Bobby Big and Tight - Ch. 3
Preface: This is the continuation of a true story. It involves a friend and me and happened two years ago when we were seniors in high school. Both of us were eighteen at the time. If descriptions of teen sexuality bothers you or offends you, please read no further
I.
There was little I could do to repair what remained of Bobby's and my friendship. At a moment of intimacy, I had recoiled from him in both fear and anger and now three weeks had passed without a word spoken between us. We still saw each other in school, but neither of us would so much as recognize each other's presence. Already our friend's had begun to notice.
"What's up with you and Bobby? You pissed off at each other or what?," a few classmates had asked. I shrugged it off and told them we had a little beef but that it was not a big deal.
Of course nothing could have been further from the truth. I was obsessed with our estrangement and could not understand why. Sure Bobby was a great guy to hang with, but I had lots of friends and girlfriends with whom to spend time. But because Bobby and I swapped spit and actually drank-in each other's cum, our friendship had taken on a larger, more complex dimension.
Our last time together had ended in nightmarish fashion. After Bobby had given me the greatest turn-on in my young life, I rebuffed him when he had requested anal sex. I felt I had been used and thought that the only reason he pleasured me was to get inside my ass. With Bobby being so well endowed, I was frightened too; I was pissed and I thought I didn't need him any more.
But now I was having second thoughts and for a strange reason. Every time I thought of Bobby I had a weird sensation. Not in my arms or on the back of my neck but actually down between my butt cheeks. Intellectually, I had no interest in having his immense cock in my ass, but subconsciously and physically it was all my body was now responding to. I tried to think of girls, but somehow it always came back to Bobby.
In fact, I remember during the time Bobby and I weren't speaking, I went out with a girl I had once fooled around with at a pool party when I was a sophomore. The only reason I thought of asking her out again was because two years earlier, after swimming, we had taken a shower in the cabana and while we were lathering up, she had soaped up my asshole and finger fucked my for about five minutes while I was doing the same to her pussy.
Now here I was, turning down sex with my best friend in the world, while at the same time desperately searching for girls who would play with my butt. What was going on with me? So after a while and after lots of thought, I decided to confront Bobby after school.
II.
Bobby always walked home from school the long way. Even after an arduous track practice, he got in a little more exercise by taking a 25 minute walking route home through a couple of neighborhoods. I knew where I could catch up with him so we could have some time together to talk.
Like clockwork, Bobby turned the corner of Rowley Terrace at about 5:00 pm after track. He saw me just as he turned the corner. I could tell he was thinking of turning around, but instead, he just stopped and stared - forcing me to come to him.
"Let's just be honest with one another," I said as I approached him.
"Hey, I'm the one that's been honest and you're the one that's changing your mind all the time," Bobby responded.
"Its not as simple as that. When you wanted to do 'you know what' I felt pressured and you didn't give a crap," I said as we both were now walking together along the sidewalk. We began to speak more quietly so that even the nosiest of neighbors would not hear us. I continued, "I know you Bobby, and I think you set me up. You weren't interested in us, you were thinking about yourself"
Bobby frowned and then began to grin, and said almost under his breath, "You know me too well".
"What does that mean?" I asked.
He went on to tell me the whole sorted story.
Apparently the girl Bobby dated off and on, Maureen (the one I kissed once), was great in bed but she was not interested in allowing him to have anal sex with her. I did not hesitate to remind him that such an aversion was perfectly normal for most women, especially high school girls! That being as it may, Bobby began to think about nothing but anal sex. He said that over the course of two months he started to keep a log of all the girls with the best asses in school and after awhile started including guys on the list too.
He wasn't particularly worried about this growing obsession until one date with a freshman girl (who he was fooling around with behind Maureen's back); he came close to physically forcing her to do what he wanted. The poor thing was so excited to be going out with a senior and he almost sodomized her!
He was horrified and knew he had to deal with this growing need quickly. When he went back to his list of "best asses in school", mine was apparently the top guy on the list. That is when he first thought of trying to fuck me.
"So in a way, you're right, Jonathan," Bobby finally said, "What happened at the lake wasn't by mistake it was more by design. I've been needing someone for so long now, I guess I kinda picked you, but I knew it would happen unless it came about kind of like by accident."
So that was it, I thought. Bobby was using me after all. But instead of feeling angrier, I actually now felt closer to Bobby than ever before. He was being honest and that counted for something, I guess. I was now to the point that my needs were becoming as physical as his.
I stopped walking and said. "Now that I know what's up. I'm cool with it. If you still want to do it, then I'll do it. But I don't want to get hurt."
"Are you bullshitting me?" Bobby asked disbelievingly.
