Emma & Barry

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Virgin Emma seduces her gay best friend.
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Sexually, I was a bit of a late bloomer. I didn't lose my virginity until the summer after my senior year in high school, when I was almost nineteen, long after all my girlfriends had gained enviable amounts of experience.

I had a boyfriend, Barry. The first thing you should know about Barry was that he was gorgeous. He was on the swim team, one of the best swimmers at the school. His body was muscular, but sleek instead of bulky. The sight of him in a pair of wet Speedos was enough to make any girl damp in the panties. Plus, he knew how to dress and groom himself, skills in which most guys at my school were sorely lacking. Barry wore the best clothes, the best colognes, had the best haircuts. He always looked good and we looked good together.

The second thing you should know about Barry was he was the nicest guy I had ever met. He was kind, considerate and fun to be around. He treated me real nice. We were literally best friends. When I saw some of the jerks and lunkheads my girlfriends ended up with, I considered myself lucky, despite the third thing you should know about Barry which was, he never touched me.

We had been going together since the start of Junior year and in those two years we had three "real" kisses, he'd felt my tits up two times, and I'd touched his cock once. (It wasn't even hard at the time.) We had even slept in the same bed on many occasions, but still nothing. I tried everything I could think of. I got him drunk, I dressed like a hooker, I literally begged for it. Barry just said that he didn't want to do anything until we were married, an event which he promised was looming on our horizon. He even bought me one of those "promise rings," a very nice one.

I was dubious about this excuse because Barry seemed to have no moral qualms about anything else. He drank, he smoked cigarettes and pot, he swore like a sailor. Barry didn't have any religious convictions that I could identify, and he even sometimes made fun of the Christian kids at our school.

Still, when I saw some of the agonies that my girlfriends went through because of their sex lives, I almost considered myself better off. The pregnancy scares, the guys who "played" them, the stories about getting caught by their parents and being grounded for months. Who needed all that? Barry and I had been together for two years, more than twice as long as any of my girlfriend's longest relationships, and I thought that perhaps this was because we didn't have sex to ruin things. Maybe all those sanctimonious weirdos trying to sell us on abstinence had a point.

The problem was, I was horny as a minx. Someone had bought me a vibrator as a "gag" gift for my birthday. I'd laughed at the time, but eventually went through hundreds of dollars worth of batteries. Dates with Barry could get me so worked up, and since he wouldn't do anything about it, I'd have to take the matter into my own hands. I became an avid and creative masturbator, experimenting with water jets, anal stimulation and assorted fruits and vegetables. I could get myself off a dozen different ways, but I knew they were all just poor substitutes for the real thing.

Finally, at our Senior prom, I decided that I wasn't going to wait any longer. I wore a strapless sex goddess dress and made a point of slipping my panties into the pocket of his tux jacket, folded up like a handkerchief. (He looked like James Bond in his tux, by the way.) We slow danced all night and I whispered incredibly dirty things into his ear the whole time. After the dance, as a surprise, I'd booked a suite at the most expensive hotel in town. Hot-tub, champagne on ice, box of condoms in the bedside drawer. I'd even gone on a Mom's-credit-card spree at Victoria's Secret and bought some really high-class frilly slut-wear. I could have seduced the Pope that night. But not Barry.

That was the night that Barry told me his big secret, which I found out later everybody in the world knew but me. He was, of course, gay.

I was utterly shocked. Call me naive, but I had no idea. Whenever I'd tearfully spill the secret to a friend, they'd always say they'd known for months. Even my Mom knew. Upon learning that Barry and I had broken up, she said that it was for the best because I'd never get a real boyfriend if I hung around queers. Of course, nobody had thought to tell me.

Barry and I didn't speak for several weeks and I was in tears for my high school graduation. I missed him so much. Finally, swallowing my pride, I gave him a call. He said he missed me too, and that his fondest hope was that we could still be friends, like we were before.

Of course, it could never be as it was before, not with this between us, but I thought that maybe we could develop a new kind of friendship. Plus, even then, in the back of my mind there was the thought that I could somehow "turn him," win him over to the right side of The Force.

But then I met Barry's new boyfriend, Terry. Barry and Terry. How goddamn cute is that? They had been seeing each other for a while, even when Barry and I were supposedly together, but I elected to overlook this fact. It was important to Barry that Terry and I got along. "The two most important people in my life," he said. Whatever.

