure it came across that way.
“Will do baby.” Abby said, as she pulled her hand out from my shorts, grabbing her phone to text Sam. I was hoping she would go back to rubbing, but she hopped off the couch and went to shower.
The rest of the day was somewhat awkward. Abby and I were cordial to one another, but I was a bit nervous about the coming evening. I kept trying to picture Sam laying on my, rubbing her beautiful boobs on my cock, but my mind would immediately flash back to that moment that Reggie entered my wife, and the gasp she took. I couldn’t get it out of my head. It was so powerful. We cooked dinner together and sat on the couch to watch a movie. I was watching the clock every minute it seemed. I secretly hoped that Abby would get jealous tonight and this would be the end of our swinging experiment and our lives would return to normal. Just like the previous night though, I couldn’t have been in for more of a surprise.
Ten minutes before 9, there was a knock at the door. Sam was early. My stomach jumped a bit. Abby got up, and walked to the front door. I could hear her and Sam trading pleasantries. They walked in the door, and I was blown away. Sam looked fucking hot. She had on tight leather pants and a corset that was pushing her amazing tits almost up to her chin.
“Hi sexy!” She exclaimed excitedly while giving me a hug.
“Hey!” I replied. “Great seeing you again so soon. I figured you might need to recover a bit from last night.” I said, while picturing Eden with that ridiculous strap on, which again made me think of Reggie’s cock.
“Nah, I’m always ready for some more fun!” She said. Sam’s personality was great. It again made me wonder what the dynamic was between her, Eden, and Reggie. He seemed to hold some sort of power over all these women.
“So last night ended up being pretty hot, right? Sorry if I barged in on your fun though.” Sam said
“Not sure about that, but you were definitely my favorite part of the whole night.” I said slyly, again, trying to take a bit of a jab at Abby.
“Awww, that’s sweet. I could tell how much you loved these tits by that huge load you blew on them.” Sam replied, slowly snaking her finger down between her cleavage.
“They are incredible baby,” I commented. In the back of my head though, I knew that at the moment I actually came I was barely even aware of her tits. I had been fixated on Abby’s moans, and wondering just how deep in her Reggie’s cock was penetrating.
“Let’s have a drink to get everyone loosened up a bit, whaddya think?” Sam asked. That’s an easy comment to make for a girl in her 20s. At 38, the shots last night back to back, plus the drinks we had when we got there, I was still feeling it some from last night. Not wanting to be the party pooper though, I agreed.
I went into the kitchen to see what I could scrounge up. As mentioned, I was hoping to make Abby jealous, but Sam was just too nice. I could already hear them laughing it up together in the living room. After looking through the entire kitchen, all I managed to come up with was tequila again. The thought of shots again didn’t sit well with me, but there wasn’t much choice. I grabbed some glasses and the bottle and walked back in the living room.
“You just walk around all day with all this stuff???” Abby was asking Sam while sitting on the floor digging through her bag.
“Well, not all day, but there’s no reason to not keep a vibrator around for if you have some time to kill, if you know what I mean.” Sam winked at Abby
“And this?” Abby said, pulling out a set of wrist restraints
“There is a time and place for everything. If you’ve never been tied up, you have NO idea what you are missing. Stop digging for now though, I don’t want to ruin all the surprises.” She smiled wickedly over at me.
“No problem” Abby said, “I’m just a bit in awe of your sexuality at such a young age.
“I was a total nerd in school. Pencil thin with huge boobs I was embarrassed by and horribly curly hair. Everyone made fun of me. I was obsessed with sex though. It wasn’t until college that I blossomed a bit. Luckily I grew up in the age of online porn and really learned my power as a woman, and used it to expand my horizons. I don’t mind telling anyone how much I love sex.” Sam explained to Abby.
“Hey, I’m easy. I don’t need to expand my horizons. You riding my cock while I watch those beautiful boobs bounce is more than enough more me.” I said somewhat jokingly, setting down the bottle and glasses.
