I was a junior at Hampshire the night Jane came to me. It wasn't a good time. In my mind I was the World's Oldest Virgin, terminally unlovable. I'd even struck out with Easy Emily, who had fucked half my friends but not me even though I was the only person who actually cared about her. Years later I understood my feelings were precisely the problem she had with me, but at the time they were simply proof that something in the stars had aligned to render me completely and utterly unlovable. A terminal virgin. The guy no women would ever go out with.

I know what you're thinking, it sounds totally wrong. I wasn't six hundred pounds, in fact I was in decent shape thanks to the college weight room and long rides on my racing bike. In retrrospect I realized I had been my own worst enemy. But confidence is something you either have or you don't. I hadn't started out with a lot to begin with and what little I had Easy Emily poured down the drain. I was down and depressed, and convinced beyond all doubt that would absolutely, positively die a virgin.

Jane was just about my best friend at the time. Certainly she was my best female friend. I'd met her during freshmen orientation, and felt an immediate interest in her. She was about low average in height for a woman, with light olive skin and dark doe-shaped eyes hidden behind a big set of thick, round glasses. Her hair was dark, tightly curled and hung over her shoulders. And Jane was all curves. Voluptuous is the word for Jane. She liked tight jeans and tight button-down shirts that hugged her body. Her bottom was round and appealingly female, but her breasts really stood out, full and round from what I could tell, one of the best-endowed women in the entire freshman class. My freshman roommate and I often compared notes wondering what Jane would look like naked. But she kept her shirts mostly buttoned up and let her bulges speak for themselves. I wanted to date her from the day I met her.

But like most geeky virgins I was slow off the mark. I wasn't the first guy to ask her out. Chuck was. He lived down the hall and looked something like a blonde rock-god with his slender body, and long blonde hair. A couple girls even asked me about him since he and I were friends. But he asked Jane out right away and within a couple weeks they were an item. And so it was for the first two years at school. Chuck and Jane were together. Since Chuck and I got along well and I was seen as no threat, he didn't mind that Jane and I were friends. I became her confidante and learned about her relationship in intimate detail. Oh not everything of course, but Jane liked teasing and flirting with me because it made her feel good and I was 'safe'.

Their relationship was tempestuous, punctuated with vicious fights and passionate make-up sex, which I began to suspect were half the reason they fought. Eventually the pendulum swings grew too great and they broke up.

Finally, I imagined, I'd get my shot with Jane. After all, I was the guy whose shoulder she cried on the night they broke up. But I never raised the issue, in part because I felt the time was wrong, but mostly because I feared losing her. One of my roommates Bobby wasn't that shy. He was a popular guy, with long dark hair, a good sense of humor and bunch of friends. Jane went out with him and they quickly hooked up. Once again Jane was sleeping with the guy down the hall only this time I could hear them through my wall.

Listening to Jane's cries of pleasure did nothing whatsoever for my confidence. I spent the entire first semester either at the library or electronics lab. It was good for my grades, but at lunch Jane and her roommate Missy asked me why they never saw me any more. I just pretended to smile and told them I was too busy right then.

The thing about Bobby was that he was an asshole. He liked himself far more then he'd ever like anyone else and that included Jane. Given that he was also handsome, rich and quite personable no girl ever hung on to him for long. Including Jane. Which I found out one cold night at the beginning of Winter semester. I'd gotten back from the library tired and bored and headed straight for bed.

Then I heard a knock on the door. Then Jane's voice calling my name. And it was cracking like it had the night she and Mike had broken up.

Up I went. I flicked on the lights, pulled on on robe and went to the door. Jane pushed herself through at the first opportunity. She was crying, and angry, and almost pushed me aside in her rush to get inside. “That bastard,” she yelled. “Than fucking bastard.” She jumped into my arms and hugged me before I could even move.

With a free armI clicked the door shut. With the other I pulled Jane close. Looked like Bobby had yet another change of heart. They hadn't bothered me much before, but he hadn't dumped Jane before. The thought made me boil with anger at him, tempered by feelings of inadequacy I hadn't seen this coming. But I mostly just wrapped my arms around here and listened.

She sobbed for a little while, then reached for her purse, and pulled out a tissue. “I'm sorry I got you up. I know you've been working like the dickens. It's just he was such a dickhead.”

“What happened?” I asked while steering her away from the door. My room in the house was small, just room for my bed, desk and wide overstuffed chair I'd hoped to neck on someday, but hadn't managed so far.

