When I was growing up, I lived outside a real small town. Our high school had 240 students in grades 9-12. And it was the kind of town where, to fit in, you either had to be super good looking, or your family had to have been there for about a hundred years. I didn't meet either of these qualifications. And to make it worse, I don't like most team sports. See, in a high school of that size, nobody gets cut from a team. If you want to play football, you get to be on the team. You might not play a lot ... but you get to be on the team. Same with basketball, or wrestling ... So, if you aren't ON any of those teams, it's only because you don't want to be. And that, in small town thinking, means you think you're better than they are.
Now, if that same kid is able to get good grades without studying, and is say, 20 lbs overweight, well ... you can see that his life is going to basically suck. Add all that up and you have a recipe for ... ME! Basically, I was the chubby nerd. I had a few friends, but I wasn't popular. And if I was even SEEN talking to a girl, the crap I would get from the 'cool kids' was out of control. It wasn't even worth it to try, after a while. And so, upon graduating from high school, I was not only a virgin ... I hadn't even ever been on a date!
So, I go away to college, and basically that's when my life started to become worth living. I had a LOT of friends ... I was actually pretty popular ... and I had a blast. I wasn't a very good student, though, because I had never had to study before. I had very poor study habits, and even got suspended for bad grades once ... but I persevered, and eventually got my degree. And along the way, I had a VERY good time.
However, I never learned much about women! Oh, I eventually got laid ... It was my second year, and I met a girl I really adored. I followed her around like a puppy until she eventually caved in and started dating me. We had a great relationship, and the sex was fantastic. Pleasing her was important to me, and I soon found out that making my partner feel good made ME feel good. Anyway, she and I were together for 4 years, and probably would still be today ... but she was a great student, and graduated two full years before me. We didn't survive the distance thing ... she eventually met someone else and dumped me! I took it pretty hard, and I was inconsolable for months. Somehow, during that time I managed to find my way into bed with 4 or 5 girls, but each time it was a situation where the chick came on to me! If I'd had to approach them, I'd never have gotten laid, because I was still destroyed over my breakup. But, eventually, I got involved with another girl that I was with for a year and a half or so. She was very pretty, sexy, and always ready to fuck. She was also a compulsive liar and a cheater, but I didn't find that out for quite a while. I liked her, and I loved the sex, but I didn't love her. And when I found out that she was screwing around, I dumped her. I wasn't really too upset about this breakup ... mostly because I was never that serious about her. But regardless, I was single again.
Now, you have to realize that by this time, I am 24 or 25 years old. And while I've had a TON of sex, I've never actually 'picked up' a girl before. I met my first girlfriend just before she broke up with a friend of mine, so we were friends first (it CAN work, I guess). The second girlfriend, and the quickies in between, approached me! So, basically, I have ZERO skills in picking up women. And to be honest, I was too scared to try, unless I had a few drinks in me. The next few years were pretty lonely ... me, some hand lotion, and rosy palm ... It's pretty pathetic, but during the next 4 or 5 years, I think I screwed a grand total of 5 women. And I have no idea how I ever accomplished that.
By the time I turned 30, I was determined to turn my life around. And I started by getting in shape. I spent 6 months lifting weights and riding a mountain bike, all while on a super restricted diet. If there is one thing I can say about myself, it's that when I'm set on a goal, I'm like a locomotive ... There is no stopping me. So, by the end of 6 months, I was lean, in great shape, and I guess, kind of good looking. I still had no confidence with women ... but that was about to change.
It was about that time that I went on a trip with some of my college buddies to Cancun. And while we were there, I loosened up a few of my rules ... for one, I allowed myself to drink. I had never been a heavy drinker, and while I was losing weight, I didn't allow myself ANY alcohol. So, at this point, I could get pretty buzzed off of just a couple drinks. It was during this trip that I developed my fondness for a good margarita! The other thing I was determined to address was my awkwardness with women! I figured, hey ... I'm never going to see any of these chicks again ... so who cares if they laugh at me, or think I'm a nerd. And I was convinced that they WOULD laugh ... I just didn't care anymore. I had been jerking off twice a day for 5 years, and I was really tired of it! I figured if I threw enough shit at the wall, eventually some of it would stick!
Well, the first night out, I had about 5 margaritas ... and that left me so drunk that I couldn't even speak ... but on the second night, I had it all figured out. I gulped down two margaritas to get my courage up, and then started looking for a chick to approach. Luckily, there were plenty there.
I spotted this girl across the room with two others. The girl I saw looked to be about 25 years old, though her friends looked a little older. While they were laughing and drinking and having a great time, the girl I was looking at didn't seem to be ... It looked to me like she was looking for someone in particular, and I figured she probably had a guy somewhere who just hadn't showed up yet. I moved on.
