As I finished college, I wondered if I could pick up with Jeff where we'd left off. Last summer we'd gone from old high school buddies to best friends - with blowjobs.
Although we spent most of our spare time together, watching TV, or playing tennis or golf, or riding our bikes around, just two best friends hanging out, the cumming-in-each-other's-mouths business had started to change my feelings for him a bit.
And we had topped last summer off with a cherry, so to speak: I had wanted to make our last day before we headed off to our respective Senior years in college special, so I offered him my ass for the first time.
It proved more enjoyable having him inside me than I had imagined it would be. Then we had gone into the bedroom and I had taken him from behind. It was heartfelt too, not just pistoning in and out of his ass but wrapping my arms around him and kissing him on the back of the neck while we fucked. At least in my mind, it was a lot like having sex with a woman I really liked, and this really cemented my feelings for Jeff.
During my final year of college, I then put those feelings aside, focusing on not just my studies, but all the trappings of being a Senior. I found myself with a busy social life and ample dating options: I went out with and sampled several lovely women -- and a couple of lovely men too. Among the women, Janelle was especially hot. She was cute and spunky both in and out of bed, a combination you don't always get. We had some really fantastic sex for a couple of months, until we broke up over Spring Break.
After that breakup, I was too focused on finishing up the year to socialize as much, and was also starting to look ahead to my life beyond college. Would I get a job right away, or end up idle for a time while I looked? Get my own place? Move in with my parents? Find some housemates?
Hook up with Jeff again? Resume our "relationship," even? Speaking of housemates, I wouldn't mind being housemates with him.
I kinda hoped for these latter things and started thinking about them more and more as Commencement drew near. Looking back on that final day last summer when we'd explored each other so pleasurably, I would certainly enjoy picking up where we left off.
Shortly after I got back home, Jeff called me, inviting me to come on over to the apartment he'd just rented.
And meet his new girlfriend.
Okay, so much for the idea of getting "back together" with him. But I'd still be glad to see him.
Jeff and I exchanged a big extended man-hug, he seeming as glad to see me as I was him, though neither of us showed any acknowledgement of our prior relationship.
Then Tammi and I shook hands. Warm, soft, lingering an extra second.
She was a beautiful woman, stunningly so: permed blonde hair, blue-green eyes, clear skin, tall body, a little meat on her bones but not quite overweight, and I couldn't help noticing a very nice shape to her chest. Classic cheerleader looks. Hell, model looks, had she been thinner. Given she was my best friend's girlfriend, I wasn't going to dwell on her beauty, but I made a mental note of what a lucky guy he was.
"Nice to finally meet you, Joe. I've heard so much about you. Jeff knows how to pick 'em," she added, momentarily taking in my whole body with her eyes as Jeff went over to the fridge to grab me a beer.
"How can you tell?" I retorted. "You just met me."
"Oh, I know how to size a guy up." She said it deadpan so it wouldn't sound weird to Jeff, but she said it while her eyes lingered on my crotch, followed with a wink and a smirk.
Wow. Flirty, this one. Still, for Jeff's sake, I avoided engaging.
We hung out for a couple of hours, watched the day's ballgame on TV, generally had a good time. She asked me lots of questions, mostly in a friendly manner, but sometimes a little flirtatiously. She was that way with Jeff too, so I figured that was just her personality, and that Jeff was used to her being that way with everyone. Tammi was an amazing woman, not just pretty but quick-witted, outgoing, funny, smart. She really was the total package.
At one point she excused herself to the restroom, and Jeff whispered, "By the way, she doesn't know about ... you know," glancing down at my crotch.
Which was starting to feel warm now that both of them had ogled it today.
"... but I think she's interested," he added with a grin, just before she came back.
Whoa, what on earth did that mean? If he hadn't told her about us, what was it she was interested in? A threesome? Watching Jeff and me together? I wasn't sure what to think, but told myself to play it cool. Keep your thoughts out of your pants, Joe - and your dick in your pants.
As I left to go back home that night, Tammi was effusive again, hugging me goodnight while pressing her lovely chest up against me a little more than most women would, and even giving me a peck on the cheek.
Despite not wanting to dwell on Tammi's appearance and flirtations while I was in her or Jeff's presence, once I got in my bed I sure did. I wasted no time stroking myself, thinking about sucking on her tits, going down on her, and finally boning her, while Jeff watched.