“Uh huh. This is going to be a night you don’t soon forget mister. You wouldn’t last more than 5 minutes if I just hopped on you.” Sam said flirtatiously.
That was true. I did have concerns on how I was going to perform tonight. I wasn’t sure how I was going to compete with Reggie, or even Reggie 2, as they called it. It made my stomach jump a bit again.
We poured ourselves shots and took the first one. It definitely stung a bit. I could see it in Abby’s eyes as well. Sam thought nothing of it though. She immediately poured the next round. The next shot was a bit harder to keep down. Sam was ready for a third, but Abby and I declined.
“Oh fine, boomers!” She said jokingly. “Let’s get started then. Take your pants off mister.”
That was an unexpected. I wasn’t even hard yet. I was more of a grower than a show-er. My mind immediately flashed back to first seeing Reggie’s cock. It had to be seven inches long when it was limp. There was no way I was going to impress these two. Oddly though as I unbuttoned my pants, I could feel myself starting to get hard. Sam was on her knees now and moved toward me. She grabbed my boxers and pulled them down swiftly. My quickly hardening cock popped free.
“Mmmmm, do my tits make you hard?” She said?
“Yeah baby” I replied, not really sure of myself. Being honest with myself, I wasn’t sure if it was her tits, or reflecting back on first seeing Reggie’s cock.
“Sit back on the couch then scoot forward.” She commanded, pretty directly this time.
She pulled my pants and boxers off, leaving me naked, except a shirt on. I looked to my right, and saw my wife, seemingly enjoying the show. Sam pushed my legs apart and ran her hands up my legs, just teasing my crotch. I was rock hard now. I was definitely turned on, but still nervous knowing the cock they had both had last night.
“Stroke my big cock baby.” I tried saying as commanding as possible. It fell flat though. Instead of me taking control of the situation, both Sam and Abby just giggled. It stung a bit.
“Calm down, stud.” Sam replied. “You just let me lead tonight, and I’m going to blow your mind.”
Stud. That brought back thoughts of Eden. Definitely not where I wanted my mind wandering right now.
Sam started digging through her bag looking for something. She pulled out a bottle of lube, popped the lid, and slowly drizzled cold liquid on the underside of my dick. It jumped a bit from the sensation. She then turned the bottle around and squirted lube all over her chest. She began massage the lube across her cleavage with her left hand as she grazed the top of my dick with her right thumb. The teasing was intense. She was certainly well versed in her teasing. At that point, she grabbed under my legs and pulled me further off the couch. It was a bit awkward, as I was having to hold myself up some. She darted her head between my legs quickly and lightly flicked my balls with her tongue. Again, my dick jumped at the sensation.
“You’re so excited baby. I love watching your dick twitch like that.” She said. She sat up some and placed her hands on both of my knees. Her hands were slick at this point. She slowly pushed them forward. My dick ached. I wanted her to stroke it badly. As she got closer though, she spread her arms wider, and slid her hands on to my stomach. At this point her tits were starting to press against my crotch. She lifted up some as I watched her slide her perfect cleavage along the underside of my dick. Her well lubed boobs and my well lubed cock glided softly across each other. Her hands continued up to pecs and on to my shoulders. As she began sliding her boobs back down my dick, she rubbed the palms of her hands across my nipples. She then stopped and gently pinched them. My cock jumped again. Abby and I had always ignored my nipples, but the gently pinch felt oddly satisfying.
“Ohhh, you liked that, didn’t you?” Sam asked. She looked at Abby. “He likes his nipples pinched, doesn’t he?”
“Well, I guess I don’t know. I’ve never pinched them before.” Abby replied, sitting up and looking more intently.
“And you’ve been together how long? This many years, and you don’t know every spot on his body?” Sam’s voice had a bit of a tone to it with that question.
“I guess. Well, I’m not sure, that we ever, I mean I guess we’ve never tried that.” Abby said, sounding almost embarrassed.
Sam looked at me and asked, “You want me to do that again, right?”
