Chapter 1: Meeting Janey
Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Reluctant, Cheating, First, Oral Sex, Anal Sex, Masturbation, Size, .
Desc: Sex Story: Chapter 1: Meeting Janey - Jim is a mature college freshman who undertakes to seduce Janey, a senior. He advances one base at a time until he finally scores. His path to success has satisfying diversions with busty, young Debby and obese Eileen and, devirginated and on the pill, Janey has her own diversion.
Wherein I meet lovely Janey and begin my campaign to conquer her overwhelming fear of pregnancy (and her virtue). My initial success is limited to receiving a reluctantly administered hand job.
I'm sure that my parents thought that Janey was an old-fashioned 'plain, nice girl'. No doubt her parents thought the same except for the 'plain' part. In fact they were likely all correct.
I met Janey on a train returning from a college football game. She was a senior and I was a freshman but one who had worked some years before enrolling. I was therefore older than she a bit chronologically and a lot in terms of life experience.
She shared my bottle of rum with dainty sips at first and, as the night progressed, with some serious swigs. This was a bit surprising since we were both drinking directly from the bottle and chasing the raw liquor with coke. Between drinks we kissed, somewhat chastely at first but as the alcohol (or was it my lip-skill) loosened her up her mouth opened to admit my tongue. Four hours later we were back at the college, our tongues tired from wrestling and my balls swollen and aching from the extended arousal. And that was far from the last time that Janey left me in that condition.
As I said, my parents thought Janey was a plain, nice girl. She wasn't really that plain but neither was she a beauty. She was a natural blonde with blue eyes and a wide, full-lipped mouth. She was big but not fat. And, although she dressed in ways that disguised them, she had large breasts. I'm a tit man so this was a bonus for me. It took months to get to know them but when she finally let me play with them I had fun. They were soft, somewhere between firm and floppy and she was at least D-cup. But more about them later.
For more than two months I saw Janey at least three times a week and most of those times resulted in aching, swollen balls and a self-administered hand job. We usually ended up against the wall of her college residence as we tangled tongues in extended goodnight kisses. I'm better endowed than average and she must have felt the bulge in my pants that I kept pushing into her belly. Except sometimes when, standing in a dark corner of one of the college buildings I would get my thigh between her legs and use it to rub her pussy through her clothes. I don't know if I ever brought her off that way but I do know that I was able to rub my erect tool against her and blow a messy load into my shorts.
I couldn't get my hands below her waist but she only made token resistance when I slipped my hand under her sweater to feel her brassiere encased breasts. And they felt great. More than a handful and her flimsy bra was easily pushed up so I was able to fondle the lush, soft fleshiness. Her nipples were a study by themselves, long, thick and rubbery hard, like little cocks sticking out and up from her somewhat saggy boobs. And after that first feel she sent me a signal that she liked it as much as I for whenever we were just going nowhere special, i.e. for a necking session, she didn't wear a bra and I had full access to her marvelous mammaries, albeit only underneath her sweater or blouse, but it added to the frustrating pleasure of almost making out with her.
I took her to my home at Thanksgiving but the weather was lousy so we couldn't go outside and the house was too small for privacy so I didn't even get in a good petting session. Christmas though was a milestone of sorts. I went to visit her at her home and each evening had the opportunity for some comparatively uninhibited 'necking'. Finally, on my last night there, I got my cock out of my polo pajamas and forced her to hold it. The result, after five nights of swollen balls, was an almost immediate explosion. I think I blasted semen all the way across the room and I think that occasion laid the groundwork for future successes.
"Joe! Oh No!" Janey gasped in shock when she felt and saw the creamy jet blow from my cock. "No! Don't ever do that again!" But although her words were those of protest her tone was one of uncertainty, almost timidity.
I expected that when the new term began I could expect regular handjobs and maybe get the chance to reciprocate. Such was not the case. Not for a while anyway.
"Please Janey," I begged. "Just hold it."