The thing was, Terry was remarkably easy to get along with. Plus, he was almost as hot as Barry. He was into track and field, and so had a whole different set of muscles from Barry's swimmer's body. Dark-haired where Barry was sandy brown. More boyish, whereas Barry had this kind of mature look that had always driven me wild.

We ended hanging out a lot. I liked going out with these two hot guys, being seen with them. The thing about gay guys is, they're almost just like girls, so it was a lot of fun. They both liked to shop, both liked to dance. The best part was, Terry's parents were in Europe for the summer, so we had this huge house on the lake to hang out in. I spent most of my nights there. Of course, when bedtime came around, the two of them went into Terry's room and shut the door, leaving me to cry and/or masturbate myself to sleep in the guest bedroom.

With his parents gone, Terry was also able to display his huge collection of gay porn. Pornos, straight porn that is, had never appealed to me before. Ugly, hairy guys with big cocks plugging silicone-injected Barbie dolls and coming all over their faces. That was supposed to be sexy? But gay porn got me hot. The pretty boys were almost always the "bottoms," sucking cock or getting fucked, and I would always identify with them, imagining myself being taken by some big-cocked manly man. Plus, I may be wrong here, but it seemed like the gay pornos had better production values. Better camera work, better sound, better acting, all that. That may seem like a small thing, but I was never able to get past the over-lit, cheapo video of regular porn.

Sometimes the three of us would sit around Terry's living room watching these things on his parent's big-screen TV. I know we were all getting turned on. Barry and Terry would sometimes retire into the bedroom halfway through the video, and then I could finally stick my hand down my shorts and stroke myself off. Still, it didn't seem fair.

One night, we were watching one of the videos after hitting Terry's parent's liquor cabinet pretty hard. I was more than a little drunk and so horny I was almost delirious. I looked over and noticed that Terry was stroking Barry's hard cock through his pants. Barry kept swatting Terry's hand away, embarrassed I guess to do anything in front of me.

"Don't stop," I said. "I want to see."

"No," Barry said, blushing.

"Why not?" I pressed.

"It'd be like my sister watching me," Barry said.

"I'm not your sister," I reminded him. "I was your girlfriend, remember?"

"Yeah, but . . ."

"If you won't do anything with me, the least you can do is let me watch you guys fuck."

"Yeah, right," Barry said.

"I'm completely serious," I said, and I was.

Terry started laughing hard. I could tell he was excited by the idea. Barry kept hemming and hawing, but with me and Terry both working on him and him already worked up with the liquor and the porn, eventually he gave in.

Terry undid Barry's pants and pulled his cock out. I literally gasped when I saw it. Barry's cock was huge. I'd known it was big, but I'd never seen it erect before. In fact, that was only the second time I'd seen an erect penis in real life. The first time was when I accidentally walked in on my step-father when he was masturbating years before. Barry was even bigger than Donald.

Terry stroked it lovingly. "It's a monster, isn't it?"

All I could do was nod breathlessly. They made out on the couch for a while, kissing and fondling, Terry's hands working Barry's huge prick. I loved watching them. My pussy was twitching in my soaked panties. I could almost hear it clicking and smacking down there.

"Let's go into the bedroom," Terry whispered.

They got up from the couch and, for the first time, I followed them into Terry's room. Terry had all these neon beer signs decorating the walls, and these provided the only light, gentle blues and reds. Terry put some Miles Davis on the stereo and they slowly began to undress one another. I think they were putting on a little bit of a show for me.

I sat in a butterfly chair in one corner of the room while the boys reclined naked on the bed. Terry's cock wasn't as big as Barry's, but it was standing at stiff attention. They lay beside one another, kissing and fondling for what seemed like hours. My nipples were so hard I thought they were going to poke holes in my tank-top. I was so wet it felt like I'd pissed myself. I was literally shivering with excitement, flushed so hot it was nearly unbearable.

Finally, Barry turned to me and said. "You can play with yourself if you want to, hon."

Permission granted, I tore my shorts and my panties off and threw them on the floor. I thrust my naked pussy into the air. My hand dove into the dripping wet hot twitchy spot between my legs. I wanted them to look. I wanted them to see. But they were completely into one other and paid me no mind.