“Yeah, I think so. I mean, I didn’t mind it.” I replied
“Anthony. Yes or no. You know whether or not you liked it. Now is not the time to start being timid.” She said matter of factly.
“I liked it.” I replied
“Good.” And with that, she began massaging my chest heavily with her palms, pressing deeply on my nipples. After a few rubs, she pinched them again, but this time for longer. The feeling was amazing. She was right. I was 38 years old. How was I just finding this out?
Sam continued to massage my chest and pinch my nipples, all while sliding her tits over my cock. The full body pleasure was amazing. Just like that though, she pulled back and took hold of my dick. She wrapped her hand around it completely and started circling her thumb on the underside of the head. I squirmed uncontrollably. I looked at Abby. She seemed fascinated by the entire scene.
“I’m ready to fuck your tits again before I pound you.” I said. I felt like I had to say something because the teasing was just too intense. I was super horny and not used to this type of sensation. On one hand, it felt amazing, but on the other I was just used to getting hard, and then cumming. I wasn’t used to the woman being in control of my pleasure in this way.
“I already told you to calm down. The night is young.” Sam replied.
The night was young, but I wasn’t so much anymore. With much more teasing, by the time Samantha and I got to the actual sex, I would probably blow my load in 20 seconds, and that would be it for the night for me. I wasn’t sure how old Reggie was, but he seemed around my age. How he expected to get off three times the night before was beyond me.
I tried playing it off. “Mmmm, yeah it is sexy. You can keep playing.”
Sam had a ninja grip on my dick with her right hand. She lifted her left hand up under my balls and cradled them, kneading them gently. She lowered her head, and again, gently grazed her tongue against them. After doing this for a bit, she flipped left hand over and pressed directly on my taint with her thumb. I immediately bucked my hips, thinking I was about to be pushed too far and blow my load.
“Whoa, cowboy. I know what that means. I don’t need you cumming just yet. We have way more to explore.” Sam said. She moved away from my body, giving my time to cool off.
“You liked that too, right Anthony?” She asked
“That was intense.” I replied. I was becoming entranced with this girl.
“Let me guess, you don’t massage his taint much either?” She asked Abby
“I’ve rubbed him there before. Maybe not a lot though” Abby replied.
“You don’t aggressively rub his taint while you tease his cock though, right?” She asked
“No, I guess I’ve never teased him like you are now. I’m learning a lot though. I can’t wait to see what’s next.” Abby said, much more upbeat about the night than I expected.
“I was hoping you would say that. You’re going to think about your husband a lot differently after tonight.” Sam said as she smiled.
Abby wondered exactly what that might mean. She couldn’t help but think about what else could be in store after last night. As she said earlier, she still loved her husband, but she couldn’t help but think differently of him after the mind-blowing sex she had. It wasn’t that Anthony didn’t want that for her, she felt, but the reality was that both Reggie’s confidence, and his cock, just couldn’t be replicated by Anthony. There was just something about Reggie that couldn’t be described. She didn’t think that Sam was magically going to turn him in to Reggie.
“Here they are.” Sam said. She pulled out the wrist restraints. “Anthony. I’m going to bind your hands together. If you don’t like it, tell me so, ok?”
She didn’t really give me a choice. I was still focusing on keeping my pending orgasm at bay.
“Ok, sure.” I had never been tied up before, but I had to admit that everything so far had been great. She slowly slid her body along mine. Her amazing cleavage slid up my balls, along my shaft, and across my chest. Just as she had done the night before, she grabbed my wrists and lifted them above my head. She undid the restraints and put them around my wrists. She attached a second strap around the back of the couch, and pulled it taught. My arm movement was severely limited. It was very intense mentally. I had never been in a situation like this at all. Her cleavage was dangling just above my face, barely out of reach. I tried to lift my head up to lick, but between my ass hanging off the couch and my arms locked above me, I couldn’t do it. As she began moving back down my body, she massaged my pecs again, pressing heavily on my nipples. She moved her right hand back down to my taint and moved her mouth over my left nipple. She pressed and flicked at the same time. She wasn’t even touching my dick, and the pleasure was incredible.
