My first failed attempt to have a male male female threesome.
The year was 2006 and I had just recently graduated high school and moved into my first apartment with my girlfriend at the time (also bisexual) and two other roommates. Our first night in the apartment we happened to be attending a local music show. We didn’t have our mattresses or anything moved in yet, however we’d still made plans to meet up with one of my ex-boyfriends and take him back to our place afterwards. My girlfriend, Jenny, really wanted me to have my cock inside her while having a cock inside me, and I didn’t mind the idea either. Having something thrust in and out of my ass has always made me come faster and harder.
At the show, the last act had taken the stage and it became clear that my ex boyfriend wasn’t going to show up nor was he answering his phone. However, Jenny wasn’t going to give up that easily. Among our many friends at the venue, we knew one was bisexual and she knew him and I had almost messed around a couple of times before. By trading pictures online I knew he had a long and slim dick and a nice slender body even though his face wasn’t great looking. He had been in a long term, semi-long distance relationship with a girl for many years, but Jenny had no problem asking Richard if he wanted to come back to our apartment with us to drink some wine and “see what happened”.
I wasn’t surprised he agreed and as soon as the show was done we were off. We didn’t waste any time getting to the bedroom where he and I took our shirts off while Jenny poured some glasses of wine. Sitting with our backs rested against the wall, we made some idol chitchat, flirted and quickly drank our first few glasses. After her first glass Jenny stood and removed her shirt and then skirt. She poured herself another glass then sat back down between the two of us in her bra and thong. Jenny was thin but curvy and I could tell Richard was enjoying his view. She started to tease us that it was unfair for her to be only in her underwear while we still both had our pants on. I got her drift, undid my pants and removed them with haste. Then we both were looking at Richard, waiting for him to do the same. He smiled and chugged what was left in his glass before standing up to strip his pants off. He started to move awkwardly as he made his way to the other side of the room and brought back the mostly empty wine bottle and quickly sat back down, I think hoping that the fact his penis was semi-erect in his boxers wasn’t too noticeable. It was.
Resting his back against the wall again, Richard started to pour himself another glass. Jenny put her hand softly on his crotch and began to lightly rub his cock through his thin underwear. The bulge become longer and began to slowly stand erect, all the while become more and more defined within his boxers. She stopped for a moment to remove her bra but quickly returned to petting Richard’s dick. Without stopping she turned her head to look at me and smiled. I smiled back and she began using her left hand to give me the same treatment Richard was getting even though after watch her pet him, my tool didn’t need much more help getting hard.
When she could tell we were both nice and rigid, she repositioned herself to be lying on her stomach directly in front of Richard. She made and then kept eye contact with me the entire time she slid off his boxers to reveal his hard, big cock. She didn’t stop looking into my eyes as she began to wrap her mouth around his 9inch prick. She moved her head slowly back and forth while he let out a long sigh and ran his fingers through her blonde hair.
I moved over a couple feet to where they were and joined Jenny on my stomach on the floor. She gripped onto the base of his warm member and together we licked his shaft from top to bottom. She began to blow him again but this time after every few strokes of her mouth she would remove the tool, stilling holding onto it’s base, and point it at me indicating it was my turn to suck on it. We did this for a few moments taking turns with his long cock in our mouths every 10-15 seconds.
While Jenny was taking her turn again I noticed her right had down the front of her thong obviously rubbing her clit. I scooted myself backwards until I was behind her and had her change positions from lying down to on her knees with her head still moving up and down in Richards lap and her ass and wet pussy up in the air for me to play with. I tore off her thong and began to shove my index and middle fingers into her sopping slit. I placed my face up between her legs and licked and sucked her clit while I continued to finger fuck her.
Jenny started to moan and groan and I could tell by the tensioning up of her thighs that she was going to come soon. She pop Richard's piece out of her mouth and began to stroke his dick with long up and down strokes, her spit I’m sure was making excellent lube for her hand job. She got louder and louder and finally let out a little scream as her body trembled. When Jenny finished, she looked back at me, panting. Between her deep breaths all she could say was, “god damn.”
She moved over to where we’d set up a fully opened sleeping bag and laid on her back, with her legs spread wide open showing both Richard and I the pink of her glistening pussy. Him and I both joined her on the sleeping bag, again with one of us on each side of her. I started to suck her neck and caress her B cup breasts as Richard kissed her on the mouth and moved his hand between her thighs and started rubbing her clit. After a few moments I let go of Jen’s tit and grabbed a hold of Richard’s penis and was a little surprised it wasn’t as hard as it had been earlier. As I worked his entire shaft with my hand he regained his firmness and then moved his hand from Jenny’s clit to my dick, which he slowly but steadily stroked.
We could both tell Jen loved to watch us jerk each others wood. She was soon rubbing her own clit again and squeezing her tits while we had our arms crossed over her playing with one another. Her eyes rolled into the back of her head momentarily and it caused both Richard and I to let out a little laugh. Jen heard us laughing and when she opened her eyes again she gave us both a smile then looked into my eyes and told me,
“I’m ready for you to fuck me.” After a very brief pause she added, “Hard.” With that being said Richard moved back slightly and I climbed on top of Jen. I threw her legs over my shoulders and slid my cock into her soft and wet cunt. I started slowly with the motion of my hips, moving myself in and out of her gently, making her wait for the hard screw. As I fucked her I grabbed onto Richards manhood again and began to tug on him just as softly as I was penetrating Jen. I asked Richard to lean over a little and hand me the lube Jen had purchased earlier in anticipation for my ex. Once it was in my hands I poured a generous amount onto the tip of his tool and let it run down his shaft. I made sure to grease up his entire dick then had Richard position himself behind me.