“I came over and he asked me to blow him,” she said, wiping her red eyes. “He was acting weird, but you know how I love to do that for my man.” Then she shuddered for a moment. “Right after he came he told me to get the hell out!”

That stunned me. I couldn't believe Chuck would be that rude to anyone, much less to Jane. A wave of anger came over me and I could feel my muscles tightening. I turned to the door.”

Jane must have noticed. 'Now, sweetie no. I don't want that. I just don't want to be alone right tonight.”

“Okay,” I said, not entirely sure where this was going.

“Can I sleep with you?”

“Sure.” What else could I say?

I dropped my bathrobe and clad only in pajama bottoms pulled on my bed. Jane peeled off her shoes and set her glasses on the bedside table and rolled in next to me. I lay on my side and darned if she didn't push her nice, round bottom right up against me.

Naturally, my virginal penis shot immediately to attention.

And I was mortified. Here I was with my friend who came to me for comfort and support and the first thing I do is pop the biggest, most throbbing hard-on I'd had since the day I discovered lesbian porn. And her bottom is rubbing right up against it, wiggling too as she settled in. I keep my arm to myself but very quickly recognize that Mr. Hard-on was not going away in the short term so there is not a chance in hell of me catching a single wink like this, much less forty. So I backed away a few inches, so Mr. Prick won't feel my quite babelicious friend and get the wrong idea. Plus I really didn't want her to think of me as just another user, especially after what she'd gone through that night..

Naturally Jane scooted right over and pressed her oh-so-firm bottom right up against my pole, and wiggled once again as she settled in. So I inched back a bit more, and Jane wiggled right up next to me. Then I inched back until my back was against the wall. Jane scooted her sweet tush right up against me. With no place left to retreat I was stuck there with my erection pressed quite firmly against her. And every time I wiggled for comfort it rubbed against her, so I forced myself not to move. At all. Naturally that didn't work very well.

Unfortunately, I also had no place left to put my left arm, so I draped it over her hip, and around her stomach. Jane reached down, took my hand in hers and lifted it to rest right on top of her right breast.

This led to a brief bout of panic, as I debated my base desires, my friendship with this very special woman, her pain of rejection balanced against the fact that she was pressing her tush up against my throbbing member, which was hard enough to lift weights. Combined with the fact that she herself had placed my hand atop her amazing bosom it occurred to me that she might be coming on to me. The mere idea made me ashamed. No way Jane would want geeky me when she could have anyone she wanted. I told myself she only wanted comfort and assurance.

My moral stance did not change the feeling of her bottom pressed against me and her breas beneath my fingers. Which led to an inner debate between desire and virtue. Virtue argued she was hurt and you should never, ever take advantage of a friend's vulnerability. Vice counted witht the fact that she herself had placed my fingers around her full, round bosom. Did that not imply a limited permission to grope? Virginal desperation eventually won out. And so I extended my digits and began to feel through the heavy material of her bra and blouse.

Nothing happened, except for the thrills of pleasure shooting up and down my cock. I fondled, gently, and felt around for the slightest sign of arousal. A hard nipple say, or a sigh or perhaps resumed rhythmic wiggling of her bottom against me. No such evidence appeared. But Jane raised no objections either so I continued my amateurish caresses and smelled the floral fragrance of her brown hair. I rubbed my nose against the back of her neck and shoulders. Her skin was so soft and smooth, her hair so silky, and I fought the urge to lick her.

Then under my finger I felt a nub. I had uncovered a nipple! I swirled my fingertip around it. To my delight it swelled under each new touch. I rolled it between my finger and thumb like I'd read about in those Penthouse magazines I kept under my bed. I squeezed her breast between my palm and fingers, and stroked the tip of her nipple.

Jane sighed and pressed her bottom against me, rolling it slightly. That encouraged me to extend my tongue and lick the back of her neck. She moved again and her hand closed over my pawing fingers. But she squeezed me and did not pull away. She turned her head slightly, and her hair fell away from her ear. She'd once advised me that girls liked having their ears licked, so I traced the back of her left ear with my tongue. I moved from the bottom to the top, then ran my tongue inside her ear. She cocked her head slightly to make it easier for me to lick her. That seemed an unmistakeable 'go' sign. I continued, not wanted to hurry the pace, not wanting to be pushy, just trying to savor this sweet moment with this supremely desirable woman who seemed to be enjoying yourself.