“You already love being tied up. I can tell already, right?” She asked.
I just nodded my head.
“I need you to answer me Anthony.” She calmly, but firmly stated
“Yes.” I replied
“Yes, what?”
“I like being tied up.” I said.
“Ma’am.” She said
I looked at her questioningly.
“I’m going to need you to call me Ma’am from here on out Anthony. Those are the rules if you want to keep playing.” Samantha said.
“Ok Ma’am. I can do that. I like being tied up Ma’am.” I replied. I could feel the tone of the evening changing a bit, but I didn’t think much about it.
“Good boy”. Sam replied. “I have one more thing I want to add.” I didn’t know what they were, but she pulled out a set of nipple clamps. She began adjusting them though, and I quickly understood. She clamped them on gently. The pressure was just right. I couldn’t help but think to myself that like last night, this night wasn’t going anywhere near as planned, but so far it had been absolutely amazing.
“So?” She asked
“I like my nipples clamped, Ma’am.”
“Ohhhh, good boy!” She replied. “You’re a quick learner.”
She moved back down between my legs and began rubbing all around my crotch, constantly pressing on my taint. I couldn’t believe how sensitive my entire body had become.
“Are you having fun tonight, Anthony? Are you enjoying this so far?” She asked
“Yes Ma’am. I can’t wait to fuck you Ma’am” I replied
“That’s not going to happen Anthony. Sorry to burst your bubble. This might be a sting to your ego, but there’s nothing I would get out of you fucking me. I need to be proper fucked, remember? If that’s ok with you though, I do promise that you’re going to have the most intense orgasm of your life tonight.”
That did sting my ego. I knew deep down that I couldn’t compete with the cock she was used to, but I didn’t like hearing it, especially after Abby admitted that Reggie was the best fuck she had ever had earlier this morning. Again though my thoughts flashed back to the previous night and how incredible the orgasm I had was while watching my wife get fucked. At this point I felt I had nothing to lose, even though my ideas of making Abby jealous were tossed out the window now.
“Ok.” I said, sounding somewhat defeated.
“Ok, what?” She replied
Ok, Ma’am.” I said.
“Thank you. Now, on to the good part. You are enjoying this so far. I’m really enjoying this too. You trust me right, Anthony?” She asked as she was re-lubing her hands
“Yes Ma’am, I trust you.” I replied.
“Good.” And with that, she grabbed my cock with her left hand and slid her right hand directly up my ass crack, and right across my asshole.
I flinched aggressively trying to squeeze my ass cheeks together, but my legs had started tiring from holding up my weight for the last twenty minutes. I didn’t know what to do. This was out of my comfort zone entirely. I had no interest in ass play at all, but while I flinched instinctively, there was also a sensation that shot through my body. My nipples doubled in hardness.
“What are you doing?!?!?” I asked “This is too far.” I started saying
“Shut up Anthony.” Sam said. Her tone was decidedly more demanding now. “I just told you that I was going to give you the best orgasm of your life. On top of that, I’m nice enough to let your wife, who seems to know very little about what you actually like, watch, so she can give you the same pleasure. If you don’t trust me, tell me now. I will go.”
I looked to Abby, but she was dodging eye contact with both Sam and I. Everything from the previous night came rushing back. I instantly hated Ray and Steph again. Could I really tell him I let this girl tie me up, put nipple clamps on me, and then try to massage my ass though? The whole scene was a bit over the top at this point, and all on my own agreeance.
“I’m not gay.” I blurted out.
“This isn’t about being gay, Anthony. This is about pleasure. I’m promising you pleasure. Whatever walls you have built up around that, I can’t control. I want to show you that pleasure, but it involves my hand and your asshole. That’s the bottom line. You know what you felt just then though, don’t lie. And call me Ma’am.”
