A grad school classmate of mine started coming to the gym with me last year. He’s a bit shorter, less in shape, Asian. The first time we went together, we worked out, then swam, then as we were showering afterwards, I noticed he kept his swimsuit on (although I took mine off). I’m pretty well hung – 8″ when hard, and about 6″ soft – and he was not being very discrete about staring at mine while we were showering.
We became better friends, and I ended up meeting his girlfriend (a white girl, although she’s very petite – smaller stature than him, actually) and hanging out with them a few times.
One night him and I were showering after swimming together, and he started asking why I didn’t have a girlfriend. I told him the truth – that I was just having a hard time finding someone – but he said something like, “Yeah, they probably run away scared after you show them that monster”, pointing to my cock. I said, “Well, you’ve got a girlfriend – I’m guessing whatever you’re covering up over there isn’t exactly scaring the girls away.” That was meaner than I meant – I was just trying to tease him – but he blushed and said, “I’m not scared to take my swimsuit off…” (although it seemed like he was), and pulled his swim trunks down.
It was obvious he was nervous but a little turned on – he really didn’t have much – maybe 2-3″ – but it was semi-hard, sticking straight out. I gave it a look and jokingly said, “It’s ok – your girlfriend is tiny, too” in a teasing way.
“Too much is no better.” he said, ” No way yours would even fit inside her”.
“I don’t know,” I said. “I’ve fucked girls not much bigger than Sara”
As we talked, I noticed he was turning inwards to hide his growing stiffness from the rest of the (empty) locker room.
“I’m the only guy she’s ever had sex with. You really think you could fit all that inside her?” he said, much more seriously, now.
“Probably. If she’s never had one bigger than yours, mine would definitely stretch her. It would be a struggle to get it all inside of her.”
The imagery must have been too much for him, as he closed his eyes and I saw his stiff cock spasm, as he turned to try to hide it from me.
I pretended I didn’t notice and finished up showering. We left without saying anything about it, but the next day, he texted me and asked if I wanted to come over and hang out with him and Sara. I figured I knew where this was heading, so quickly agreed.
At their place the next day, we had a few drinks, and Sara was much closer and “touchier” with me than usual. At one point, she reached across me for something and “accidentally” fell with her hand landing right on my junk. “Oh my gosh! Sorry!” she said, but she left her hand in place a bit longer than necessary.
“It’s ok” I said. “I’m not shy,” I joked.
“Yeah, Eric told me you aren’t very shy,” she said. “He, on the other hand, is very shy, aren’t you, honey?”
Eric blushed, but I saw this as an opportunity to push things a little further. “I don’t think he’s that shy,” I said. “I mean, if he were really shy, he’d probably die of embarrassment if he had to, say, I don’t know…stand naked in front of us”
“He definitely doesn’t have the guts to do that!” Sara laughed.
Eric was flustered, now, but seemed determined not to be too emasculated in front of his girlfriend. “I’m not too shy!” He said. “I’ll strip for you perverts if you want!”
“Go for it!” I said. I think he thought we’d back down, but Sara and I were sitting in anticipation.
“Fine.” He said with some resignation. He pulled his shirt off, then quickly dropped the basketball shorts he was wearing, leaving him standing naked in front of us, with his cock half-hard between his legs, and his little balls pulled up tight.
Sara and I looked at him for a minute, then she said to me, “Do you and Eric look similar with your clothes off?”
“Actually,” I said, “I think YOU and Eric probably look more similar with your clothes off than he and I look”
She giggles at this thought. “Well, let’s see”, she says, and pulls her T-shirt off. She reaches behind her back, and unclasps her bra, letting it fall down and expose her little breasts. She stands up, and pushes her leggings off, leaving her standing next to Eric, both of them naked.
She has one hand covering herself, but reaches her other hand over to cover Eric’s package and says, “You’re right – looks about the same when you can’t see what little is under my hand”. I don’t think Eric totally appreciated the teasing, and said something like, “Now who’s being the shy one?” as he grabbed both her arms, uncovering her, and letting me see all of her naked body.
She giggled and tried to fight free, but he was holding her arms behind her back.
I was getting hard, and the bulge in my pants was obvious. “Well, let’s see how you and Eric compare” Sara said.
