I went to small HS, 60 some people in my graduating class, looking back I’m not terribly ashamed I didn’t date, too few options.
I bounced around schools, Art institute of Seattle then a local community college then University of Oregon with too few dates. Ironically, I’m not an ugly guy, just a little shy and there’s been more than a few girls who liked me. I just took my dear sweet time dating just like when it came to finishing college.
I met this one girl, Ashley, cute blonde but significantly younger than me and it bothered me. She was a senior in HS when we met, somewhat annoying to be honest. She happened to a friend of a friend and would go to our shared friend’s parties. She’d follow me around annoying me and I’d mostly just try and avoid her. I ended up dating her end of summer after she graduated, she saw me as a way for her to lose her virginity and I was still unsure of her. I honestly regret not sleeping with her but she gave me my first real taste. I visited her at her college, and we began fooling around. I had her almost naked, just in tight fitting underwear sitting on top of me. Our banter continued, she answered a phone call from her dad while I teased her by kissing her breasts, and she teased back.
I build up the nerve to go down stairs on her with my hand and in all honesty had no idea what I was doing other than attempting to get her off. In retrospect I know she enjoyed it but it was a failed attempt. Even through nervousness the inner sexual being eased out as I held my moist hand to have her suck on my fingers provacatively.
She returned the favor and started kissing me on the chest and ventured lower and lower. My heart rate was through the roof. She sweetly asked, “Yes?” as she reached for my pants. Seeing how all this was new to me, I was already half way to orgasm. I probably replied to something to the effect of “YES!”.
Ashley had openly admitted to me she had an “Oral fetish”, my naivity didn’t feed my male instincts had it should of. She had blew about four guys before me, which I’d later learn and I could have gotten pletny of action from it. Lesson learned.
As laid outstretched on her college dorm room bed, barely unpacked, I just couldn’t help but think, “This can’t be happening”. I was slightly embarrassed, I’m not a big guy, being somewhat short and of course in all things proportional I’m just averaged sized in well, I’ll just say it: 5 inches erect.
She pulled down my pants, then my underwear, I layed there feeling slightly exposed and she grinned. I wanted to watch but closed my eyes thinking, “I want this to last as long as possible”. Soon as her lips and tongue touched my the tip of my dick, I knew this would be short. She licked and proceeded to suck, bobbing her head, tongue rolling down the underside. I could feel her hair touching my thighs and her breasts resting above my knees. It felt like an eon, I was fighting the urge to cum as long as possible but in reality it probably lasted only two or three minutes. When I couldn’t take it anymore, I knew what was about to happen. I started to tense up, opened my eyes and I managed to mouth, “I’m gonna…” and began to cum.
There’s always that male instinct to over exaggerate how awesome an orgasm was, but this was it, everything inside me was coming out. She caught the first few shots in her mouth, I suspect assuming I was done and she raised off me but that was hardly the case. She watched, eyes locked on me with a devilish smirk. I continued to orgasm, shooting a load landing on my chest and another, and yet another, until I had a sticky pool of semen collecting on my check and stomach.
Ashley smiled, finally looking me in the eye and uttered the most beautiful words I have ever heard, “You better like me Greg, I swallowed for me”. She hopped off me and walked to grab a power-ade from the fridge.
I started to feel exposed again, as tried to move but was afraid to get cum all over her comforter and noticing my erection was starting to wither. I asked awkwardly, “Do you have a towel” to which she put on her glasses, opened a cabinet and grabbed a towel. “Here, I got these just for this purpose”.
I chickened out on staying the night with her as we’d surely had sex, fucked, and any other word for it.
Then fast-forward a year or two later. I was finally attending University of Oregon and I hadn’t had a GF since, and I met this girl Jen. I’d later learn she was depressive and would leave me depressed after a failed relationship but this isn’t about that, she’d be the one. Jen was 5’4″ so I stood about 2-3 inches taller than her. She had long straight dark brown hair that below her shoulders, she never wore makeup. She didn’t have her ears pierced. She worse sorta off beat clothing and didn’t show a lot of skin but tended to favor tight sweatshirts to show off her rather large breasts. She had blue eyes with rather defined orange highlights circling her pupils, rounded soft features, and when she’d fix herself up would draw attention from most red blooded males. She was playful but reserved and often painfully quiet.