She knew what I had just felt. She was a pro. I could tell she had done this before. I couldn’t lie to her, she would see right through it. Just like the night before I wanted to yell out stop, but I couldn’t. I was in too deep.
“Yes Ma’am.” I said, sounding defeated once again.
“Do you want me to massage your ass, Anthony?” She asked
“Yes Ma’am, I want you to massage my ass.” I said, staring up at the ceiling, not believing what I had just said.
“Abby, are you paying attention? I certainly hope you are. I’ve learned more about what pleases your man in the last 30 minutes than you have in your entire marriage. No wonder you two had to come looking for help at the club. Somehow you lucked in to finding Reggie on your first night, but if I was Anthony, I would have left long ago.”
Ouch, I thought. That jab was just as bad as anything I had hoped for tonight.
“You’re right.” Abby said, with her head down.
“You’re right, what, Abby?” Sam replied.
“You’re right Ma’am.”
“Good girl. Now let’s proceed.”
This time Samantha wasn’t nearly as direct. She had full access to my ass and began rubbing her hands all over it. It felt very relaxing and soothing. Every few circles though, she would graze closer to my crack, and I would twitch a bit. I had almost forgotten about my dick, but it was still rock hard. I started loosening up, and the rubbing was oddly satisfying. Sam picked up the bottle of lube again and coated her fingers. With her left hand, but pulled one check to the side, and with the other, but slid her fingers down my crack once again, this time stopping to rest right on my hole. Lightning shot through my entire body.
“Mmmm, you like that. You like me massaging your asshole. I like it too.” Sam said
I didn’t reply. One, the feeling was too intense, and two, I knew if I agreed, I would have to say it all out loud. I didn’t want to do that. She continued rubbing though, and every stroke was like my ass was connected to my nipples. The sensations coursed through my body. The more pressure she gave, the more intense the feeling was. It was right then that I knew what was coming next. I couldn’t admit it though. I just spread my legs further apart for her.
“Oh, thank you Anthony.” Sam said. “I want to finger your ass too!” She said excitedly.
I just laid there. Why did I want this? 10 mins ago I freaked out because I had my asshole touched for the first time. Now I’m spreading my cheeks waiting for her to finger me? I couldn’t explain it though. The sensations coursing through me were incredible. I didn’t know what to say, so I didn’t say anything. I just laid there. I could feel Abby watching the entire scene intently. What was going through her mind right now? 24 hours ago, we were a normal couple that had hit a dry spell. Now she had had the fucking of her life by a huge black cock, and she was currently watching me tied up, wanting my ass fingered.
I could hear Sam snap the lid open on the bottle of lube. She poured it on her fingers and went right back to my asshole. She did this a few times, adding more and more lube each go. Without warning, she slid her index finger inside me. I gasped lightly. We all sat there in silence for a few seconds.
“I find it best to just slip it in when the muscles relax enough. Everyone clinches up if you tell them it’s coming” Sam said
I just nodded. The feeling was odd. I wasn’t sure what to make of it yet. It wasn’t uncomfortable, but also not exactly mind blowing like I had hoped. At that moment though, Sam pressed deeply in me and curled her finger. It was then that I became aware of my prostate. My entire body convulsed. I could feel it through the tip of my still hard dick.
“That’s nothing.” Sam said. “Just you wait. Your prostate is deep in there though, I’m going to need to use my middle finger.”
She slipped out her index finger to lube up more and I immediately missed it. This time around I felt more pressure. She was inserting two fingers. It felt great. As she slid in deeper, the pressure became more intense. Once she was all the way in, I could feel my prostate again. She began manipulating it and it was overwhelming. As she continued, I could again feel it all the way through my dick. I began to precum, but nothing like had ever happened before. There was a lot. It was a constant drip.
“Now that’s a good good boy.” Sam said, as she watched my dick bounce up and down with each thrust.
“Do you like it when I finger your ass, Anthony?” She asked
“Yes Ma’am, I like it when you finger my ass.” I replied.
