Chapter 01: Our First Threesome
My wife and I had been married for only two years and had talked about our sexual preferences greatly. Before getting married we had been somewhat active but had never ‘sealed the deal.’ Still, what experience we did have with each other made it less awkward for us to talk about our sexual fantasies and what would make us feel fulfilled in the bedroom. Sharayah slowly but surely opened up about her willingness to perform oral sex, her desire to eventually be able to finish me off with oral attention and even to swallow. She admitted an interest in anal sex, and especially in double penetration. We had even talked about affording her the opportunity for the attention of more than just two men and she had responded lustily, showing that a deep, carnal portion of herself was excited at the prospect of being shared by a group of men. We had exchanged text fantasies, always in the realm of the theoretical, about her being double and triple penetrated, or even having all three holes filled while stroking two other men (and potentially even surrounded by more). All of this excited her, but the idea of moving it from the theoretical and potential into the actual was where she balked. She had been raised in a conservative Christian household and was afraid that adding a third party to sex would be crossing a line that could never really be uncrossed.
After we got married, she opened up even more, allowing me to take pictures of her topless and eventually nude, and even during our sexual playtimes as she was riding me or sucking my cock. Having pictures of my sexy young wife performing for me were a huge turn-on and a great help throughout the day when she wasn’t around to assist me sexually. By this point, two years after our wedding, Sharayah was 26. She was still every bit the knockout I had met in college: blonde, blue-eyed, 5’1″, 120 lbs, and slender but curvy with a pair of huge 34DD’s proudly topping off her chest. While her eyes and her wit had been among the first things I noticed and was attracted to about her, it was those DDs which first grabbed my attention. On such a small frame, how could they not? I, like my wife, am blonde and blue-eyed but stand at about 5’10” and weigh about 185 lbs. In our early courtship Sharayah revealed she had never so much as seen a man naked or even seen a penis outside of sexual education courses. When she finally felt my bulge she was pleasantly surprised at the size of my 7″ tool, happy to find that, while not huge, I was above average in that respect.
Upon getting married, one of the first kinks that I revealed was my desire to fuck her breasts. She responded favorably and soon, titfucking had become a regular part of our love-making. We graduated from that to simulating vaginal and oral stimulation with her sucking on a finger while riding me or me fingering her while she blew me. Then, for our first anniversary, we tried a simulated triple penetration and the sounds I heard her make have never left my memory. It was clear to me then, and in the months to follow, that my wife was deeply interested in having multiple sex partners. But how to break through that barrier?
Later in the summer, I bought a sex toy. I spent the morning teasing her and showing her pictures of my own equipment and then jokingly referred to another of her kinks: interracial sex. She blushed and said that she had no real desire to sleep with a black man because she only wanted me but I knew that, again, at least theoretical interracial sex would be within her interest. By the end of the early afternoon I had teased her via the phone with the idea of a black sex toy and she was surprised by how realistic the pictures I sent appeared. I stole away to the local sex shop and bought a black dildo roughly the same size as my own equipment, though slightly shorter and thinner. That night she moaned and squirmed under the ministrations of my own cock and the faux black cock, feeling an even more realistic double male experience and revealing even more that her innermost sexual desire was to be had by two men at once. A few months later I decided to start poking at another fantasy of hers: having an experience with an even larger cock than mine. She blushingly revealed that she wouldn’t turn down a bigger cock and again, I stole away to the sex shop and returned with another toy slightly thicker and a few inches longer than my own. Later that day, though, she confessed that anything larger than my own cock would intimidate her and she wasn’t sure she could bring herself to go forward with it.
Rather than simply trying to coerce her, I decided to trick her. I knew my wife and knew that she would end up loving an even longer and thicker black cock (even a fake one). That night I made sure our bedroom was pitch-black, though, before the lights went out, I made sure she saw our original dildo sitting out on my nightstand. As usual, once the lights were out I was eating her pussy and she was moaning as I brought her to orgasm after orgasm. My oral skills are a point of pride and it’s no exaggeration for me to say that I’ve made her cum over a dozen times in one session just with the use of my tongue, leaving her begging for cock by the time I decide to fill her. After I had been eating her for a bit I focused on sucking on her clit and slid our normal dildo into her wet and ready hole. She moaned as she came from the stimulation of her clit and the penetration of her pussy. I fucked her that way a bit longer and then reached under the bed, pulling out the new, bigger dildo. Moments later I switched back to oral and then a few minutes after that, I inserted the larger cock. She began reacting violently and lustily as the huge piece slid into her, stretching her ever-so-slightly more than my own cock. As I heard the even more fulfilled noises she was making I was more turned on than ever.
