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esther

Age when it happend: 23
Where it happened: friend's house
Langauge: english
Sex: Female
Rating: 5
Category: Straight

it was with a friend. he was a few years younger than me. i had known him for a few years and he was one of the closest guy friends i ever had. he had liked me and kissed me once, but i didn’t want to be with him. i was a prude up until then. he was my first kiss, too. i was taught that sex is a sacred thing, but had recently decided that waiting for marriage was a ridiculous idea and that i could stand to wait until i was in love. i’ve never been in love.

he was unexperienced. i was his first, too. one night while on the phone, i proposed an idea to have no strings attached non-sex. the rules were simple. everything but sex (intercourse)… i had told him to not let me have sex with him. i was always the recipient. it was a deal that i was quite happy with and he seemed eager to have the opportunity. after several weeks of making out in the car and in public spaces and hand jobs and oral on me, (the most amazing touching and oral ever) he invited me over to a friend’s house that he was house-sitting. we were watching a cheesy movie he had wanted to show me.. i fell asleep during the middle of it. i realized he was trying to create a boyfriend/girlfriend scenario. i thought that maybe it was possible we could hang out and not do anything physical. wrong. i was actually incredibly tired that night from work and staying up late the night before. but we made out anyway. mentally, my brain was almost shut off by the time we got into bed and started undressing, but i was still turned on. the fact that i was holding back made it harder to stop. i got as close as possible to playing with him without letting him inside. i tried to keep my underwear on, but of course eventually it was just getting in the way. so off it came and we were completely naked.

i’m not sure that i was ready. i don’t think people ever are. i was conflicted because here i had waited so long and for just the right someone. and i was jaded because i was almost 24 and i had never even come close to finding that person. i was disappointed because of my unrealistic expectations about the person of who should end up being my first. he was not the one i wanted.

the act itself was also disappointing, especially considering how great everything before it had been (he was basically all my firsts.. first kiss, first everything, all the way).

neither of us knew what it was supposed to feel like. he said he was going to put it in, he took my silence for a yes, so he went ahead and pushed. i was tired and my mind was thinking “i don’t feel … anything. God, is it supposed to be like this? why do people like this?” i immediately decided he must be too small for me, but had no one to compare him to, so i just lay there waiting for him to finish. this new movement was awkward and i just wanted it to be over. for some reason he didn’t come and i was sad about that. i wanted to know why, but i wasn’t about to try THAT again.

i had previously tossed around the idea of sleeping with him and being his girlfriend, but never actually decided to. and then, it was just happening. it wasn’t until that moment when he was inside me that i was certain that i didn’t want him there and that i didn’t want to be with him.

that was the last time we did anything. after that he kept asking me to be his girlfriend and i kept saying no, and eventually i stopped talking to him altogether. to this day, i cannot be in the same room as him when we are with mutual friends.

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