tagFirst TimeTom's Torture

Tom's Torture


[Author's Note: For those following the adventures of Tom Lenovo, the story about to transpire below takes place approximately six months after Tom's incestuous dalliances in the chapters entitled "Katy's Boobs." However, the reader is welcome to enjoy this plot independently of the other if so desired.

I would like to dedicate this story to my sexy new muses, Kelly and Pam. Thank you for the stimulation and inspiration, ladies!

Despite the fog rolling into San Francisco bay on this chilly December evening, I felt warm and invigorated as a lustful surge of blood flowed through my body. With singular determination, I ignored the scenic sights of Fisherman's Wharf as equally as I did the panhandlers on the corners, walking briskly and eagerly up from the transit station to a certain building about three blocks away. This certain building contained a small one-bedroom apartment, and within this apartment a beautiful 18-year-old girl was waiting. Waiting for me, a very horny guy not much older than 18 himself. And when I arrived, or hopefully soon after I arrived, this beautiful girl was going to give me perhaps the most incredible and generous Christmas gift any girl could possibly give a guy: her virginity.

The girl's name was Pam, and we had been dating for about three months. We had met on the first day of registration at a large university in another big city, never mind which. There we were, random bodies in a throng of confused and excited college freshmen all trying to figure out what books to buy, where classes were and all the other chaos a freshman must endure. I was going one direction, Pam another, and our collision sent books and backpacks scattering across the floor. After hurried apologies, we'd finally gotten a look at each other and that was that. Classic boy-meets-girl. We got to talking, realized we were both new to the school, and it wasn't too long before I worked up the courage to ask her to coffee.

From that day, I'd say we fell instantly and crazily head-over-heels in love with each other. Everything just clicked, and to be honest, I was all to eager to finally find myself in a "normal" relationship with a girl who was not a relative. I had just moved on from a rather torrid summer affair with my sexy little 18-year-old cousin, Katy, and also—amazingly—her mother, my aunt Ellen. While from a sexual standpoint it was one of the most incredible experiences of my life, the three of us knew that any normal, ongoing relationship was simply out of the question, so to finally have a pretty girl on my arm who wasn't related to me was wonderfully refreshing.

The funny thing was, in getting together with Pam, I had to almost completely throw back the clock of sexual maturity that I had so swiftly evolved into with my carnal experiences with Katy and Ellen. You see, Pam was a virgin. An honest-to-God virgin in the 21st century. Of course, I hadn't known this when I'd first met her, but after a couple of dates, when the after-dinner make-out sessions became more and more heated, she'd breathlessly and almost apologetically informed me that she had never gone all the way with a guy.

Now, she'd told me this while straddling me on my bed in my dorm room, her skirt hiked up, her panties wet and bunched around her pussy, with my raging hard-on desperately bulging within my pants and grinding against her covered labia. To say I wasn't, well, call it "deflated" by this news would certainly have been a lie. But even in this heated moment of passion, I actually found myself admiring this girl more.

A virgin. The girl grinding on top of me was a virgin. I took a deep breath and reconsidered the picture before me. Pam was blond, petite and sweet. She was very skinny but still had a nice subtle flair to her hips that stood atop long, very long legs. The breasts I had been allowed to feel up over a shirt and bra were small but very pert, with nipples that seemed to want to pierce right through all the shielding of satin and cotton. Probably the most striking thing about Pam was, interestingly enough, her mouth. When amused, Pam would spread the widest, brightest grin I had ever seen, flashing beautiful, neat white teeth. A hint of dimples and flashing brilliant blue eyes accented this wonderful smile and completed a perfect package of sweetness, sexiness and mischievous innocence all at once.

I was hooked.

But as indicated earlier, I was no virgin, far from it. Actually, for this day and age I could be considered a late-bloomer too, having lost my virginity only very shortly after my 18th birthday. Since that time I have been with just four women, including my brief and incestuous affairs with my cousin and my aunt. And as puberty continued to pump enough hormones through my body to drive an elephant crazy, I knew that I definitely had a stronger sexual appetite than most guys. It was pretty much all I thought about, all the time. Oh, I know what you're thinking: ALL guys think about sex all the time, especially teenage guys. Well, just let me someday tell you more about how I nailed my own first cousin and aunt, then I think you'll get a better idea of just how far I was willing to go to get what I wanted....