"No, I'm real. We made a deal that we'd help each other out on stuff like this and I'm still in if that's what you want. But like I said a couple of weeks ago, we don't know what we're doing. I don't know how you're going to fit. What if I get hurt or bleed or something, that's what I worried about," I said.
Bobby was obviously excited. He started to walk quicker and talk faster. "Don't worry about that, I bought a tape that is really amazing. It has two queers in it but it still shows you how it should be done."
I now realized that Bobby was totally fucked in the head. He was talking about a gay sex tape as though it was a video of his favorite NASCAR race. And he talked about homosexuals in the far-removed and derogatory third-person. I thought it strange that he referred to them as "queers". If so, what did that make us? Or more to the point, since I was the one to get fucked, "What did that make me?"
He told me to come over on Saturday night at around 7:00. His folks were heading to the shore again and he needed the day "to get ready".
III.
Bobby met me at the screen door Saturday night with a Rolling Rock in one hand and a large glass of vodka and lemonade in the other. His hair was still wet from his shower and he stood before me in bare feet - shirtless - his chest still beaded with moisture. I had to admit to myself that he looked pretty sexy.
"Great, you're here. I was just making some drinks. I thought you might need two of them, just in case," Bobby laughed.
"I'll have the vodka, why waste time," I said.
Bobby said, "I thought you might not show."
"Hey, I'm you're bud, right?" I asked.
He smiled back and said, "Yeah, I know you are. And a pussy too".
We both laughed as we went into the kitchen where we sat at the table drinking quickly.
After about a half hour of small talk Bobby went on to explain his plan, "Now that we're all honest about this stuff I can tell you that when after what happened between us three weeks ago I got to thinking that you were right. I had no business making moves on you when I had no idea what I was doing."
The vodka and beer started to have its effect on both of us and as our inhibitions waned, so did our polite language.
Bobby continued, "If I had tried to fuck you that night I'd probably have ripped you in two. When you fucked me up at the lake the only reason it didn't bother me much was because your dick's smaller and I'd been practicing."
"Practicing? What the fuck does that mean?" I asked, completely taken aback.
"Well, it's embarrassing, a year or so ago I started fingering myself when I beat off. Especially when I came home drunk and it was tough to get off, I'd do a little something extra. After a while I used stuff in my room to fuck myself and it felt great. That's why I wasn't screaming while you were doing me. Shit, your dick's smaller than mine, but it ain't puny you know. Didn't you think it was strange that I barely flinched when you pushed inside me?"
"Actually, it never even crossed my mind. I've never fucked my own butt, so I just never thought of it," I said.
Bobby kept on with the plan, "Any way, after what happened, I went out and bought a tape of a bunch of gays having sex. I got it when I went into New York for that school interview. It's called Anal Party or Anal Hardy, whatever. But one of the scenes has just two guys in it and it kind of goes through the preparation and stuff that will loosen you up for me to fit. I thought you could watch the video as we went through the steps."
"Wow, you gave this tons of thought," I said.
"I just wanted to be prepared, in case you changed your mind - and you finally did. Why don't you take a shower and meet me in my room," Bobby said as he grabbed two more beers from the fridge. I took one to the shower with me.
IV.
While in the shower, I had scrubbed myself well, especially around my asshole and butt. I wanted to make sure I was "presentable" as though I was a hooker about to go out with some hotshot CEO.
When I dried off I put the towel around me and went to Bobby's bedroom. His comforter was laid out on the floor and his TV and VCR were also on the floor next to the comforter. Also there were a couple of throw pillows. The lights were low and he had lit some candles. By the time the sun went down it would be just the glow of candles and the blue flash of porn TV.
Bobby came up from behind me and took my towel off. He was now in a pair of cut off jeans, barefoot and shirtless still. I could tell by the way the front of his shorts hung that he was wearing no underwear. I stood there totally naked.
Bobby said, "Come over here and I'll turn on the tape"
He lead me to the comforter as the video started.
On the screen were two gorgeous blonde guys in their very early twenties. They had perfect surfer bodies, one had a big cock and the other had an enormous cock. I couldn't believe that there existed such singular perfection, never mind two of them together. My next thought was that they couldn't really be gay. How could they be? I bet there were tons of chicks trying to hit on them all the time. They probably were just doing it for the money, I thought.
The two guys on the screen didn't talk much but it became clear that the guy with the enormous cock was going to fuck the other guy. (I later came to learn that the guy doing the fucking is called a "top" and the guy getting in the rear was the "bottom"). The Top lead his cute friend to a rug beside a fire just as Bobby had lead me to the TV.
