My Swimteam Buddy and my Girlfriend

by Andrew J

Check out my blog at

If you are not 18 or older, please leave immediately. Do not continue reading.

Disclaimers: This story is pure fiction. Any resemblance to real life events or people is co-incidental and unintended.

Feedback, comments, thoughts, criticism are all welcome. It’s always a pleasure to hear from readers. Leave a comment, or read what others had to say here, or email me at :

Rich was my best buddy. We’d been best of friends ever since were on the swim team together at UCSD in our college days, 8 years ago. Every year, Rich invited several of his old buddies (and their girlfriends/wives) to San Diego to spend a long weekend with him at his beach house. I always looked forward to this get-together. Most years, given I was usually single, I went alone. This year, however, was different.

Cindy and I had been going out for six months. I met her at my gym in LA, where she worked as an aerobics and spinning instructor. Cindy was 25 years old, drop-dead gorgeous, and had the body of a professional model. I was looking forward to her meeting my old college buddies, especially Rich, and was ecstatic when she agreed to go with me.

My buddy Rich was handsome, wealthy, and extremely charming. He was the kind of guy that every guy wanted to be friends with, and that every woman wanted to date. He had a way with the ladies, and pretty much got any woman he wanted, no matter when or where.

So I wasn’t surprised in the least when the two of them instantly clicked. Rich was immediately taken by Cindy’s innocent, girlish demeanor, and Cindy was equally taken by Rich’s tall, slender, swimmer’s physique.

It had been a long day, and Cindy and I were both relaxing in our guest bedroom at Rich’s house. Cindy was wearing a sexy, sheer pink negligee. It was very cut low... almost down to her breasts, and was very short, barely covering her crotch. Underneath she was wearing a pair of matching silk panties. I was wearing my trusty white boxers. I always wore white boxers... I loved the way they showed off my tan and my immaculately hairless swimmer’s body.

We were stretched out, chatting about nothing in particular when we heard a knock on our bedroom door.

“Brian? Cindy?” It was Rich’s voice. Not waiting for an answer, he opened the door and came into the bedroom. "Just want to make sure guys are doing OK here!"

"Hi Rich!" Cindy's eyes lit up as soon as she saw him.

Rich was wearing nothing but a pair of white boxers, just like mine. He held a bottle of champagne and 3 glasses.

"I feel like celebrating our all being together! Care to join me?" Rich poured us 3 glasses of champagne.

“Oh, I’d love to!” Cindy said, instantly perking up.

"Thanks for having us, Rich!" I said, as we toasted.

"And it is such a pleasure to meet Cindy," Rich said, sitting down on the bed. I had to scoot over to make room for him.

"Thanks, Rich. Brian's told me so much about you!" Cindy took another sip of champagne, and, under his gaze, adjusted her negligee. Her long, shapely, smooth legs were in full view, looking bare and delicious.

"Wow, Bri. I didn't know you had such good taste in women!"

This made Cindy giggle. The two of them looked each other over, slowly and carefully. Their bodies were on display to maximum advantage.

Rich slid up on the bed, causing his boxers to ride down slightly. His six pack abs and groin area were smooth, and bronze against the whiteness of his boxers. The waistband of his boxers was well below where his pubic hair should have started, revealing that, just as me, he had kept up the old swim team habit of staying completely shaved.

"So you both having a good time in San Diego?"

"Uh huh, and it just keeps getting better and better," Cindy said coyly. “It's so beautiful and sunny and warm! And you men are all in such great shape."

The two of them continued to flirt with each other as I looked on. I was increasingly beginning to feel like the third wheel, lying in between Cindy, who lay on my left side, and Rich, who was sitting at the foot of the bed to my right.

"So how do you stay looking so hot, Cindy?" Rich asked, his eyes twinkling as he refilled our glasses.

"Well, I try to stay active, and teach fitness classes back in LA," Cindy said. "Keeps my legs in shape and firm." she said. Seductively, she lifted her legs one at a time and slowly caressed them from her knees up to her inner thighs.

"Mmh... I can see that," Rich said, his voice getting huskier.

Like I said earlier, Rich usually got every girl he wanted. So, naturally I was getting uncomfortable as I watched him flirt with Cindy. I wasn’t too surprised though. He flirted with all the women I ever dated, and I knew for a fact that he’s slept with every single one of my girlfriends, without exception, ever since we were freshmen. There were only two girls that I went out with that Rich hadn’t had sex with. Those were the two relationships that didn’t last very long. They seemed to end when I found out Rich didn’t like them.