That said, I wanted Pam. Badly. But I also realized how much I actually cared for her. It was incredible. From day one we had been two peas in a pod, hardly separated except to go our separate ways to our own dorms to bed at night. In the first week of school we'd hastily rearranged our schedules so that we had almost all the same classes now. We clicked perfectly on every level, and I couldn't complain.

What cheered me up even more was the fact that Pam wanted me too. She told me as much after waiting for the initial news of her admitted virginity to sink in. "I just felt it was fair to tell you, Tom," she said, looking lovingly down at me and caressing my face. "I just never gave into the pressure of giving it up to some guy just to be cool, all through high school. And as the years went by and I realized I could wait until someone truly special came along. Someone like you, Tom. But...just not quite yet."

Then we kissed. Not much else we could do after that speech. And although I went to sleep that night with a serious case of blue balls (even after masturbating and blasting a load of cum nearly halfway across the little room), I slept deeply and happily, because Pam had also promised with all her heart that her Christmas gift to me would be her virginity....

* * *

All girls seem to develop their own strange rules about when and where and to whom and how they're going to finally let a guy put his cock in her, and often there is no rhyme nor reason. As guys, all we can do is try to be in the right place at the right time. For Pam, even though she had decided to let me be the first guy to make love to her, the first barrier that needed to be broken before hymen was her age. She wanted to be officially an adult, 18 years old. Well, her 18th birthday had been a week ago, and finally we had arranged for the time and place for the next barrier to be broken: a certain little apartment in San Francisco, three blocks up from Fisherman's Wharf.

The apartment belonged to Pam's college roommate, Kelly. Kelly, much wilder and infinitely more worldly than quieter, more innocent Pam, seemed to have any amount of money she needed, whether from her rich parents or her collection of wealthy part-time boyfriends. She seemed to maintain a lifestyle like a slightly scaled-down version of Paris Hilton. For example, just for the two-week winter break, Kelly had somehow secured a fully furnished one-bedroom apartment here in a trendy section of San Francisco, and she had invited Pam to share it with her. I had been enjoying most of my winter escape with my parents back home, but I was dying to see Pam again, especially since I'd missed her birthday, and I had counted the days and even the hours before I could be on the flight that would take me to San Fran where I'd get the next 96-hours with my girlfriend. I assumed I'd be staying in the apartment with the girls, perhaps crashing on the floor, but I'd worry about that later. I had other things on my mind!

In what seemed like a blur of hugs and kisses and squeezes, I'd rung the buzzer, been let into the apartment, and thrown my bag somewhere, and the blur continued for sometime. Finally, both of us gasping for air, Pam and I broke our embrace to take a look at each other at last. I was clad casually in cargo pants, a loose button-down shirt with the sleeves rolled up, and an old, worn leather jacket. Pam was barefoot in tight hip-hugger jeans and a wonderfully thin white tank-top hinting at the black bra beneath. She also wore a soft wool sweater to keep the chill of the night off, but with one side sliding down to expose a pretty alabaster shoulder and collar bone.

"Where's Kelly?" I asked, hoping only for one answer.

Pam smiled at me. "She's out for the night." Perfect answer.

I stepped toward her again, "So...hungry?"

"Mmm...only for you, baby."

When she was my arms again, her body became lithe and eager; she pressed solidly against me, pushing her pelvic bone directly against the erection that had formed in my pants almost as soon as I'd walked in the door. I responded greedily, groping and squeezing her ass and breasts and any other fleshy body parts I could find. As we sucked each others tongues and petted heavily right there in the middle of the living room, I couldn't help but let out a giddy chuckle. I had been under some silly old-fashioned romantic notion that our first love-making session would be slow in building up: candles, soft music, perhaps a bottle of wine....

No way, we were getting it on. NOW. As if to squash any remaining doubt in my mind—or hers for that matter—Pam suddenly pushed me backward into the corner of the oversized L-shaped couch. And there, standing over me with that huge and now seductive grin, Pam said, "You just sit and watch, big boy. And stay hard."

"Oh, that won't be a problem," I said, quickly shucking off my jacket.