After a few orgasms being fucked missionary-style with that bigger cock I grabbed the old dildo and slid up her body, still fucking her with the new one. As I slid the original dildo into her mouth, her eyes opened wide as she realized there were two toys in play. A few orgasms later she was spent. I told her what had happened and at first she was a bit shocked that I would trick her, but when I shared that I heard the fulfilled noises she was making, she nodded in admission and asked to see the new cock. Grabbing her by the ankles I pulled her off the bed onto her knees in front of me, my cock hanging in her face. She leaned forward and took my cock into her mouth as I reached over and turned on the light. I stood in front of her, my cock in her mouth, with one of the dildos in each hand. Her eyes went wide as she saw the size of the new one and let my cock slip from her mouth and asked how on Earth I expected her to take one so big and that there was no way it would fit in her. To be fair, the toy is only eight and a half inches long and only slightly thicker than myself but for such a short and thin girl, it seemed too big. I told her that she had taken all but the last inch of it and her eyes widened again, surprised.
After that night, the two dildos became part of our lovemaking and it wasn’t uncommon for her to ride my cock while the larger dildo slid between her tits and the smaller fucked her mouth. She was getting into being fucked by three cocks at once. She even began to take both cocks into her mouth at once and finally, one day, while the smaller dildo fucked her pussy and the larger fucked her tits and mouth at the same time, she moaned out how much she loved big black cocks. Mission accomplished.
Shortly thereafter I set about preparing to work on the next kink: anal penetration. We had played with her taking a finger and almost a second but she had never gotten the nerve to really prepare to take my cock. One day I finally went back to the sex store and picked up a smaller, thinner dildo (laughably small, actually), and a bottle of KY and that night, while she had the average size dildo in her pussy we began to set about having her take a smaller cock in her ass. After minutes of slow, gentle pressure, coupled with vaginal stimulation, the small cock slid into her ass. The first time hurt her but eventually she was gently taking that small cock in her ass. She wasn’t loosening up quickly but I had no doubt that eventually she would take my cock in her ass. We took a break from the anal play for a while after that and returned to group stuff. She and I (and the dildos) pleasured her repeatedly and finally, one night, we talked more realistically about the possibility of a threesome.
She had always been against it in the past but now I could see the wall coming down. Maybe if it was someone she didn’t see often. Maybe if it was someone attractive whose role in her life and in our friendships could be purely sexual. If we could make sure there was no emotional entanglement and that we could keep the bedroom in the bedroom and the rest of our friendship in the real world, maybe, just maybe, it would be okay. She admitted that if someone could be sexual with her (while with me present and involved, of course) but not reference or bring up that sexuality in the rest of their friendship with us, it would probably be worth pursuing.
In the coming weeks, we didn’t talk about it anymore and I planned to table it for a few months and then bring it up again after a few more bouts of particularly intense simulated threesomes. Sharayah surprised, me though, because about a month after our original conversation, the following happened.
I came home from work one day, surprised to find her already in the house. “Hey…you’re home early,” I said as I reached the top of the stairs in our apartment.
“I took a half day,” she said, smiling.
“Oh,” I replied. “What for?” Without answering, she sauntered over to me, placed her hands on my chest and slid down my body. Sharayah rarely initiated sex, she found it too intimidating, but this was close to her go-to move. She landed on her knees in front of me and unzipped my pants, immediately tugging them, and my boxer-briefs, to the floor. My cock was soft from the cold Wisconsin winter but after only a second or two of the visual stimulation, it was beginning to firm up. She leaned forward and, while making eye contact with me, licked the length of my cock and then took the head into her mouth, sucking gently. I moaned and leaned back against the half wall at the top of the stairs as she began to expertly blow my cock. Usually I was able to hold on for a long time and score thirty or more minutes of oral attention before moving on but I hadn’t masturbated that day at all and that, coupled with the sexiness of how forward she was and how talented she was brought me to the brink rather quickly.
