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.