I realized in that moment that some groovy music had been playing in the background and to its pulsating beat Pam began to strip down before me. First the sweater dropped to the hardwood floor, and this was quickly followed by the tank, peeled right up her skinny little body. Her small breasts were shielded by the tiny black bra. With a wink, Pam reached back and undid the clasp. It was to be a night of firsts, beginning with this one: I was now looking at Pam's boobs for the first time.

With only a twinge of guilt, I couldn't help but compare this moment to the first time I had seen my cousin Katy's boobs, about six months before. I couldn't help but compare because for the rest of my existence I would compare ANY woman's breasts to those of my cousin's. Why? Oh, dear reader, you just have to trust me: they were quite possibly the biggest most perfect breasts on the planet. They were the stuff of legends....

But I was NOT comparing Pam's much smaller titties negatively. No way. Pam was simply adorable, as were her breasts. They were just enough for a nice handhold, as pert as I had imagined, and neatly peaked by sharply protruding pretty pink nipples. I would very much enjoy sucking on those babies in a few minutes.

Pam, her inner vixen suddenly unleashed, gave her own nipples a nice pinch, groaning erotically at the sensation. She looked at me. "You like?"

"Oh, fuck yeah. I like!"

"Then I'll show you some more...but get those fucking pants off first. And that shirt."

Happy to follow orders, I quickly stripped off my shirt and wiggled out of my pants and socks. I was now sitting there showing off a nicely tented pair of boxers to my horny girlfriend.

"Ooo," she cooed. "That's nice. My boy's got a nice body. My turn to show off."

She turned her slender back to me and began to unbutton her jeans. I licked my lips, half-expecting to feel saliva running down my chin. Torturously slow, Pam began to gyrate her hips in small circles as she began to work the tight jeans down over her rear. As they came down, I took in the sight of one of the most perfectly proportioned asses I had ever encountered. Soft white firm flesh made up each cheek of that beautiful ass, the crack itself teasingly covered by skimpy black thong panties.

Pam glanced back at me, putting her finger to her mouth and giving me a playful "uh-oh" look. "Is this too much for my big boy? Should I stop?"

I gave my cock a squeeze through my boxers. "Baby, don't EVER stop!"

She grinned. "That's what I thought." And with that, she got her fingers into the strings at her hips and began to push downward, slowly, oh so fucking slowly, until at last, in glorious detail not three feet from my hungry eyes, my girlfriend Pam exposed her completely naked ass to me.

I swallowed, fighting to keep from jumping up and biting right into that ripe flesh. But I stayed right where I was. Pam had a plan, all of it worked out in her head to make this special for both of us, and I instinctively knew that for what was to transpire I was to obey her every command.

In time with the music, Pam bent over, rubbing her hands up her long, smooth thighs. In her position, I could see right between her legs to a perfectly shaved pelvic mound. My God, I could make out the swell of her labia, and I could swear, I could fucking swear, I saw a glint of moisture right along her slit. When she turned, I was able to confirm that my girlfriend was completely shaved down there. Her entire vaginal region was baby-smooth and ready to be consumed. I felt a swell of pride, honor and complete satisfaction for the fact that I would be the first man to enter that glorious zone.

Pam saw exactly where I was looking and looked down at herself as well. She said, as she traced a finger along her slit, "My big boy's been so patient, waiting for this...I can't wait to give it to you."

I swallowed again. "Pam...you're so beautiful."

She smiled, that wonderful grin, and slowly sank to her knees in front of me. "Thank you, Tom. I feel so comfortable doing this in front of you. It's so liberating." Then she began running her fingers up my thighs. "Now...let's see what's going to be inside me soon...."

She eased down the top of my boxers, and I shuffled my hips a little to help her progress. Presently, my cock was exposed to her, in the naked flesh, for the first time. Pam actually paused, and I watched as she blinked in what I could only describe as surprise. She finally said, "Oh...my fucking God, Tom...it's HUGE!"

I could only grin, proudly.

Pam finally got my boxers all the way off, and we were now 100% naked with each other. Reluctantly, and with almost holy reverence, Pam slowly and gently tried to put one hand around my shaft. Her fingers just barely touched once her hand was all the way around it. I moaned, as did Pam, who said, "Jesus, Tom...I sensed that you were big when I felt you through our clothes, but...you really ARE my big boy, aren't you?"