I figured, “Why not?”, and stood. I took off my shirt, then unbuttoned my pants and pulled them off. As I lowered my boxers, Sara and Eric’s eyes both got big and they almost simultaneously said, “Holy shit!” as they saw my hard cock spring free.
The lighthearted mood quickly changed, and they were both just speechlessly staring.
Finally, Sara said, “That thing would never fit in me. No way.”
“At least try…” Eric said (obviously they had planned this before I had arrived…)
I’m standing there with my cock hard, while Sara is facing me, and Eric is behind her, still holding her arms behind her back. He steps forward, pushing her towards me, filling the distance that had been between us. My cock slid between her legs, grazing along the front of her slit, where I felt how wet she already was. She gasped at the contact and slightly gyrated her hips to rub against me.
I started slipping it back-and-forth along her slit, but she was obviously really turned on, already.
“It’s so big!” she said.
“Well, what are you waiting for?” Eric asked me.
I felt a little weird, thinking of trying to penetrate her from the front, while her boyfriend held her arms behind her, but she just looked at me with wide eyes and didn’t say anything. So I squatted down a few inches, grabbed my cock, and started running it along the length of her slit until I felt the head slip into the tight entrance to her vagina.
I slowly started pressing into her, and she gasped as the head of my cock worked its way inside. I pulled back a little, then pushed forwards until an inch or so was inside her.
She was just taking these shallow little breaths, and seemed to be fixated on the feelings between her legs, so I just kept going. Pull out a little ways, push in a little further. When I had about 2″ in, she said, “Uugh, I feel like I’m already being stretched like I haven’t ever felt, before…” as she looked over her shoulder to see Eric’s reaction.
I kept going further into her, but the going was so slow. The desire to feel myself actually buried inside her was too great, and I put my hands on her hips and took a more forceful thrust. This time, several inches went in at once, and she shrieked. A few more thrusts, and I had it almost all the way inside. I couldn’t quite get all the length buried, but I was most of the way inside her. I started fucking her in slow, deep strokes, and she was trembling from the sensations. I looked down, and her slit was stretched around my cock in a tight grip that left it red and distorted. “Oh my god…oh my god…” she kept saying. “He’s so big. He’s so deep in me.”
The sloppiness between our legs was ridiculous. She was so wet – it was getting all over me, all over the insides of her thighs, and all over Eric’s cock, which was pushed between her thighs from behind. As I started fucking her, he moved in closer, and I could feel my balls slap against the head of his cock, resting between her thighs, every time I bottomed out in her.
“This is so intense, Eric”, she said. “This is so different than when you fuck me”.
Sara’s comment must have triggered something, because Eric got a determined look in his eye, and said, “Oh yeah? Well, let’s see how intense this is…”
At first, I didn’t understand what was going on, but he reached down, positioned his cock, then Sara started shrieking. I was still in her vagina, but his cock wasn’t between her thighs any more – I realized he had pushed himself up her ass. “Ahhhh!” she yelled, “You know I’ve never done that before!”. I could feel his cock thrusting in her from where I was holding still in her pussy. “You want me to take it out?” he asks. A long pause – then a, “No…”. The thought that he had just taken her ass (without her expecting it) was too much, and I started fucking her from the front, again. In a few strokes, I could feel myself about to orgasm. “I’m going to fill your pussy with cum, Sara” I said. She started convulsing in her own orgasm as I felt myself spasm inside her. As I pulled my cock out of her, my cum trickled out of her, dribbling down the inside of her thighs, onto Eric’s balls, as was thrusting away in her ass.
“How’s it feel to have my cum on your package, Eric?” I said, which was apparently enough to send him over the edge, too, as he grabbed Sara’s hips, pulled himself deep into her ass and came.
As he pulled out of her, he let go of her arms, and we all fell to the floor. Sara’s legs splayed apart, and put her pussy on display for Eric and I. It was red, swollen, and stretched. Cum was still dribbling out and tracking down her legs. I looked over at Eric’s deflating cock as he looked over at mine, then over to his girlfriend’s pussy. “Hope she gets used to the idea of you fucking her ass,” I said.
Source: reddit.com/r/gonewildstories/comments/g2emp9/mmf_cuck_giving_my_friends_girlfriend_her_first
90% sure I’ve read this story from a different account.