“Do you still trust me Anthony?” Sam asked
“Yes Ma’am, I trust you.” I replied. I just laid my head all the way back, knowing what was coming next. I didn’t know if this was a step I could take. The stigma was too big.
“Good Anthony. I’m glad you do. Here is where we come to a fork in the road though. You get to make a choice now, and so does Abby.”
Sam was shuffling through her bag with her other hand as she was still fingering my ass. It made it very difficult to concentrate. She pulled out a big black dildo. Not Reggie 2 big, but still, a big dildo. She laid it on my stomach, next to my dick. I assumed to make it clear that it was larger than I was. I glanced down at it, then over at Abby. She seemed oddly excited about this development.
“I want to fuck your ass with this black cock. And when I do, I promise it will fully hit your prostate, and you are going to explode with the biggest, most intense orgasm you have ever had. Your decision is this. Are you ready to go down this path with me, or do you balk? If you say no, I get it. I will pack up and leave now. If I leave now though, Abby is not allowed to finish you off. At least not if she ever wants to get fucked by Reggie again. She has to keep you tied up here overnight.”
My head started to spin. Was Abby really going to fuck Reggie again? That hadn’t even been discussed tonight. Why was Sam mentioning that? Could I really take this cock in my ass? I mean, I was sure that I “could”, but should I agree to this. I was so far beyond horny though. I didn’t feel like I could think straight in my current head space. Should I really be making this decision all over an orgasm? I tried looking to Abby for guidance, but as soon as Reggie had been mentioned, she had looked away. I felt like there was something she was hiding from me. If I said no, and she couldn’t fuck him again, would she just leave me? I knew I could never give her what he had. Would the lure of his powerfulness be too much for her?
I also felt somewhat tricked by Sam. She had started out so hot, but innocent seeming. This had been her plan all along. This had been Reggie’s plan all along. At the same time, I felt like Sam knew me. She presented all of these things to me in a way that made me open to them, and so far, I was loving it. I was even liking the humiliating parts oddly. Eden was doing her best to humiliate me the evening before, and it was a total turn off. Sam seemed to have a way about her though. In this very moment though, I really felt stuck. Just like the night before, I decided to just say “Fuck it” and see what happened. And just like the night before, if only I knew where that would lead…
“I want you to fuck my ass, Ma’am.” I said, my voice cracking like a teenager
“With?” Sam said
“With that black cock, Ma’am.” I choked again
“Good boy. This go around will be a bit different. I’m going to go slow, but don’t clinch. Push back against the cock and it will slide in nicely.” Sam gave instructions while lubing up the cock. I was nervous. It had to be almost seven inches long. Not super thick, but compared to the 2 fingers that just came out of me, it was huge.
Sam re-lubed my crack, and slowly rubbed the head of the cock along it. When she found my hole and started to push, the sensation was entirely different. The pressure seemed immense, and caused me to clinch.
“Relax. You know you want this black cock deep in your ass baby.” Sam said
I did want it. And hearing her say it did relax me. I nodded my head, and she pressed again, this time with more force. I could feel myself opening up. She kept steady pressure and I feel my body accepting it. After just a few seconds, it was in. Not far, but it was in.
“This is my favorite part!” She smiled slyly. “I love taking virgin ass!”
Just like with the first finger, the feeling was awkward. I felt my ass wrap around the cock, but there wasn’t much sensation. Just like the last time though, Sam knew what to do, and she slid the cock deeper in me. This time, the head of the cock pushed fully on my prostate, and I gasped loudly. In my head, I couldn’t help but think that my gasp was eerily similar to my wife’s last night when Reggie filled her with his cock. Was this what it was like for her? Is this what it felt like to take a big cock? My prostate was completely full from the past hour of teasing. Fluid shot out of my dick.
“Oh my god. Did you just cum from that cock in your ass?” Abby stared wildly at me. She was fixated on my spasming dick.
“That’s just prostate fluid. The real fireworks are coming soon enough.” Sam explained.