It was, admittedly, a funny relationship Rich and I had. He was the alpha male, and I'd long ago given up trying to dispute that. Over time I’d even grown comfortable with it, and had come rely on his judgement in women.

Still, every time he flirted with one of my girlfriends it made me terribly uncomfortable. I hated it, in fact.

"So, it's been a long day. Cindy and I want to turn in..." I said weakly, hoping Rich would go away.

"No we don't," Cindy said, looking at me with a mixture of annoyance and surprise.

"It's OK, if you're tired I can go," Rich motioned to get up.

"No, no. Stay. Please. We'd love for you to stay," Cindy said, practically pleading.

"You sure, baby?" Rich sat back down, smiling that prize-winning guaranteed-to-get-laid smile.

“Yes!" Cindy exclaimed, re-adjusting her negligee, which kept riding up.

"I have to take a piss. I’ll be back,” I said, a little flush. I was irritated with both of them, at the same time vaguely excited. After taking a piss I went downstairs to see what everybody else was up to. The party was still going on, and a few of my buddies and their girlfriends were hanging out and drinking. They invited me to hang with them, but I declined, saying I had to get back to Cindy.

"Rich upstairs with you guys?" Dave asked, pulling me aside.

"Yeah," I said, nodding. “When’s Steph getting here?”

“She’s flying in tomorrow morning.”

Dave was another UCSD buddy. He was probably my second best friend after Rich.
He and his girlfriend Stephanie had been going out since college, and lived up in San Francisco now. I’m pretty sure Rich had gotten it on with Stephanie, and I wouldn’t be surprised if they still occasionally did.

Dave and I would quietly commiserate whenever Rich hit on, or inevitably, had sex with one of our girlfriends. We never discussed anything out loud, but knew that it happened. We also knew that we both found the whole situation vaguely erotic. This was probably why he and I were such good pals. We were both self-loathing and mildly perverted.

“Well, I’ll see you tomorrow Dave,” I said, heading upstairs.

“Oh, Bri -” Dave continued, looking upstairs, and then at me knowingly, “If you need a place to crash tonight, you’re welcome to stay in my room.”

“Thanks, bro!” I said.

By the time I returned to our bedroom, Rich had taken my spot on the bed. His hands were clasped behind his head. Cindy was on her side, her face almost touching his elbow. They shared a pillow. Her long blond hair fell in wisps, some of which lay on Rich's bulging left biceps.

They were both laughing and giggling as he told her stories about his glorious swim team days. I refilled our glasses with champagne, and sat at the end of the bed.

"And you, baby? Tell me about your work. I bet you're a really good teacher."

"I’m OK, I think. I try really hard!" Cindy said earnestly.

"Naw. I bet you're the best there is. I'd let you teach me!" Rich said. He lightly touched her head and stroked her hair. "Every day, if you wanted, baby."

Cindy giggled, and blushed.

"You wouldn't need my help, Rich. Not with a gorgeous body like yours." Using her long fingernails, she lightly traced a line from his left shoulder down to his six-pack.

Rich shuddered in pleasure.

I looked down to see a large tent in my buddy's boxers. He had a huge cock. I'd seen it several times before, both flaccid and erect. It was bigger than any guy's I'd ever seen with the exception cocks I’ve seen on porn sites or magazines.

"Let's see what your tummy feels like, babe," Rich said, turning inwards. He slowly caressed Cindy's stomach, over the silk of her negligee, and making long, sensuous lines across her abdomen. He stopped exactly where the fabric of her negligee ended, which was less than an inch below her pelvis.

“Ooohhh…” Cindy moaned. Her eyes were half closed.

"Hey, hey, what's this, baby?" Rich had stopped at her belly button.

"Oh, that's my piercing,” Cindy said excitedly. "You want to see it?"

That was too much. I'd had enough. "OK, guys. Rich, I think you need to go to bed. We're turning in now." I said, trying to sound as angry and determined as possible.

"Relax, Bri. I'm just getting to know your girlfriend here. Nothing wrong with that, right?"

"Yeah, relax, Brian. We're just chilling," Cindy rolled her eyes at me.

I couldn't argue with the two of them. Done with my protesting, atleast for the moment, I poured myself some more champagne and sat back.

"So you wanna see my piercing?" Cindy asked again.