I kept still inside of Jenny’s twat so that Richard could have easier access to my asshole. It didn’t take long before I felt his long skinny cock slide up inside me deeper than the few others I’d had in the past. The fact that he had a good amount of length was really rather convenient, someone with a dick not as long might have had to position himself closer to me and may have fallen out of my crack while I thrust my hips back onto him and then forward into her. The soft sex was over and it was time for some hardcore fucking. Having enough space to cram my 7inches into Jen while keeping his slippery member in my hole was a great feeling.
However, after just a couple of minutes I could feel Richard loosing his stiffness. I knew he hadn’t come inside me and started to wonder if he maybe drank too much too fast. I kept on pounding Jen’s cunt nice and hard and I reached behind me and began to message Richards sack. Sadly, it didn’t seem to help. Before long he wasn’t even hard enough to push his dick in and out of my ass.
He pulled himself out of me and moved to my right. Without stopping our fuck action, Jen and I asked him what was wrong. He said he was just having some issues and that it was fairly normal for something like this to happen to him. I didn’t know it at the time but this would become a reoccurring trend in my three-way sex life with other men. I started to slow down the motion of my hips trying to give Richard some time to regain his wood. It finally seemed he was back to standing at attention so Jen told him to come back over and join us.
“In a minute.” Rich said.
I returned to fucking her slowly because it felt too good to stop all together and we waited a few more moments while we watched Richard play with himself some more. A few moments later we asked him again to join us and again we got the same response. After about the third or fourth time we were told to "hold on just a minute" I decided to go back to really plowing Jenny’s twat. About 10-15minutes passed and Rich still hadn’t come back to finish humping me and Jen and I noticed he was having trouble staying stiff again.
I began to get a little frustrated and confused so I abruptly pulled my dick out of Jen and sat on the opposite side of her facing Richard. Though Jen and I really wanted to finish in the position in which the three of us had started, I decided any threesome action was better than none so I asked Richard if he’d rather fuck Jenny than me. Jen gave me a quick glace as if to ask if I was really okay with him screwing her, which I was. I knew that even though I never had any problem getting Jen to come multiple times that the extra couple of inches Richard had to his piece would be a new and different feeling than the cock she’d been having pump her pussy for the last few months. I honestly thought it’d be fun to see the face and hear the noises she was going to make when he slid the entire length of his manhood into her and reached places I couldn’t.
He declined. I explained to him that I was totally cool with it and that I would get a kick out of having Jen blow me while he pounded her. Then Jen explained to him that she hadn’t had a cock that long in a while and that she was more than fine with it as well. Still he declined. He said instead that he’d rather watch me finish fucking Jen and for me to blow my hot load on her face and chest. So I climbed back onto Jen and put her legs back on my shoulders. I felt bad for raising her hopes about receiving a long dick so I made sure I fucked her hard and pushed my dick in as deep as I could get it, and pulled it out to the point where it almost wasn’t in her anymore just to stuff it back in. At first Richard kept playing with is limp dick, but after about the first 10 minutes or so he stopped altogether and just sat back with his glass of wine and watched.
“I know you can fuck her harder than that.” I heard him say. I increased my speed in and out of Jen and then heard him say, “She really likes it like that, I can tell.” I asked him one last time if he was positive he didn’t want a piece of Jenny’s ass and again he declined. He replied, “Just fuck her for the both of us.” So I did.
I flipped Jen over and put her back in the face down, ass up position she was in early when I was fingering her. I pounded Jenny’s slit from behind for a while and occasionally we would get a suggestion from Richard. Things like “you should slap her ass” or “maybe pull her hair” before long became orders being barked at us from Rich. “Fuck her. Fuck her tight pussy. Make her melt. Make her fucking come” I fulfilled his wishes for about 45min-1hr. and about the fourth or fifth time Jen came on my dick I could feel the pressure start to build up at the base of my cock. I didn’t slow my thrusts at all. I was ready to come. I took a look over at Rich and his eyes were focused on my penis sliding in and out of Jenny. I then glanced down myself and that’s what closed the deal. Seeing my now soaking wet shaft glide between her pussy lips in synch with the pleasure I was feeling I knew I was about to blow and having someone watch made me want to pop my load that much harder.
I pulled my wood from her twat and rolled her back over onto her back. I stayed on my knees and moved myself so I was looming over her with my throbbing dick in her face. I made eye contact with Richard and kept it even when I could feel Jen’s tongue flicking from side to side on the tip of my pole. I was still watching his eyes as I ferociously stroked my cock and ejaculated a thick and hard stream of sperm across Jenny’s face and I saw them shift from my face to my come shot once it started. I pumped out the rest of my load and let the last few drops drip onto Jen’s tits. She swallowed what landed in her mouth and we both took a second to catch our breath. After cleaning up my mess the three of us climbed into the sleeping bag to go to sleep.
The next day after we dropped Richard back at his house he began texting us apologizing for the night before. Apparently he become unexplainably nervous and wasn’t able to perform. Jen and I were a bit disappointed that things didn’t go as planned and that we hadn’t got to fully fulfill our fantasy but we did have a good amount of fun.