Where it happened: Hotel
Langauge: english
Sex: Female
Rating: 4
Category: Straight
So I have the most comedic first time that i’ve heard or read by far. I’m 19 and after a long time of shutting myself off from people, never giving guys a chance; I decided to lose my virginity to a close friend. He was someone I trust, and he was also a virgin, so i decided it was mutual gain. My friend was (not to be shallow or conceited) out of my league look wise, but was a good overall friend (not bad looking). He was always over-sexual, his nickname is creepy so that should give you an overall idea, we really habitually call him creepy. It was probably more to him than me, but i had a hurdle i felt i needed to get over and could not with some random person. This had to be with someone whom i know respects me and knows how special this is seeing first hand how particular i am. I told him exactly what the deal was and how i did not want anything romantic cause i did not feel that way for him. I felt i choose being comfortable and being respected overbeing inlove and sexually attracted. He down played his feelings for me to feel comfortable about going through with this knowing i get uncomfortable with intimacy. *probably why i was forced to settle at this point* He had tried to have sex and failed to close the deal with a second choice; and I also decided against having sex with another friend because of his deeper feelings for me. So the next logical choice would be each other. The day came and i was in town and was staying at a hotel. I drunk a few beers and he consumed only 1. So he had problem getting an erection, so i offered a back massage, he agreed. He still could not get an erection. When he went to get up he threw himself off the bed catching his earring and producing blood. We laughed it off, it was no more embarrassing then not being able to get an erection. He ask to excuse himself so he could go try by himself in the bathroom, i allowed him too. Of course laughing to myself at this point. He came out and said he was ready i placed the condom on the semi-erect penis not knowing the difference. He tried to kiss me which we already discussed was not going to happen and was not part of this arrangement. He further insisted. I kindly declined while trying to help him maintain somewhat of an erection. I then got on top and lowered myself on to it. For 15 seconds it was hard enough for the head to just penetrate and i was in pain, until all of a sudden i felt nothing at all, no pain, no sensation, no feeling what-so-ever. I asked if it was in he looked at me distress and said yes, after another couple seconds he slipped out. I knew something was wrong. I got off knowing 1. Condoms are supposed to be on fully erect penis and could slip off 2. I was no longer into it. He rubbed himself while he pleaded with me to give him another shot, his strokes quickly became more vigorous. It became a struggle, not laughing especially with my talk first think later attitude. He held his hand out and continued to beg while he rubbed himself, making me feel extremely uncomfortable and overwhelmingly amused. I told him it’s not hard enough, I’m to tight, the condom starting to slip off; and due to the following your just going to have to help yourself……later i should of said. He sat there molested himself for 30 more seconds while akwardly looking at me and climaxed violently into the condom. Once he begin to come to his senses i was laughing at his facial expression. I saw him start to regain emotions the most present ones shame and humiliation. I tried to say somethings to make him feel better, but i was kind of disgusted. This showed as i talked and then laughed. Remembering his eyes wide and mouth gaping open while he pawed at himself naked in bed, begging, ready to climax. Yet couldn’t maintain a erection through penetration. I probably would of been more sensitive if he didn’t just bust a nut right in front of me while begging me to try again with him. But he did and i felt disrespected, so I made a point to joke on him. He was mortified. He been obsessed with me sense he met me, trying and pleading to get in this situation and when he does he can’t even perform. The situation was known throughout our circle of friends he got teased relentlessly for it, especially the continuing to masturbate part. I guess this count as my first time, extremely disappointed but oh well. At the end of the day he’s my friend and i care about him. So as long as that doesn’t change, I’m satisfied….i guess.
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