First date I didn’t even kiss her, second date, I made out with her then again attempted fingering her. I was afraid Jen by her lack of fixing herself up wouldn’t “trim” herself but to my good fortune she did. When I placed my fingers into her she was damp, moist and warm. She moaned and her cheeks blushed but I didn’t manage to bring it home but I did wipe my dripping fingers on her stomach grinning. I was insanely turned on by her sounds and probably went home that night relieve myself.
Third date, I repeated the same act, but taking her pants off and shirt completely off. Same routine but I couldn’t take it, watching her have all the fun I decided I’d clue her in. She was massaging my crotch through my jeans so instead I placed her hand inside. It worked.It felt great. She stroked and she wrapped around me on her bed. I over emphasized my breathing to let her know that I too was enjoying it. She pulled down my pants and began stroking gently. I can’t say honestly if I enjoyed that handjob more than than my first blowjob. I pulled up my shirt in preparation , and released. It was much more innocent than getting head for the first time. Instead of running off from Ashley, after I had cleaned up we made out more, I sucked on her breasts, and teased her. We both smiled and stared a bit speechless and then talked and joked, and laughed. Jen wasn’t the sex crazed girl Ashley was, but she had her sexual side that she was beginning to embrace.
We’d go out on dates that generally ended up in our usual Indulging in each other’s bodies. I gave her an orgasm, and I was thrilled and became rather skilled with my left hand. We’d make out, get hot, then begin playing with each other, often joking and laughing during our sexual play. We’d get dirty (still avoiding actual full on intercourse) as she used her own feminine power as lubricant to give me a handjob, sometimes the handjob position would be such when it came time to me to finish, I’d end up dousing her across her stomach and chest, and I’d let her indulge in her own fetishes as she’d love to tease me by stroking me until I had a large wet spot either on my jeans or underwear. I tried to talk her into oral sex, “I will if you will” but no such luck. We built our confidence up over the course of 3 months. We both became more bold, as such one handjob ended up with me firing a rather large amount her joking, “Damn boy, maybe you shouldn’t wait for me to this”. We’d prod each other about each of our sexual desires, fantasies and curious questions if either of us were to indulge by ourselves. One such story while were dating, she was feeling frisky before bed and had to get one in before she could sleep. She had early class the next day and ran out the door. In class she put her hand up to her nose and realized what she had done the night before and laughed sheepishly to me. I was all ears, my girlfriend was teasing me.
We both wanted each other, she once tossed me on the bed when I came over the visit and promptly removed her pants, before a basketball once I was some hot for her without even seeing her I asked her to give me a quick one. She rolled her eyes and said, “Boys†as she pulled up her sleeve.
Our sex play became more serious. We’d be totally naked making out, and I would roll over her lovebox and we’d both falir up in excitement.
Honestly I can’t cite my first time I had sex. On that valentine’s day, she and got frisky, namely her. She climbed on top of me as I laid on my bed and began rubbed on me, I could feel the heat from her and was fighting every urge to thrust. She and I grinded, me entering her and her just feeling it out, pausing and laughing like, “Hey what are you up to ?†The innocence was still alive even though we were both post 21 year olds, adults, whom still weren’t done growing up.
This sort of practice continued for a month but Jen’s overriding depression was starting to get the better of the relationship. I didn’t dare force the sex talk and when I finally did she closed up. One of those times we actually crossed the line. I can’t name a place or time, just that it happened. By the time we were at the point of just outright sex, 6 months in she called it quits on me. The innocence was gone and the honeymoon was over.
I let Jen get to me a little too much and I learned my lessons, to which I still reflect on two years later. They’re the type of memories that bring a perk of a smile and a somber gaze of in space. My first time isn’t even a distinct memory; just a hodgepodge of events of our time spend between the sheets.
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And so that was college
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