Again, I could only grin. It was quite difficult for me to form words at this moment.

Pam gave me a gentle stroke, and then another. Even this slight movement was enough to produce a couple small pumps of pre-cum that drizzled down from the head of my cock and onto one of her fingers. Pam leaned forward and gave the pre-cum a testing taste with her tongue, sending shivers up my spine. "Mmm," she said, licking her lips. "My first taste of boy. Oh, this is so exciting, Tom!"

"Oh yes...Pam." I felt drunk, stoned, completely out of my wits.

Pam got her other hand around my cock and stroked slowly, lovingly. "There are so many things I want to do with you, Tom. I want to suck you, taste you...I want you to suck me, and taste me! But first I must uphold my promise, I must give you my gift. Are you ready to receive my gift to you, Tom?"

"Yes. God yes!"

"You're surprised, aren't you, baby? You knew I was a virgin, but you didn't know I would make this so wonderfully kinky for you. How do you like it?"

I could only groan half-mumbled words. "Pam...oh please...."

That wonderful smile again. "Okay, let's see if we can do this. I have no idea how I'm going to fit that monster in me...but there's only one way to find out...."

She got up from her knees and made as if to straddle me. I had a feeling that this wasn't going to be the easiest position at first, but again, this woman was in charge right now. If she wanted her first penetration to be while she was on top, then so be it! But somehow, in the haze of lust that was consuming my entire being, I remembered that a certain degree of responsibility was called for. I reached over for my pants, to get at my wallet. I got it out and was feeling for the condom wrapper when Pam's hand gently stopped me.

"It's okay," she said softly. "Knowing that this day was coming, I went on the pill a few months ago. We'll be safe, and when I feel you inside me for the first time I want to feel ONLY you...every vein, every degree of heat from your flesh...."

And with that, Pam finally got up on her knees on the couch, straddling me. I placed my hands on her naked hips. Her flesh felt warm, but she had goose bumps. Was she nervous? Just cold? Probably both. But further logical thought was abandoned once I felt her lower herself gently along the length of my penis, pressing it into my own belly. With a seemingly practiced talent, Pam gently slid her pussy up and down along my length. I felt her vaginal lubrication oozing its moisture all over my cock and into her pussy lips. Jesus, once I was in there, I didn't think I'd be able to last that long.

Pam seemed to read my thoughts. She stroked her fingers in my hair, still sliding back and forth, getting us both wet and ready. "Baby," she said, "when it happens, I don't want you to worry about anything. If you cum quickly, it's okay. I understand. I don't know how long I'll be able to take your size in me the first time anyway."

I nodded, feeling relieved. It always seemed to be the case with me, the first time in a new pussy was always too much. It was no marathon. With time, however, with the other women, I was pretty proud at how long I could last....

Now Pam was raising herself up again, reaching down to grasp at my cock. She aimed it upward, touching the pre-cum-lathered head against the entrance to her wet pussy. She said, "We shouldn't have to worry about a mess, either. Four years on my high school gym team took care of that. There's no way a girl's hymen can last after the first couple of falls against the balance beam. So get ready, my sweet boy...here we go...."

Down, slowly, slowly down...Pam eased her weight down, and I began to feel the head of my cock squeeze tightly into her pussy. An inch, perhaps two...and then a pause. I looked up at Pam; she had her eyes squeezed tightly shut. Her teeth were clenched. My teeth were clenched, too, for that matter. I fought for control and waited, letting my girl take her own time, get used to the fill, the girth of my cock. It was exquisite.

"Oh, that's tight," she groaned softly. "Oh, my big boy...please be patient with me, oh please...." She eased down just a bit more, taking me about a third of the way in. She rose up a little to let the lubrication work its way around us, then gently back down again, back to that third, and then another pause. "Oh...it's so good, Tom. Just...really...really tight...thank you for being patient...oh, thank you, Tom...."

Patience had nothing to do with it. I had to fight every carnal fiber in my body from the urge to thrust my hips up and jam my cock right up to the hilt inside her tight cunt. I clutched tightly at her hips, hanging on for dear life.

"Okay," she panted, "a little more...just a little more...."

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