As I came down from that, I started thinking about Jeff more, and what "interested" might mean. I was hard almost immediately again, provoking a second jerk session this time. This time I pictured a scenario where Tammi, not knowing our history, would "seduce" the two of us into touching, then sucking each other. I could just about taste his beautiful cock on my lips again. The fantasy culminated in Jeff fucking me slowly from behind while I ate my own leftover cum out of Tammi's pussy.
Damn. I had to admit that if that's what "interested" meant, so was I.
I didn't see them for a few more days, and then they invited me over again for a little barbeque. This time Tammi was a bit less flirty, but still her usual witty and charming self. As we were finishing up, she said "let's play a game!" Sure, sounded great. She looked through the game shelf in the hall closet, and came out with that game - sorry, no trademark names here - where you shake up a little plastic box of cubes with letters on them, and try to form words. Longer words are worth more points. I'm sure you've played it, and "gobble" up my meaning.
"Let's make it interesting," she said slyly.
I'm not much of a gambler, but if she wanted to play for a dollar a round or something, I could go along.
"Whoever gets the least points each round has to take off an item of clothing."
Oh my. I wondered if we'd stop when we all got naked, or if Tammi had further plans.
Clearly, if there were any plans here, they were Tammi's.
She lost the first round, shedding her blouse and revealing a lacy white push-up bra framing some lovely cleavage, and just a hint of nipple showing through. I had to admit to myself that this gave a little flesh, as it were, to the previous nights' fantasies.
Tammi asked, "Like what you see, Joe?"
"You're a beautiful woman, Tammi,” I said, deadpan.
I looked over at Jeff, who was wearing a sheepish grin. Guess he wasn't offended.
"Nice answer," she replied with a sour smirk.
I lost the next round, and doffed my shirt. "Joe's got a nice looking body, doesn't he Jeff?"
He just nodded, again sheepishly.
Jeff lost the next game, making us now both shirtless.
Tammi lost the next two, first losing her shorts, leaving her bra as the next item to drop. "Enjoy the show, boys." She scooted her chair back a bit, leaned forward to emphasize her cleavage, and reached back, unclasping and very slowly pulling the bra forward as her breasts fell out, dangling slightly. They were nice B-cups, incredibly supple-looking with very erect, pale pink nipples. I was hard as a rock.
As Tammi shook the dice for the next round, her breasts wobbled and bounced sensuously. I tried not to look, but Tammi locked eyes with me and smiled.
Jeff lost this time, leaving him down to underwear with a clear bulge under it.
"Joe,” she asked, looking pointedly down toward Jeff’s pointed underwear, "do you notice how much Jeffie is enjoying our little game?”
I stammered, "Uh, yeah. Sure looks like it."
Tammi lost the next game, which meant she was about to be fully naked. She stood up and paced a few steps away. Still facing away from us, she slowly pulled her underwear off. She faced us, threw her panties to me and slowly sauntered back towards us in her full-nude glory, clearly relishing being the object of both our male attention.
Jeff suggestively asked, "So what happens if you lose again, Tammi?"
“If anyone who's already naked loses again, they have to do something ... that I decide. Even if I'm the loser." She flipped her hair. "Who's going to argue with a naked beauty?”
Tammi suddenly seemed to have an increased focus on the game, nailing the next few rounds, picking up six-letter and even some seven-letter words neither of us guys would likely have come up with. I wondered if she'd been sandbagging earlier so she could taunt us with her naked body.
"Tammi, I think you're better at this than you've been letting on," I ventured.
"A girl never tells.”
After a pause she added, “and ... I'm better at a lot of things than I let on."
I lost the next two games, ditching my shorts and then my underwear. When I took off my underwear, despite my attempts to think about baseball, an erection sprung out.
"Nice cock Joe! That's a beauty," exclaimed Tammi.
"Way to go, Joe," added Jeff, smiling. "Looking good."
"Of course, nothing you haven't seen before, is it?" asked Tammi.
Jeff and I exchanged a nervous glance.
"Oh, men! Always so homophobic! I realize you haven't seen him in that state before."
Ha! What little she knew. Not only had I seen his dick in that state, I'd had it in my mouth in that state, more times than I could remember. Even had it up my ass, once. But I wasn't going to tell her that. Yet.