I watched, not even daring to breathe for fear it would make me wake up from this dream, as Barry found a tube of KY in the nightstand drawer. He squirted a line onto his hand, and worked it into Terry's ass. Then he squirted more, all up and down the eight fat inches of his cock.

I thought Terry would roll over then, offer up his ass, but instead he lay back and spread his legs. Barry rolled on top of him and Terry wrapped his legs around his boyfriend's waist. I got out of my chair and kneeled beside the bed to get a better look. Barry reached down and grabbed his jelly-soaked cock to guide it in. I didn't think it would work. I thought there was no way that huge prick could fit into somebody's ass. But it slid in easily, just the fat head popping in at first, but more and more of the length with each successive stroke until it was buried to the hilt. Barry moaned. Terry grunted. I myself made a sound like a little squeak.

Barry fucked the boy beneath him. Terry arched himself back and up, to meet the cock that was plunging into him, arms and legs wrapped tight around his man. Both of them sweating and groaning, kissing each other hungrily. They had completely forgotten me, I could tell

Still kneeling beside the bed, I sat straight up, and brought my naked cunt down on the heel of my bare foot. I rocked back and forth, soaking my foot with pussy. I thought I'd tried everything, but I had never got myself off with my foot before. Watching Barry fuck the hell out of Terry, hearing the animal sounds of lust they were making, bearing my clitoris down hard on my heel, I came so hard I thought I was going to black out.

Barry was right on the verge, too, I could tell by the way he was breathing. He cried out and thrusted harder into Terry's ass. Terry moaned out the word "yes" several times, and Barry almost screamed. I imagined his cock spurting into Terry's tight little ass, and this was enough to bring me to a second orgasm, seconds after the first.

Barry pulled out, and discreetly wiped himself off with a washcloth they had thoughtfully left beside the bed. Terry just laid there with this breathless, just-been-fucked look. He still had a raging hard-on, but Barry soon took care of that. He bent down over Terry and took his prick into his mouth.

I had moved back over to the chair, so I could lean back and work myself with both hands. I would have thought that after two orgasms I'd be depleted, but my pussy was still just dripping.

I watched, fascinated, as Barry sucked Terry's prick. It was liking watching a virtuoso play a woodwind instrument. Barry obviously had lots of practice at this, which meant that he must have been sucking cocks the whole time we were a supposed "couple." I pushed aside this jealous flash so I could enjoy the show.

Barry slurped and licked; he nibbled and kissed. He used his hands as well as mouth, paying equal attention to Terry's cockhead and to the shaft of the penis. Barry fondled and licked Terry's balls and even his dripping asshole. It was an awe-inspiring performance. Terry's eyes were closed, lost in a world of ecstacy. He let loose an unmanly yelp as Barry took his entire prick into his throat, and then whined orgasmically as Barry sucked hard on just the head while furiously pumping his shaft with one hand.

Barry moaned, "Mmmm," as Terry collapsed limply, tears dripping from his eyes."Did he come in your mouth?" I gasped as I brought myself off yet again.

Barry gave me an open-mouthed grin so I could see the heavy cream coating his tongue. Some of it dripped from his lips down his chin. He leaned over and shared a spermy kiss with Terry.

I spent that night in their bed, Barry sleeping between us. In the morning I watched Terry give him a good-morning blow-job. After that, Terry made us mimosas and homemade eggs benedict and we went for a brisk nude swim in his pool.

It was then, me doing backstrokes while the two boys horsed around naked, their penises flopping around like sleeping snakes, that I came to an important decision. The night before had been awesome, no doubt about it. Their performance had been the coolest thing I had ever witnessed. I could have spent the entire summer like that, watching the pretty boys fuck. But I knew I'd get tired of it. I was no fag hag. I felt the same way about this as I did about sports; I loved to play, but as a spectator I got bored fast. I was a nineteen-year-old virgin, for chrissakes. My Mom was right about at least this one thing. This problem wasn't going to get fixed if I just hung around a couple of gay boys.

I needed to lose my cherry. I could have gone out and found some other guy easily enough, but I found that I didn't want to do that. I wanted Barry. For two years I'd thought of nothing except giving up my virginity to him and for two years he'd strung me along, leading me to believe that this would eventually happen. The cocksucker owed me.