We were in a corner in the deserted entryway of the science building and I had one hand under her sweater fondling her heavy breasts. My other hand was trying to force her hand down to my crotch but she was resisting as usual.
"No Joe, I can't. I'm scared. I'm afraid of getting pregnant."
"But Janey? That's silly. You can't get pregnant that way."
"I know but... but I'm afraid of what else you'll want?"
"Please Janey... you know I don't want you to get pregnant... not yet... not until..." but I didn't finish the sentence. She could fill in the remaining words, "we're married", but I had no intention of making that kind of commitment yet. Unless it was the only way I could get into her.
"But... but Joe?" Her resistance melted and she let me push her right hand down under my sweatpants.
"Yes, Janey. Oohhh yesss," I moaned as her fingers touched and then seemed to explore my throbbing tool. I didn't have to hold her hand there any more so, hoping she wouldn't notice, I carefully I unfastened the button at the waist of her skirt eased down the zipper.
"Easy darling... don't move your hand," I cautioned. I was close to an explosion but I didn't want it to happen yet. I'd taken my left hand from her breast and had that arm around her, holding her close while my right hand was poised to dive under the waistband of her skirt.
"Oh God, darling... it feels so good," I whispered and Janey's mouth opened to another kiss. Her tongue tangled hotly with mine and she uttered a throaty whimper and then I quickly slipped my hand down under her skirt and panties to cup the furry mound between her legs...
"No! Stop it Joe! You can't!" she exclaimed in a loud whisper and she tried to pull away but I locked her body to mine so that her right arm was trapped and her hand was pinned against my cock.
"Please don't... let me go," she pleaded but my fingers were busy in the wet, slippery and incredibly soft fleshiness of her pussy. There's nothing softer in the world than the swollen, slippery flesh of an aroused woman's cunt. For a moment I thought she was sobbing and then I realized that she was panting like a steam engine. My middle finger was nestled between her cuntlips and I angled it inside her to the first joint.
"Don't hanh Joe hanh... let me hanh go," Janey panted but her legs were looser, more open to my marauding hand and then abruptly her hand closed around my tool and squeezed it. She was no longer pinned by my body but she didn't try any more to back away. I stroked and finger-fucked her cunt and began to fuck her hand, savouring my victory over her inhibitions.
"Hah anh hah anh hah anh," she panted and as I struggled to hold back my climax she uttered a choking whine and her body slumped down so that she was held upright only by my cunt-cupping hand. At the same time her hand squeezed my cock in such a stranglehold that I couldn't have ejaculated even if I wanted and her hips bucked and jerked. I could feel the pulsing and bulging of her pussy in my hand and her vaginal mouth contracted on my finger as she was wracked by orgasm. For a moment I felt as triumphant as if I'd just got her cherry but then my own needs took over.
Still holding Janey's quivering body upright with my cunt-cupping hand I pushed down my sweatpants with the other and angled my hips away from hers so that my throbbing prick was free and out in the cool air.
"Hanh... Joe... hanh... what're you hanh doing?" she asked as I manipulated her fingers around my erection.
"Make me cum darling... move your hand," I begged and with a sob she did as I asked. Her hand was warm and as she moved it back and forth I fucked it. I felt that huge heat in my groin and this time was better than the other time she'd sort of handjobbed me. She wasn't squeezing like when she came but her hand was far better than mine. My own knees quaked and I think she felt the beginning of my climax and she began to milk me.
"Yeeahhh... oohhh God Janey yessss," I moaned as I felt the brief but also endless surges of sensation as I went off. I continued to fuck her hand and she continued to milk me for almost a minute before I bent down and kissed her slack-lipped mouth.
"Joe? Oh Joe? Look! What'll I do?"
Janey's tearful question was triggered by the sight of the gooey mess on her skirt. When I went off some of my gism had hit there and she was understandingly worried that it would be seen. And people would know. We managed to clean it somewhat and before she went back into her dormitory I gave her my jacket so she could hold it across her thighs and hide the stain on her skirt.