In front of the televised fireplace were some pillows and the Top asked that his bud lie face-downward on the pillows - which lifted his ass ever so slightly into the air. As I watched this on TV, Bobby motioned to the pillows next to me. I was to do what was happening on TV. I knelt beside the pillows, lowered my crotch down onto the pillows and laid flat. Like the Bottom on TV, I was lying in the middle of a room with my crack in the air.
It was almost surreal to watch what was to happen to me play out thirty seconds sooner on the TV in front of me. Following the tape, Bobby lathered my back with baby oil and gave me a tremendous back massage, relaxing my body from neck, to shoulders to my lats, down to my lower back and butt.
Just like on the television, when Bobby got to my bottom he started to pay close attention, added more oil between my cheeks and became very precise in his technique. Slowly, Bobby centered all the action of his hands and fingers to my ass, pushing, probing and prodding.
At first his fingers just slid in and out of the crack, but after a while he began to push his index finger into my hole. He did this for as long as they did it on the videotape. By this time, my eyes were shut and only once in a while would I look up to see what was happening on the TV. I noticed that the Top had switched to two fingers and soon I could feel Bobby slowly introducing a second finger into my butt.
I lay there silently, utterly relaxed, with waves of pleasure flowing all over my body.
Suddenly, though, Bobby fingers were removed and replaced with something colder and larger. I opened my eyes to see a dildo being worked into the butt of the Bottom on TV. I raised my head to look around at my own rear. Bobby was sliding a well-oiled carrot in and out of my ass. The tip was narrow and made for easy entry, but as it went deeper it also got wider. With each thrust I felt it enter slightly deeper. The carrot was the perfect choice to expand a virgin hole wider and wider.
Once I got used to it, I again closed my eyes and listened intently to Bobby's breathing, to the groans on the TV and to the sloshing of the carrots oily in-and-out.
The tranquility was broken by a loud slap from the TV. I looked to see that the Bottom's ass was alternately being massaged and slapped. Suddenly, I, too, felt the painful smack of a well-place hand. I was about to sit up, but Bobby had beaten me to it by quickly shifting his position from beside me to a position straddling across my back with him facing my feet. His weight was completely on my back even as he continued to manipulate my asshole. My muscles were still so relaxed that I couldn't muster the energy to kick him off.
"Hold still, this only lasts a minute. You'll like what comes next," Bobby said.
Even as he said this, the pain continued. He wasn't just slapping me on my rear, but right on my bung hole itself. The relaxation of my body laid open my cheeks wider than they had ever before and Bobby had a clear shot to slap his fingers hard against my sphincter. It hurt, but was pleasurable at the same time. Although I'd tense up a bit with each crack to my hole, I'd relax totally again with each exhale. My ass was on fire and I didn't know how long I'd be able to bear it.
When I looked again at the TV, I saw the Top lean down toward the Bottom's asshole and lick it delicately once, twice, three times. In seconds, I felt Bobby, from his straddled position lean over my bottom and run his tongue deep inside my crack. It was the most magnificent thing I had ever felt and almost shot a load onto the pillows below me. Bobby licked a few more times and I could feel his rough tongue right on my hole, pressing hard, mixing saliva with oil and the sweat from my crack.
Having finished licking me, Bobby got up and moved behind me. On TV, the Top was stroking his penis to make it long and hard in preparation for entry. Bobby was undoing his fly and already his cock was fat and thick and ready to take me.
Like the guy on TV, Bobby loaded his dick with oil and moved his tip to the outside of my ass. He started massaging my cheeks as he slowly pressed his cock-head against my resisting butt hole. Slowly, it started to go in. Bigger than any carrot or finger, Bobby's cock consumed my entire ass with a splitting, fiery pain of pleasure. Even as he entered and pushed in, I could hear his breathing getting faster. When he was just three-quarters of the way in, the pain was so intense that I was about to try to get him off me. But before I could do anything, Bobby grabbed me tightly and said softly, "Jonathan, I'm cumming."
Although Bobby didn't move an inch, I could feel his cock beginning to pump by itself inside me as the warm milky cum filled my insides. The feeling was indescribable as his cock just kept pumping fluid as though he was taking a piss inside my ass after a long night of drinking.
As the pumping slowed, Bobby rolled off to one side taking me with him. I was now on top of him, with my hard prick in the air. Bobby was below me with his cock still in my ass as he took his oily hand and began to beat me off. After three or four pumps of my shaft, I was spewing over the both of us.
We laid on the comforter totally spent as the videotape continued on to a new fag scene where two very young looking boys were giving each other blow jobs in a penny arcade. We were too dazed to watch and quickly fell asleep in a drunken-sex induced haze which lasted until morning when I had to get up early to meet my family for Sunday services.
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