As I swam, I formulated a plan as to how to make it happen.

Fortunately for me, Terry had a day job coaching track at a summer camp. Barry and I usually just lazed around the pool during the day while he was at work. It was on one of these days that I put my plan into action.

We were sunbathing by the side of the pool. I wasn't wearing a bikini top. Barry of course said that he didn't care, my tits didn't do anything for him, but I caught him looking a few times.

"How many cocks have you sucked?" I asked him.

"What?" He laughed nervously. "Why?"

"Because when you suck off Terry, you sure as hell look like you know what you're doing."

Barry dodged the answer for a while, but I was persistent. Finally, I got him to cough up a number. "Six."

"You've gone down on six guys," I said. "While, I should note, you were supposedly dating me."

"Come on, Emma," he whined. "You know how it is."

"Yeah," I said. "I know how it is. While you were out, getting your groove on with guys, I was at home being faithful to you. All my girlfriends have been screwing around all this time, but not me. When I finally do get with a guy, I'm going to be clueless."

"I'm sorry," he said.

"Don't be sorry," I said. "Teach me how to do it."

"Do what?"

"Suck cock," I said, rolling my eyes.

"No, Emma," Barry started to blush. He could be so weirdly prudish at times.

"You owe me that much, Barry," I said. "It makes sense that a gay guy would do that better than a girl. If I learned it from a fag, that would be at least one valuable skill I could bring to bed with my first guy."

"You're crazy," he said, but I could tell that he was going to do it.

My lessons began that morning, Barry demonstrating technique on bananas and popsicles, or anything else phallic we could find around the house. Then I would follow suit, while he criticized my style.

I did learn a lot. Barry was font of fellatric knowledge. He even wrote up a list of what he called "Cocksucking Commandments:"

"1) Variation is the key. Your lips, tongue, and even the roof of your mouth provide different kinds of texture. Don't just fall into the trap of repetitive head-bobbing.

2) The head of the cock is of course the most sensitive part, so that's where you should focus most of your attention. However, the shaft should not be neglected.

3) Don't forget the hands. It should always be a combination blow-and-hand-job.

4) THOU SHALT NOT USE YOUR TEETH!!!

5) Don't neglect the balls, but here GENTLE is the key-word.

6) Throating is an advanced skill, requiring practice, but is undeniably impressive. Don't rely on it too heavily, though. (See Rule #1)

7) Ass-play is essential. You can use a slicked-up finger or even (if you're nasty) your tongue. Straight guys might be put off by this, however. Their loss!

8) Get a sense of the man's rhythm. Know when he's about to cum. To prolong a blow-job into nirvana, take the guy right to the brink and then back off. Repeat this step as necessary, until YOU are ready to get him off. The more you prolong it, the more intense it will be, but be warned: jaws do get tired eventually.

9) When the man cums, for God's sake don't stop. You don't have to swallow (although a little protein never hurt anyone's diet) but you should at least let him finish before discreetly spitting into a napkin or washcloth. My own personal preference is to share the ambrosia with the man who provided it, but straight guys might not go for this one either.

10) Finally, don't ever suck off someone unwilling to return the favor. This only leads to frustration and resentment.

Good luck and good head!"

That day's lessons ended abruptly when Barry tried to demonstrate his deep throat technique on a banana. You can see how this would be a bad idea. I had to Heimlich him.

It wasn't until the next day, Terry at work again, that I could move my plan forward. Barry was really getting into his role as teacher. We sat on the couch as he lectured me further, illustrating key points with scenes from the pornos.

After this went on for a while, I said: "All right. Enough theory. How about some practice?"

"What?" Barry was sometimes deliberately dense.

"You know what I'm saying, Barry," I said. "I want to try it out on the real thing."

"I don't think that's such a good idea, Em."

"Why not?"

"Well, for one thing, I am in a relationship with Terry."

"Do I need to remind you," I said, ready for this point, "that you were in a relationship with me when you started sucking Terry's cock. Not to mention the five others. So your monogamy's not really the issue here."

"OK . . ." Barry said. "But, you're not exactly my type. I like boys, remember?"

"A mouth's a mouth, Barry. Just close your eyes and pretend I'm Tom Selleck."

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