“Easy, kid,” I told her, like I usually did, knowing she was still gun-shy about me finishing in her mouth. Usually when I said that she would slow down, or release me for a few minutes so that my nerves would calm down. This time, however, things were different and she buried my cock in her mouth, the head sliding into her throat. The wet warmness of it pushed me over the edge and soon I felt my body shuddering and releasing my cum down her throat. I breathed heavily and slowly came down from the orgasm as she wiped her mouth with the back of her hand and stood.
“Wow,” I said at last. “What brought that on?”
She smirked. “I know you’ve been really patient with me and exploring my sexual fantasies and helping me get over hangups and whatever. So I wanted to reward you a little bit before we move on to the next thing.”
I furrowed my brow a bit and pulled my clothes back on. “What’s the next thing?”
She smiled even more coyly. “Well you know how we’ve talked about threesomes and played around with the idea and stuff?”
“Yeah?” I asked expectantly, wondering where she was going with it. Was she planning on pushing toward actual double penetration with a full-size cock in her ass? Was she maybe thinking about how she might need to reciprocate the idea of a threesome and consider finding a way to simulate bringing another girl into our experience?
“Well I used to think that I would never want to actually involve another person in our sex life but I think the past six months with you and our toys has brought me past that. I really, really like having a second cock to play with while you fuck me.”
I nodded, pretty sure I was about to see a wall come down for her. Maybe she was ready to start discussing who we might want as a partner. “It has been fun.”
She nodded. “I’ve been talking to Garrett.”
“Oh yeah?” I smiled. Garrett was one of my closer friends and had been throughout my life. We had talked about our crushes and what we liked in women all throughout our childhood and adolescence and he and I had continued a dialogue about our sex lives even after I got married to Sharayah. She had always been a bit annoyed by his demeanor and occasional immaturity but had always been open and honest about the fact that he was one of my more attractive friends. Garrett was about the same height as I was, but thinner. He had dark hair and dark eyes and was something of the yang to my yin in Sharayah’s world.
“About what?” I coaxed.
“Sex stuff,” she admitted.
“You barely like talking to him about regular stuff. What brought that on?”
She shuffled her feet a bit. “I think I wanna try having a threesome in real life. With a second man involved. The toys are great but a real cock is still worlds better than even the most realistic dildo.”
“And you started talking to Garrett about that?” I clarified.
“Sort of.”
I nodded. “So you were trying to feel out the situation and see if he was interested in maybe being in a threesome with us?”
She shrugged. “Not exactly. I started with small talk and then asked him if he thought I was attractive and kinda baited him into flirting with me and then when I was sure he would be interested, at least in theory, I asked him if he’d ever thought about a threesome.”
“And what’d he say?” I asked, curiosity getting the better of me now.
She smiled. “He said he’d thought about threesomes, he’d thought about what it would be like to fuck me and he even said that he’d considered you before as one of his potential threesome partners if he were ever to do a girl, guy, guy threesome.”
I nodded again and smiled a bit. “Oh, cool. I’m glad to know he was open about all that with you.”
“Mhm,” she said, biting her lower lip. “So he should be on his way over here by now.”
I paused. “Wait, on his way over here for…”
“For the threesome,” she said, matter-of-factly. My eyes widened just a bit. My conservative wife had just attacked me with oral sex the second I walked in the door, which she had almost never done, swallowed, which she had never done, and was now admitting to talking about sex with a male friend of mine, propositioning him for a threesome, and then setting a time and date and inviting him to it, something I never thought she would have ever done. I had been sure that I would be the one to have to initiate the threesome and recruit the other player. And now, here I was, twenty minutes or less from what she intended to be probably only the first threesome experience of our marriage.
“Wow. You just took the initiative with that, huh?” I asked.
“Are you mad?”
“No.”
“Are you sure?”
“Yes.”
“Do you think it’s a good idea?” she asked, a little of her trademark insecurity showing.