After chatting with two or three other girls, I had seen some prospects that I was interested in, but none seemed to really connect with me ... I figured I just needed some more courage, so I had another margarita and resumed my search. At one point, I excused myself from my friends to go to the restroom, and I bumped into the girl I'd been watching earlier. She was very pretty, and from close up her eyes were captivating. She could stand to lose about 15 lbs, but it didn't detract from her a bit. And I, especially, wasn't one to complain about being a little too heavy. I guess it was pretty obvious that I was thinking dirty thoughts as I stared at her, because she blushed a deep red. We introduced ourselves and she told me her name was Jenny. I had forgotten about pissing ... at that point, I could have held a swimming pool full of margaritas ... I decided I was going after this woman, right then. I asked her to let me buy her a drink, and she accepted. So, we got two more margaritas. I remembered that 5 was enough to ruin me the previous night, and I'd already had three, so I just sipped mine. She went through hers pretty quickly and I got her another.
As we were talking, she told me a little about herself. She was a grade-school teacher, as were her friends. There were supposed to be 4 of them, but one of them was unable to make her flight. They were expecting her to catch up to them the next day. Jenny, however, was pretty bummed, because the missing friend was actually HER best friend, and she didn't really know the other two girls all that well. So, that explained to me why she didn't look very comfortable earlier. She was looking much more so now, after a couple drinks.
I asked her where they were staying, and it turned out they were in the resort next to ours. She told me the room they had was incredible, with a great view of the ocean, and she hoped her friend would get there to enjoy it ... She said she felt bad because the other two had a room on the other side, and their view sucked.
At this point, the little devil-guy that we all have inside us finally made his appearance! Finally! It only took the little fucker 30 years, but at least he was here now, and I listened to what he had to say! He told me to capitalize on her being alone in her room! So I did ... I told her that for safety reasons, I had probably better accompany her back to her room, and make sure no one was hiding in it! She laughed, but she blushed again, and said that it was probably a good idea. I also told her that if she wanted, I'd be willing to stay with her, since that big empty room was bound to get lonely!
Well, I don't know what it was ... the corny lines or the drinks, or maybe she was just as horny as I was, but the next thing I know we're back at her room. We started out on the balcony, and I spent several minutes kissing her. It felt good just to hold someone ... it had been a long time since I'd been able to do that. But she was a GREAT kisser, and her lips were full and soft! I was happy enough doing that, but I wanted more, too.
Her breasts were awesome. Maybe partly because she had a few extra pounds, like I said. But these tits were big, and pretty firm, and they had nipples that stood out proud, probably half an inch. We were still on the balcony when I got them out and I sucked her nipples under the moonlight until we just couldn't stand it anymore.
We went back inside, and sat on the sofa ... and she started to get second thoughts ... I could tell she had become apprehensive, and I asked her what was the matter. She told me it was a couple things ... first, she'd never done the one-night-stand thing before. She told me that she was struggling to convince herself that fucking me wouldn't make her a slut! Well, I was a little disappointed, at this point, because I thought that we were probably all done. But she went on, telling me that on the other hand, she was super horny, and thought I was probably the hottest guy that had ever been interested in her. Well, I wanted to fuck, of that there wasn't any question! But, I'm not an asshole ... and I don't let my cock think for me. I told her, and I meant it, that if she wanted to stop now, or at any time, all she had to do was say so. I didn't want her to do anything she didn't want to do! I lightened the mood by telling her that if I were only allowed to continue to play with her beautiful breasts, I'd be fully satisfied. But what probably saved the day was when I jokingly told her that doing so would probably cause me to cum in my shorts! She laughed and asked why, and I told her that she was beautiful ... I was very attracted to her, and it had been a very long time since I'd been with a woman. I told her that I couldn't guarantee that she wouldn't cause me to have an accident, even if all we did was continue as we were.
She blushed again, and told me that just in case, I'd better take off my shorts in order to prevent soiling them by accident. I told her that I'd be too embarrassed to be the only naked one, and she laughed at me as she removed the rest of her clothing, too.
SO, we're naked. We're still on the sofa, and we're petting pretty heavily. I'm kissing her perfect lips, and sucking on her world class nipples, and then I ask her to move to the bed. And again, she hesitates!
This time, she's got a more practical issue ... and one neither of us had thought about ... pregnancy! Jenny told me that she wasn't on the pill, since she didn't have a boyfriend. And the thought of buying condoms never crossed my mind! Some super-lothario I am, I thought. And we both were obviously disappointed. But then I told her that I was fine with that ... if she was willing, I figured there were a bunch of other ways to please each other. And I guess she wasn't as experienced as me, because when she finally figured out I was going to go down on her, her eyes got about twice as big as normal.
Her pussy tasted wonderful. It was sweet, and wet, and her clit was a small but pronounced little bump at the top of her soft pussy lips. As I held her clit between my lips and gently slid my tongue back and forth across it, I could swear I felt her heartbeat through it. She went wild, and I lost contact several times as she thrashed against me. She must have come 3 or 4 times, her pussy getting wetter each time. Then I asked her to roll over onto her stomach. She got a weird look on her face, but she did it.