Had I just cum? I never experience anything like that before. My dick was spasming like I was orgasming, but the sensation didn’t die down. It just stayed constant. Sam began moving the black cock in and out, with each stroke going slightly deeper. I felt a fullness inside of me that I never expected. Each long stroke massaged my prostate more and more. After just a few minutes, I was in total bliss, and the cock was fully inside me. The puddle on my stomach had grown a lot. Sam had milked me dry I thought, but with every pass, more and more fluid came out. I never wanted it to stop. It was like a 3-minute-long orgasm.
“That’s it. That’s my good little sissy.” Sam said, very matter of factly. 15 minutes ago, that would have been too much. I would have called time out and ended the night. Now, because of Sam’s gentle manipulation, I didn’t care at all what she called me. I just didn’t want her to stop.
“Do you love this black cock in your sissy ass, Anthony” she asked
I might not have cared if she called me that, but I wasn’t quite sure I wanted to say it just yet. I just nodded in agreeance.
The stroking came to a stop. I felt empty all of a sudden.
“I didn’t hear you, sissy.”
I hesitated.
“I said, I didn’t hear you, sissy.” Sam slowly started pulling the cock from my ass.
“I love that black cock in my sissy ass, Ma’am. There, are you fucking happy? I love it.” I really was annoyed. I was annoyed that she was making me say that out loud. I was annoyed that I was admitting it. But I was mostly annoyed that she had stopped fucking me with it.
“Rarrr!” She immediately quipped back. “You’re a sassy little sissy aren’t you. How hot is that. You love this cock too much to not say it though.
I didn’t reply. Luckily she didn’t make me. She just went back to fucking me. Pounding me really. She was become more forceful, and all the while, the sensations were become more and more intense. It was literally unbelievable. There were so many things going on all over my body that I couldn’t keep track. My nipples felt like they wanted to explode. My ass wanted more cock, harder and harder. My dick, it just kept dripping precum. It really did feel like it was going to explode though. Every press on my prostate shot directly through to my dick. It was 3 times as intense as an hour ago when Sam was rubbing her thumb across the head.
“Ok sissy, I’m going to need you to cum for me. I’m going to need that little dick to explode. I need you to think about how you got here tonight. Tied up, clamped nipples, exposed ass, taking a big black cock in your ass. You need to realize you agreed to all of this.”
Sam was really turning the humiliation up a notch. I couldn’t explain it, but it was really turning me on.
“You wanted this. All of this. 3 days ago, you didn’t know who you really were. Now you know. You’re nothing but a little dicked, cuckold sissy. Your wife is sitting here watching all of this. She’s watching your reactions to all of this. She is never going to look at you the same. She got what she needed last night. She got 9 inches of black cock, fucking her hard. And now, she’s watching you get exactly what you need. Big black cock, filling you too. You’re both the same. You’re both total sluts to black cock.”
She was furiously pounding my ass. I was completely lost in my head, gripping at the couch last night, just like Abby had been gripping at the sheets with Reggie pounding away at her.
“Both of you, admit it. Admit what you are right now!” Sam practically shouted at us.
Neither my wife, or I hesitated.
“I’m a total slut for black cock.” She exclaimed loudly
I’m a total sissy for black cock.” I said loudly
And just like that, I came. I shot stream after stream of jizz all over my chest. When I was done shooting, Samantha pulled the cock out of my ass. I partially collapsed off the edge of the couch. My legs were exhausted, but I was still tied to the back of the couch. I was spent.
“And that is what it looks like when you cum from a cock in your ass, Abby.” Sam said. She quickly started gathering her things. “Look, I think you all have plenty to talk about. I’ve had my fun. I’m going to get out of here.”
And with that, Sam picked up her bag, and made her way for the door. Neither Abby or I said a word. I just laid there, exhausted. Reality had started rushing back. I didn’t know how to feel. I don’t think Abby did either. We both knew what had transpired in the last 24 hours, and we both knew the last comments that we had just uttered. Our lives were never going to be the same….