“I do,” I said. “I think it’s going to be hot. Are you sure you’re ready for two men?”
“Mhm,” she said with a smile. “I mean, I’m not one hundred percent but I don’t think anyone ever could be. I figured I needed to just embrace it and give it a try. If I wait until I’m completely convinced it’ll be great I’ll probably just never get around to it.”
I looked to the front door. “And he’s on his way now?”
“Yes, he texted me about ten minutes ago.”
“Wow,” I said, smiling, pleasantly surprised. “Any idea what you want to happen?”
“It’s all up to you boys,” she said, moving and sitting on the couch. She crossed her legs. “I’m up for whatever the two of you think you wanna do to me.” My mind reeled at the possibilities. Here was my wife of two years suddenly showing so much sexual open-mindedness that it was just…almost unthinkable. She had invited my friend over and into our bed and was giving me tabula rasa to do whatever Garrett and I thought was best.
The next fifteen minutes passed by slowly but sure enough, Garrett came up the walk in front of our apartment complex and, after a brief knock on the door, opened it, said hi, and started up the stairs. At the top he kicked off his shoes and the three of us briefly stood and looked awkwardly at one another. Sharayah shrugged her shoulders with her hands in her pockets, inadvertently pushing her breasts together and showing deep cleavage in the low-cut top she was wearing. Both Garrett and I stared. Finally, he broke the tension.
“So, uh…so hey,” he said, awkwardly unsure how to start a conversation about a threesome.
“Hi,” I said simply.
“She just told you?” he asked.
“Yeah.”
“You’re okay with it?”
“Yeah. Looking forward to it, actually. You?”
“Same. It’s one of my bigger fantasies.”
Sharayah smiled.
“So, uh,” Garrett asked, deciding to just go for it. “How do we start?”
Sharayah bit her lower lip, reached out, and put a hand on each of our bulges, her fingers deftly curling about the outlines of our cocks as she gave a little tug. “Follow me, boys.” She led us to the bedroom and then released us and turned to face us again. With a look to Garrett she stepped up to me, stepped up on her tiptoes and kissed me, sliding her tongue into my mouth. I reached around her and grabbed her ass, pulling her to me and pressing her huge breasts against my chest as we made out. After half a minute she broke the kiss and lowered herself back down, then stepped over to Garrett and repeated what she had done with me. He looked at me for a moment as if to check if I was really okay with it, and then likewise grabbed her by the small of her back and pulled her against himself as he kissed her back, the two of them sliding their tongues into one another’s mouths.
I watched as my wife kissed the first man other than myself since our wedding. Narrow-minded jealous parts of myself screamed that I should be stopping this and hitting him and mad at her but I squelched them. She wanted this, I wanted this, and he wanted this. It was petty and close-minded to think that I should object. After thirty seconds of kissing Garrett, she broke the kiss and he released her, his hand trailing up her back and along her side, brushing against the side of her breast as he did so. She blushed a little, then stepped back. She took a deep breath and I saw that, on some level, she was nervous to do this. A part of her was hesitating and not sure if she wanted to go through with it. She looked at me for reassurance or for encouragement to stop and I simply raised my eyebrows at her seductively. She smiled and it seemed like all she needed to push her over the edge. She grabbed the hem of her top and pulled it up, taking it off over her head and revealing her flat, toned stomach and her lacy black bra, the only thing keeping Garrett from being the only other man to ever see her topless.
“Mmm,” he said. She giggled lightly and then reached behind herself, arching her back lightly as she began to fiddle with the clasp on her bra, knowing she was about to cross the point of no return. Here she was, in one minute, a shy, sexually conservative wife who had only ever been with one man, and, in another minute, she would be a sexually adventurous wife who had revealed herself to two men at once. She paused at the gravitas of it and then unclasped her bra, pulling it down her arms and tossing it aside. One look at Garrett’s face confirmed for me that he was absolutely turned on by her body. Her breasts were huge and without the sag that usually accompanied busty women. Her nipples were just smaller than average, upturned, and slightly hard from the sexuality of the moment. He looked her up and down a few times, his eyes roving over her body. I could tell he was dying to touch her and I knew he was a good enough friend that I would have to break the ice on that.