"About time you did, though," she added in a low voice. Good thing I was sitting down again, so she didn’t see my dong almost hit the underside of the table.
I lost the next round. There was a moment of silence. Being already naked, I looked at Tammi and asked, "So .... what do I have to do?”
"Glad you asked, Joe," she replied with a smile, standing up and walking over to me, her swaying breasts inches from my face.
"You have to suck on my tits for one minute. While Jeff watches. And times it.”
I looked to Jeff for confirmation that this was okay. He had the biggest wide-eyed grin on his face.
Okay, I could do this. Clearly, he wanted to watch me with his girlfriend.
I leaned forward and kissed one breast, moving my mouth over one of the nipples and opening it to suckle. She gave a loud moan of approval. I was only using my mouth, trying to stick to her directions exactly, but she implored, "use your hands, Joe."
I grabbed both melons, squeezing them gently and holding them in place while I worked them over. She whispered affirmations: "Oh yeah, Joe, that feels great ... squeeze them together now ... suck harder."
Towards the end she grabbed my left hand and moved it to her pussy. I only had a few seconds left, but I massaged around the outside, found her clit, and slipped one and then a second finger inside (provoking moans of approval), just asJeff called time. Tammi composed herself and said, "Ooh, thanks for showing Jeff how to pleasure a woman."
I don't think they noticed, but that comment softened me just a bit, because it seemed like it could be a tad insulting to Jeff. He was eating all this up, though. I'd heard about cuckolds before: was that what this was about? Having me fuck Tammi while he watched, maybe taunt him about it? I was down with the fucking part, but not so much the taunting part.
Jeff was my best friend - more than that, if I was honest - and I wasn't going to do anything to hurt him. I would keep a close eye on things, and if it ever looked like he was getting hurt I'd stop. I'd have to: no matter how hot she was, I knew I'd fully lose my erection if I thought he weren't enjoying it.
Tammi's game was still on fire. Jeff lost two in a row this time, exposing his lovely erection to us all on the first loss, then he had to get instructions from Tammi.
"I want you to lick and suck all of my pussy juices off Joe's hand. For one minute. I'll time it."
"You okay with that, Jeff?" I asked.
"Sure, anything for you two." He knelt down next to me and took my hand in his, then started licking. Then he sucked the two sticky fingers in his mouth. He looked into my eyes just like he was blowing me. I had to admit it was pretty damned hot.
Tammi was squirming in her chair: "Oh yeah baby, suck those fingers like you're sucking his cock." His eyes dropped to my cock for a moment, and I sure hoped it would replace my fingers in his mouth before long. Tammi continued, "Ooooh, that's what you really want, isn't it? He's you're best friend. Show him how much you love him." He sucked my fingers even harder. "Oh yeah, suck your buddy's big hard cock."
And we played another round. Jeff lost yet again.
"Okay Jeff, this is it, the moment we've all been waiting for. Now you have to suck Joe's ACTUAL cock, not just his fingers. For three minutes. I'll use the game timer."
I didn't think I'd last that long.
He knelt in front of me, boring his eyes into mine and starting with a lick up the underside of my cock, then swallowing me whole in a single stroke. He gently bobbed up and down, never losing eye contact. It was a straightforward blowjob, but a good one.
Tammi was almost losing it, now openly rubbing her pussy in the next chair. "You've always wanted to show your best friend how much you love him, haven't you Jeff? You dirty boy, I knew it. I love it. Fucking awesome. I bet you wanted to do that all last summer, but you didn't have the balls." Again, how little she knew.
"Speaking of balls, suck his." So he did for a few seconds. "Oh yeah, that's it. You give him the best blowjob he's ever had. That's a real man's cock you're sucking. It's all you've ever wanted, huh?" He kept sucking. The timer still had a ways to go, and I started to feel pressure building.
"Are you going to cum, Joe?" I could only moan. "Good! Jeff, you need to drink Joe's cum and swallow it. Take it all, you naughty cum slut!" He started sucking harder, and Tammi came over and started kissing me.
That did it. Her soft tongue probing my mouth, and his soft tongue licking my manhood, were too much. I tensed for what seemed like an eternity before finally exploding in his mouth. Even though I'd been stroking myself multiple times the last few nights thinking about Jeff and Tammi - both for the sake of that fantasy, and so I wouldn't be as horny when I saw them - I came a huge volume. It was as if I'd been saving it up all year just for Jeff. He swallowed eagerly, almost frantically to keep up with the flow.