"I'd love to, baby," Rich said. Rich's cock was fully erect, and pointed straight out, poking out above his waistband of his boxers. It didn’t throb or bounce. It just pointed. Straight and thick, and hard as a baseball bat.

She pulled her negligee up to her breasts, revealing the silky smooth skin of her mid-section, and the pink diamond stud in her navel. Cindy had the most beautiful stomach of any woman I'd known. Her whole body was a single, milky complexion, with no imperfections. The lace of her low, almost non-existent panties left little to the imagination. I stared transfixed, as my best buddy’s hand touched my girlfriend’s stomach.

"Mmm... baby. It's beautiful," Rich slowly tugged on and twirled the piercing in his fingers. His tanned, big fingers looked undescribably sexy against her midriff and tiny waist. “It makes you so sexy. Like a really sexy, beautiful woman!”

Cindy moaned in response to Rich’s touch. She then arched her mid-section upwards invitingly.

Rich slowly started caressing the rest of her stomach. Cindy kept her body, including her pussy, completely hairless. This was one of the few things I sought as a requirement in the women I dated. I didn't have any body hair and didn't want to be with anyone who did.

Rich's hand slowly traced the thin lace waist of her panties, but not going any further. My girlfriend's nipples looked erect, and made two small tents under her gown which was bunched up over her breasts. I desperately wanted to reach out and touch them. By now I was completely hard, and a small wet spot had formed on my boxers.

"You are so hot, baby. My buddy Bri is a lucky man," he said. His head hovered over hers, like he was about to kiss her.

"Brian has such nice handsome, strong men like you as friends," Cindy said, reaching up and kissing him.

I saw Rich's tongue enter Cindy's mouth and they slowly french-kissed. They continued kissing for several minutes, until Rich broke away.

"You wanna see my tattoo, baby?"

"Ooh, you have a tattoo??? Yes, please. I love tattoos!" Cindy cried enthusiastically.

Rich pulled away and slid his boxers down a bit. His erect cock, which was already out, was now completely exposed, as were his large balls.

"Ohh!" Cindy gasped.

"You haven't even seen it yet, baby!" Rich said.

Cindy blushed, embarrassed. "I know, it's just -"

"What, baby? Tell me what you're thinking," Rich said, as he slipped his boxers completely off and proudly jutted his pelvis out towards her.

"It's just... it's so big!" she said softly, giggling," I've never seen one that big!" Cindy was staring at my buddy’s cock. “Ever. It’s the biggest I’ve seen in my life!”

Ouch. That stung. My face turned crimson as I listened to my girlfriend gush over my best buddy's cock.

Rich just nodded and smiled proudly. He lay back, and his cock stood out and upwards at full-high mast.

"You like that, baby?"

"Uh huh...." Cindy said, shyly looking away. “It looks so manly, and strong…”

"Here's my tattoo, baby." Rich spread his thighs a bit and lifted his right leg, revealing a small tattoo of a shark.

"Oohh! A fish!" Cindy shrieked delightedly. "I love it! Can I - "

"You wanna touch it, baby?"

"Yes, oh please!"

Rich lifted his leg, causing him to turn inwards towards Cindy. His legs were spread and his cockhead was inches away from her pussy. Rich guided her hand to his inner thigh, and she shrieked delightedly as her fingers made contact with the tattoo. He held her hand there with his, and they kissed again. Cindy then pried her hand loose and, using her fingernails, traced slow circles around his tattoo and all over his sensitive, inner thighs.

Precum glistened in a long, drippy trail from the head of my buddy's cockhead down onto his stomach and the area between them.

By this time Cindy was creaming too. Her panties looked drenched with her juices.

"Baby, baby, you're getting wet." Rich said, looking down "Your panties are all wet!"

"They are? Ooh, you're right." she said.

"Let's take them off. We don't want you catching a cold or anything."

Then, using his finger hooked under the lace waist band, he pulled Cindy’s panties off. Once freed, Cindy spread her legs wide.

This was going a bit too far. I really, really needed this to stop. With all the courage and anger I could muster, I said, "Ok, can we stop now? Please?"

"Bri, c'mon. It’s all good. Like I said, I’m just getting to know this gorgeous lady of yours." Then he looked back at Cindy with that winning look of his.

Cindy looked at me, thoroughly annoyed. "Brian, if you're tired why don’t you go somewhere else? I want to hang out with Rich some more."

I sat back, feeling humiliated, dominated, and horny as hell.

The two of them continued kissing and touching each other for a few minutes.