Then she pulled away, rolling on her back. I panicked fearing I'd gone too far. Streetlights shined through the window, silhouetting her in a dull orange light, but I could see her bosom rise and fall. “You have a nice mouth,” she said running a fingertip around my lips. Naturally I licked. Jane closed her eyes and let out a soft sigh when I sucked her index finger into my mouth. She let out a very soft sigh, a little more then a whisper and said, “I should have done this years ago.”

She sat up on the side of the bed and looked at me. I couldn't see her eyes, but I knew she was watching me, and more then capable of seeing the tent in my pajamas. Jane began to unbutton her blouse and tossed it aside. A moment later and she reached behind her back to undo her brassiere. She flipped it aside as well, letting her breasts fall free.

And there they were, every bit as full and wonderful as I'd imagined in my private fantasies. Her breasts were wide at the based and capped with small, pale nipples that reminded me very much of the fabled pencil erasers. There they were real and naked before me. She stood up and peeled of her jeans, wiggling as she pulled the tight fabric over her hips. Clad only in her panties she slid in next to me. I took my left hand and took her head in my hand and bent over to kiss her.

He lips were soft and liquid, and tasted of peach balm as I pressed against them. They were smoother and softer then I'd imagined. After a few moments her lips opened. I accepted the invitation and pushed my tongue between them. Her taste was salty, perhaps a bit of Bobby's sperm but that really didn't matter because I was kissing Jane's mouth, and feeling Jane in my arms, and felt her full, beautiful breasts pressed up against my chest. My whole body tingled and felt myself pressing against her, as we kissed. I felt the small of her back and traced the line of her spine, and ran my fingers through my hair as she kissed me back, hard, ardently.

Her right hand slid inside my pajamas and she squeezed me. “You have a nice cock,” she whispered. And my hips pumped as she touched me. She took her other hand and pulled down my pajamas, releasing my erection. Then she bent to kiss me again harder, and started to pump me.

My hips thrust in time with her hand, and I so appreciated how different her touch was then my own, more gentle, tentative, but softer and wonderful in a different way. I thrust my tongue deep as I could into her mouth in time with her hand. Then our kiss broke and she straddled my right thigh. She ground down on me, whispering “this is how girls do it” in my ear. I took her bare breasts in my hands, full to overflowing and she bent over to press her left breast to my lips. I licked around her nipple, grazed it with my teeth then took it between my lips to suck, and caress it with my tongue.. Jane let out another soft cry and began to grind herself against my thigh, hard, and I pushed back, also hard, as she rubbed herself on my.

She began to let out a small high pitched cry with each thrust, and I risked a gentle bite on her nipple which led her to let out another cry and push her breast against me. So I mixed little bites and swirling lips, and her pumping hips picked up speed. She pressed hard against me, very hard and I had to push back hard to keep my thigh up but she picked up speed, then finally wrapped her arms around me and let out a long, groan before collapsing against me. I wrapped my arms around her and held her. She leaned back and I could almost see her smile as she asked, “Sure you're a virgin?”

“Yeah,” I said, but for the first time seeing real light at the end of that very long tunnel. “Have you done it with a girl before?”

“A couple times,” she said. “ Remember I told you I'd met really cool girl in Italy last summer?”

“I still have the letter, but never guessed. Did you do it with her?”

“Uh huh,” she said in a way that implied clearly pleasant memories. “I knew telling you would turn you on. I've been through your porn stash.”

I felt mortified again, but realized that I really liked feeling her on top of me,. “When did you do that?”

She leaned back, stroked my forehead and gave me a little kiss on the lips. “When we were studying for the Econ 304 midterm and you went out to get pizza. I dug under your bed and found your stash. I saw which pages were dog-eared.”

“You're sure a lot better then any porn.”

Jane giggled for a second before adding, “So are you. I should have done this when we first met.”

“I wished you would have!”

“Mike asked me out first. I wish it had been you insstead..” She stood up then and peeled off her panties. She took them in her hand and rubbed them on my face. “Smell me,” she said. “Feel how wet you made me. How you made me cum.” And I sniffed and could feel the moisture on the damp fabric before she threw them aside. “I think it's past time I took your cherry,” she said. Then she knelt over me and took my cock into her mouth.

