B and I went on our first date as teenagers. I was an eighteen-year-old high school senior, and she was a nineteen-year-old college freshman. It was my senior prom, and I was the only guy there who was able to score a date with a college girl.
I treated B like a gentleman should. Bought her a beautiful corsage that matched the dress, took her out to a lovely dinner, and made sure to show her off to all my friends and teammates. After leaving the prom, I took her to a movie before dropping her off at home. I must have made quite an impression since she called me again soon after, and we arranged a follow-up date. Thank God she did that otherwise, we would not be married today.
Fast forward several months, and we are now seeing each other regularly, three or more times a week at least. I am now a college freshman, and B is a sophomore, but we are attending separate schools and still living with our parents. This was the only serious relationship either one of us had ever been in, so everything progressed quite slowly compared to more experienced couples. We eventually shared our first kiss, and that led to some heavy make-out sessions. These left me with blue balls and led to some very focused masturbation sessions.
While making out on the couch one afternoon, I decided to do something new. I slid my hand down the back of her jeans and grabbed her ass. I was so nervous she would tell me to stop, but when she didn’t, my impulsive and adventurous side took over. I went wild exploring her body, grabbing handfuls of her luscious ass, then sliding my hands up her shirt and feeling her breasts for the first time. It was something I dreamed about for years, feeling a beautiful woman’s breasts and bare ass. I no longer had to imagine what they would feel like. I did resist the urge to go down the front of her pants at that point; it just seemed like one step too far. There was also the fact that my parents and younger brother could have walked in at any moment, so we had to keep this as PG-13 as we could.
As I walked B out to her car that night, she whispered to me, ”I can’t believe I let you feel me up like that, you naughty boy.”
“I just couldn’t resist anymore. You didn’t seem to mind, “ I replied.
“It did feel pretty good. See you tomorrow, right?”
“Yeah, we have preseason conditioning until 6, but I can come by your place for dinner afterward.”
We kissed, she left, and I went to my room to release my sexual tension.
Fast forward a few more weeks, and I now have a television in my room. This was a major game changer. We now could spend all our time at my parent's house in my room instead of the living room. Even though we were both adults attending college, we still felt the need to hide our make-out sessions from our parents. It wasn’t long before B was straddling me cowgirl style. I pulled her shirt up so her tits could hang out. She started dry-humping me, grinding her denim-covered pussy across my rock-hard erection, which was easy for her to feel through my athletic shorts.
I stuck my tongue down B’s throat, and she reciprocated. I squeezed her tits before licking them for the first time. B moaned in ecstasy and then whispered, “Oh wow,” as she intensified her hip grinding.
This had me building towards an orgasm. I didn’t know what to do. I had only ever orgasmed while masturbating, and I didn’t know if I should say something, thus risking an end to our rendezvous, or continue and eventually cum in my shorts.
I chose the latter. I grabbed B’s ass with one hand, one of her boobs with the other, and kissed her as deeply as I could. She kept the pressure on my cock, and I exploded, gushing an enormous amount of cum into my shorts. I didn’t mention that I had just cum because I was embarrassed and didn’t know how she would react. Since B seemed to still be enjoying herself, I acted as if nothing had happened. We continued to grind away at each other until she buried her face in my shoulder to stifle her cries as she, too, had an orgasm.
“Wow, that was amazing,” I said.
B agreed, then looked down at the giant wet spot on her jeans. “I must have leaked through my pants,” she said.
“Well,” I added, “that could be from me. I came in my shorts; some of it must have soaked through to your pants.”
"Really?" B replied, "I wasn't the only one then. Have you ever done that in your pants before today?"
"No, this is the first time. I'm going to need to change."
B climbed off me, pulled her shirt back down to cover her lovely tits, and began fixing her hair. I got up, grabbed some clean clothes, and went to the bathroom to change. I returned with a hand towel for her to attempt to wipe some of our combined fluids from her pants. It didn’t work too well. She decided to just wait with me a while longer until she was dry enough to not be noticed when we walked out. These were the first orgasms we had given to each other, and the first either of us had that didn’t involve masturbation.
The dry humping stage lasted a couple of weeks, it was new, and felt amazing to have another person make me cum, but I wanted more. It wasn’t long before we were back in my bedroom, and I made the next move, putting my hand down the front of her pants and feeling her pussy for the first time. I was confident this time, knowing she wanted it and wouldn’t ask me to stop. It was hairy, soaking wet, and everything I dreamed it would be. I was now able to enjoy her whole body with my hands. She responded by reaching down my shorts and finally taking my hard cock into her hands. I pulled my shorts down and let my manhood out so she could more easily access it. Releasing my cock would also allow me to cum without the need to change my clothes afterward.