“Baby, you’re so wet!”

“Oh I’m sorry. Am I making a mess on the sheets?” Cindy asked innocently.

“No, no, no, not at all, babe! Wet’s what it’s all about, babe,” Rich said. “Here, why don’t you just get on top of me like this,” He gently lifted her on top of him, “So now my baby can get as wet as she wants and it won’t get on the sheets.”

Cindy now lay squarely on top of my buddy. I had a full view up their naked legs, to where there crotches were meshed together, and her curvy, feminine hips lay straight above Rich’s narrow, masculine hips. I watched Rich’s big hands move over my girlfriends back, and freely roam over her ass and the back of her thighs. His big balls, tight in their sac up against his body, were slowly being coated by Cindy’s love juices as she rocked and bucked her hips in a natural, involuntary rhythm.

“Mmm… that’s right, baby, get as wet as you want. Let it all flow, baby. Don’t hold back. It’s all about you, baby.”

Man, Rich’s husky voice was making even me horny.

“Uh... mmm…” Cindy cried as her pussy lips slowly rode up and down Rich’s erect cock. He hadn’t penetrated her but was aligned perfectly to do so. She was oozing all over his pubic area. Had he had any hair, it would have all been matted down by now. Instead, it generously lubricated their smooth skin and the motion between them, making their rocking and swaying all the more sensuous.

“Ohh, baby!” Rich suddenly shuddered. “Yeah, that’s it! Your navel bling is right up against my cock. Can you feel it?”

Cindy’s eyes widened. “Ohh, yes! Yes!” she said, suddenly stopping her rocking.

“Why did you stop, baby?”

“It’s just that – you’re so big I’m kind of…”

“Kind of what, baby?”

“I’m kind of scared,” Cindy said.

“You afraid of it, baby? There’s nothing to be afraid of! Here, let me show you.”

Rich gently rolled on top of Cindy and got up on his knees, straddling her.

“See?” he said, “It’s all good. Nothing scary, babe.”

Cindy looked up at him shyly, and then stared at his cock. She really did look terrified, and sexy and beautiful at the same time.

Then, she slowly snaked her legs around his back, opening herself completely to him. Rich got down on top of her, and, supporting his weight with his arms, kissed her gently. I could see the head of his steel hard cock grazing the moist, sensitive, fleshy folds of her entrance. Cindy was squirming.

I took in the visual, horny, and hungry – starved, for more to happen. For an instant I was my buddy Rich, and could feel Cindy’s soft entrance on the tip of my own cock as she squirmed. Involuntarily I thrust my own hips forward trying to enter her. My boxers were soaked with precum. I was desperate to feel that first plunge… Cindy could barely contain her anticipation, and she lay quivering, waiting for more.

But then Rich got up.

“Hey baby, I best get going,” he said.

“Wha…” Cindy looked alarmingly confused.

“Bri here needs to get to sleep.” Rich slowly stood up, and, retrieving his white boxers from the foot of the bed, slid them back on.

Cindy looked at me with daggers in her eyes.

What the fuck?!? I hadn’t said anything. For all I was concerned, Cindy was his for the taking.

“I’ll see you kids in the morning, OK?” Then, Rich left the room, his cock still very erect. As he was leaving, he glanced over at me with a cocky smile and a raised eyebrow.

Cindy almost broke down in tears.

“Brian why did you make him go away? Why didn’t he stay!!!” she cried at me.

“Huh? I –”

“You’re always so jealous and ruining everything for me. He’s just your best friend. Why couldn’t he stay?! I hate you!” And then she started crying.

I lay beside her and tried to comfort her. My hard on had long vanished, but my feelings of sexual frustration and humiliation lingered.

“Don’t touch me!” she said, angrily. She refused to talk to me or even look at me for the rest of the night.

I lay there, confused, thinking for a long while about what had just happened.

Yet again, Rich had had the last laugh. And deep inside, I knew what I was going to do next.

I was going to ask my best buddy Rich to fuck my girlfriend, and I would beg and plead if necessary.

I felt so dominated, so loathsome and pathetic, and hated myself for it, but I had absolutely no choice. It needed to be done if I wanted my relationship with Cindy to last.

(to be continued…)

Feedback, comments, thoughts, criticism are all welcome. It’s always a pleasure to hear from readers. Leave a comment, or read what others had to say here, or email me at :

-- Andrew J

Check out my blog at

Copyright 2006 Andrew J ( All Rights Reserved.