The timer had run out. "Come on boys, enough games,” Tammi said, leading us naked down the hall to Jeff's bedroom. She laid back on the bed, exposing her spectacular body to us, open-legged, urging, "Eat me Joe, now." So I did. I savored the softness of her pink outer labia, the peachy juiciness of her inner sanctum, and the rigidity of her little clit. I paused to lick down below her pussy, where her juices had run down onto her thighs and butt cheeks.
"Oh yeah, Joe. That's how a man eats a woman. Watch and learn, Jeff."
Soon she was bucking and writhing in orgasm. I felt couple of gushes of fluid as she did, something I've never experienced before, or since. It wasn't a lot, certainly not like the squirting you see in porn (which we all know is fake, and intended to excite ignorant teenaged boys), and it wasn't pee either. But something sure came out. Tasted good to me.
She wasn't done. "Come up here and fuck me, Joe."
I had to pause for a second here. "Jeff, you okay with this?"
He nodded. I decided the question was important enough to ask again. "Listen, I'm about to have sex with your girlfriend. I need to hear you actually say you're okay with it."
Tammi sat up a bit, eagerly awaiting the response.
"Yes, Joe, you are my best friend and I want you to fuck my girlfriend. I want to watch you fuck my girlfriend."
To Jeff she said, "tell him you love him, and except for sucking his beautiful cock you have never wanted anything more."
"I love you Joe, and except for sucking your beautiful cock I have never wanted anything more than watching you make love to my Tammi."
Tammi had me lie on my back, and climbed on top of me, "Ohhhh, now that's a cock! Isn't it, Jeff? You'd know, it was just in your mouth! This cock is sooo much bigger than yours."
Now, this was patently false. My average-sized prick is actually a bit smaller than Jeff's. A fact that, again, I knew most intimately.
So this was just part of their little cuckold game. She was clearly into it, and so apparently was he. Okay fine, how could I complain, with the most beautiful woman I'd ever been with riding my dick and dangling her delicious melons in my face? I sucked on them eagerly, and she started grinding her pelvis against mine - I could actually feel her engorged clit on me - as I slowly rocked my hips up and down, side to side.
"Oh, that's magnificent, Joe. Better than Jeff. Maybe because Jeff wants you more than he wants me."
And, oddly enough, that brought her to a climax. Still, she just came down from her plateau, now golden with sweat, and kept rocking those hips and moaning as if she hadn't come.
Soon she was bringing me to another orgasm. Smaller than the first, but I definitely felt some real jets squirting into her.
"Oh yeah, Joe, shoot me up with that love juice. That's how it’s done. Okay Jeff, come on over and clean me up. Eat a second load of your friend's cum. This is the only pussy you get tonight"
He got between her legs and started licking. "Tastes better with cum in it, doesn't it? I bet you’d drink his cum every day if you could," she wheezed as she reached a third orgasm.
Still, little knowing that last summer he actually did drink my cum almost every day.
I was dismissed fairly quickly afterward. What a night! I admit, after I got home, I came three more times just reflecting on it.
One downside of this amazing evening was I hadn't gotten any contact with Jeff's lovely penis. After that loving blowjob, I really wanted to return the favor. I wondered if Tammi would allow that, or if she wanted me to keep playing the manly-straight-guy role and him the cuck. I'd be happy to reverse those roles, but I suspected that might not work for her.
Consequently, I guessed that while she might allow this to escalate to me fucking Jeff in the ass while she watched, she probably wouldn't want to watch him fuck me. Which I very much wanted to do, after that first time.
The more I thought about it, the more it concerned me how she seemed to really got off - I mean, it actually was what brought her to orgasm - on putting him in a submissive position, not only cuckolding him but even emasculating him just a bit. I wasn't sure I could go through with another threesome. The sex was almost certain to escalate: would the put-downs escalate too?
After that encounter, I wanted Jeff more than ever, in the purely sexual sense. Even though I couldn't be in a relationship with Jeff, the threesome had opened a door ... could I get together with him, without her presence and direction steering him into subjugation, to simply enjoy each other's bodies freely?
The answer would be yes.