Post # 107
Let me preface this by saying that I’m bisexual and have dated mostly women.
My first time with a woman (age 19): glorious.
My first time with a man (age 20): awkward. I’m talking can’t get it in, having to switch positions five hundred times to find one that wasn’t excruciating for me, and me constantly reaching for boobs that weren’t there.
I’m 26 now, and man-sex has gotten a lot better 🙂
Post # 108
I lost my virginity on prom night. I was 16, he was 17, and my prom date who I had met maybe three weeks prior when my friends set me up with him. Total cliche, I know I know.
It wasn’t horrible and it wasn’t wonderful, more awkward than anything. It didn’t help matters that we were at his friend’s house in his friend’s bedroom, which granted was about the size of a living room, but still awkward to have his friend sitting on the other side of the room playing a video game. It lasted maybe five minutes, and only because a friend of mine who had tagged along with her prom date came bursting in saying that we needed to go before her parents woke up.
Thank the lord he wore a condom, because a couple of weeks later I found out that he’d been sleeping around with a girl who had chlamydia. I went to a free clinic and got tested anyways, and thanked my lucky stars. I didn’t see this guy again until about three years after the fact when I was going through kind of a whore-ish phase. Let’s just say I like to pretend those six months didn’t happen.
Post # 109
I was 17, a month shy of 18. We were both virgins. It was romantic! He lit candles that I had bought him for his birthday. He was going so slow and gauging my facial reaction to see if it hurt (it did not). Then we spent the rest of the day going at it like bunnies. He was the first of his friends to do it and we hung out with them later in the day and they were congratulating him and winking at me. ha. I was very sore!
Post # 110
I was 16, my boyfriend was 18. I was a virgin and he was not. His parents were divorced and his mom was re-married. His dad traveled alot and he had a key to his dads townhouse. My Boyfriend or Best Friend had a “loft style” bedroom in his dads townhouse. The summer between my sophmore and junior year in high school we “hung out” there many days. “Hanging out” actually translated into making out and oral sex.
It was summer day and we were both off from our part-time jobs, so we went to his dads to “hang out”…We watched TV, made out, had oral sex, went swimming at the home owners associations pool, and went back and had lunch at his dads.
While watching a movie that afternoon the making out started again. My Boyfriend or Best Friend had NEVER pressured me. That day he asked “when do you think you want to try something more?”…after making out some morre I asked him if he had any condoms….and he affirmed that he did. After some more make out, I told him “today is the day”.
We went off to is loft bedroom and as we made out he serched his bedside drawers for condoms….and could not find them. He was very respectful and sweet, and kept apologizing. I was SO HORNY and had made my mind up that I wanted to do this…so I stupidly made him promise that he would not get me pregnant!!!
He was sweet and took his time, there was a heavy pressure but no sharp pain. I did not have an orgasm and we only had missionary sex before he pulled out.
That was a Thursday. His dad was home Friday thru Monday, and left to go out of town for work on Tuesday. It was a long 4 days for me…I wanted MORE!! Tuesday afternoon I called in sick at JCPENNEY and my Boyfriend or Best Friend called in sick at his job so we could go to his dads place….and he definetly had condoms!!
Post # 111
Nothing good, my first was just bad and ugly!!!!!!!!!!!!!!
It was the day after my 17th birthday, with my second boyfreind of high school. He was also 17 and not a virgin.
We were at my best friends house and her parents were away. Her boyfriend came over and so did mine. We hung out all day and grilled (burned) some burgers.
After a failed attempt at cooking my friend and her Boyfriend or Best Friend went off to her room, leaving me and my Boyfriend or Best Friend alone in the living room. He had been asking me almost ever day about having sex…so that night I decided “why not”.
He went to his car to get a condom and I went to the guest room and slipped under the covers. Ten minutes later it was all over, he had cummed and turned the TV on…
Two weeks later he broke up with me, we only had sex one other time.