There's an epic difference between sleeping with a woman who enjoys sex and sleeping with a woman who adores oral sex. Jane fell in the latter category. For her sucking a cock wasn't just a distraction, something you did to get the man ready for you. For Jane it was a main event. She wrapped her lips around my shaft and slid down, down down until she somehow got all of me inside her mouth, then held it there. I could feel her tongue against my shaft and especially as she withdrew and licked around the head, and up and down my shaft. She kissed my cock, rubbed it on her cheeks, licked it like a lollypop then swallowed me whole again, squeezing me with her soft lips, setting a steady rhythmic pace. And I thrust into her mouth. She'd thrust for a time, then rub it against her face and lips, wrap it in her hair and pump, before swallowing again. She worked me fast and slow and all I could do is pump my hips in time with her fingers and sweet sucking lips. Soon I began to feel my cock tingling, my balls filling and I knew I would unload soon. So I warned her as I had been trained.

Jane giggled. “Are you going to give me a creamy drink?” she said. “I'd like that you know, to swallow all your balls can give me. I tasted a few drops and it was good.”

I was good with that and told her so. Her grin widened then took a wicked turn. “This is your first time sweetie, so I want you in my pussy. And I want it to last.” She let my swollen, throbbing and wet cock fall. She straddled me and slip up my chest, leaving a long track of juices on my belly and chest. She placed her knees on each side of my head and held her lovely, hairy pussy right over my face. “Don't you want to taste me too? Lick me like my Italian girlfriend?”

Of course I did! I took my hands and placed them on her hips as she lowered her pussy to my mouth. She held it just above me, leaving my room to move as I extended my tongue to touch the very bottom of her slit. She was juicy, tasted faintly of musk as licked up and down as slowly as I could possibly manage. I licked up one side and down the other, then pushed my tongue between her moist, pink lips and pushed it as far as it would go. My fingers squeezed her bottom and she began to move, and I followed her lead, trying to let her guide my tongue with each pulse of her lips. I rubbed my nose on her mound, and traced the crack of her ass with my fingertips. And her pussy lowered and she began to grind herself on my mouth, pushing hard against my lips as I pushed back with my tongue. I felt her hands in my hair as she rode me, riding me as she might a horse in full canter, grinding her sex against my mouth and leaving it sopping with her juices. I could see her breasts swaying in time with her hips, and then she tossed her head back and gave out a long, low groan as she pushed herself hard against me. And through my tongue I could feel the spasms of her body as the came hard and fast, then slow and gentle as her orgasm subsided.

She rolled off me and lay at my side for a moment, legs spread wide open, breasts heaving as she breathed. “God, I wish I'd seduced you years ago,” she said. “Then I wouldn't have dated those two assholes.” She leaned over and kissed me, licking her juices from my lips. “I taste good, don't I?” she said.

“Best ever.” I said, rolling over to take her left breast in my mouth.

Jane held my head in my hands and whispered. “Of course I'm the best ever! I'm your first.”

I raised up and told her how glad I was that it was her. She kissed me again, hard and I felt her hands on my hips, guiding me between her legs. “It's time you got busy and fucked me.” she said. And I felt her hand reach down to take my cock. She opened up her legs and began to rub the head of my cock on her slit.

“Does it feel good baby,” she asked, and I could only moan my response. She guided me so my shaft ran across her lips as my hips involuntarily thrust against her. She threw her head back and moaned as my shaft found the opening to her sex. And with one push I was in to the balls.

I wish I could describe the sweet slick muscles of her pussy, gripping my, riding me. Or her hands on my hips holding me, pulling me in deeper. Or as she pulled her legs back and bent them to get me inside as deep as I possibly could. Or how she sounded moaning my name as I drove into her again and again. I could not last long, but I lasted long enough to hear her urging me on, begging me to fuck her, asking me to fill her with my cum. Her words made it quicker, I felt the pressure building, the tingling in my shaft, the pressure in my balls, the pressure building in the base of my shaft that I tried to hold back. Only this orgasm would not be denied and then the sweet spasms came. I cried out and pumped my load into my friend, my sweetheart, my first lover, my Jane. And I heard her cry in response as I filled her, and thanked me for it.

I collapsed on top of her but she did not care, asking me to stay inside her sweet, sticky pussy. “Thank you, “ she said. “Are you sure you're a virgin?”

I laughed softly, the weight lifted from me. “Not any more. Thanks to you.”

Jane kissed me and licked my neck. “My pleasure. And you best get used to having me around.”

I felt my softening shaft begin to slide from her. Jane kissed me softly again, tenderly, but held me in place on top of her. And I knew from that moment on Jane was far more to me then any friend. And she still is today.