Straight Female / 37
I have never been what is considered attractive, I dress well but know that I am not particularly feminine and don't possess what men want. My friendships have been with women, but never sexual. My best friend, who like me has never dated, vacation together and we have been on many trips and cruises together. To save on expenses we shared rooms, and eventually decided to just live together.
On our cruise to the Adriatic, I met a man in line and he started a conversation. He was from Boston, recently a widower, and getting away from it all. In the dining room I asked him to join us and we struck up a friendship. The three of us spent the shore tours together and took all our meals together. He asked me if we were together, as in a lesbian relationship, and I told him no, we were just good friends.
On the last night on deck, before sailing into our last port he kissed me and told me quite frankly, without any ceremony that he had been 'without' for some time and if I would do him the favor of having sex with him. It was as matter of fact as you can get, just go with him and have sex.
As matter of fact as it was, I felt something and agreed. We went to his state room and he got undressed and told me to get undressed, I asked him to turn off the lights, but he insisted on keeping them on. He was naked standing in front of me asking me to undress, to get naked.
It was hard to undress, to take my bra off in front of him, to take my panties off in front of him. It was my first time, my very first time in my whole life standing naked in front of a man who was going to fuck me for my first time. He stood and looked at me for a long time before he asked me to sit on the bed and give him oral sex to help him gain an erection. He told me he had taken his pill but it required me to encourage him, to give him oral.
The lights were all on, I was naked sitting on a bed and this man had his penis in my face and I was supposed to put it in my mouth. He put his penis against my lips, and I looked up at him, I am sure I was begging to not do it, but he just said 'suck'.
I tried, he grabbed me by the hair and kept telling me to suck, to finger myself so that I would get wet, he was grabbing my hair and moving my head and thrusting his penis in my mouth, he did get an erection but not because I sucked him. He stopped and took another pill and told me that I had to suck him, to suck him and suck out all of his cum. He held my chin hard and put his penis back in my mouth and told me to suck.
He got very hard and pushed my head back so I fell back on the bed and he told me to spread them, he took my knees and spread open my legs and he put two fingers in my vagina and asked me if I wanted him to eat my pussy. It was about then that he realized that I had never been with a man before, he leaned down on me and pushed his fingers deep into me and told me that I was going to get fucked and he liked hot pussy, he didn't like a woman who held back, he wanted hot pussy.
He fucked me, he got on me and fucked me, he fucked me for a while and told me to move my hips, to get in rhythm, but I couldn't, I was so self conscious. After a while, he got off and told me to turn over and he was going to doggy fuck me and for me to play with my clit. Putting myself in that position was not easy at all, he opened me and stuck his penis in me and started to fuck me telling me to rub my clitoris with while he fucked me. He was very angry by then, I wasn't doing a very good job and he was getting angry and frustrated with me.
He grabbed me by the neck and pushed my head down into the pillow and told me to rub my clitoris until I had an orgasm. I tried, but failed, I just couldn't get aroused. He was still fully erect, I could feel how hard he was, he turned me over again and put his penis back in my mouth and told me to suck the cum out of him. This time I sucked, I really sucked hard, and he held my head and shoved himself in and then pulled out enough for me to suck him again. He pushed me back down on the bed and opened my legs again and sucked on my clitoris while he fingered me and then got on top of me on more time and fucked me until he came.
My first time was a disaster. He asked me to stay with him, I knew my friend was waiting, so we called her and told her I was going to stay with him that night. Early in the morning he got an erection again and this time he fucked me more gently and then he asked me if I wanted to try anal, because if it was my first time, I might as well do it all. I let him do what he wanted. I just shut my eyes while he penetrated me, it felt good, real good, it felt so good, I just breathed and enjoyed while he fucked me. It was so unexpectedly good, of the whole night this was good.
When we parted he kissed me. My friend asked me over and over again what we did, I told her we had sex, but I did not tell her about the early morning. I told her about having to suck him, and about him getting angry and frustrated with me, but I did not tell her about the early morning sex, I keep that for me. I wonder what he tells his friends about his cruise.
On our cruise to the Adriatic, I met a man in line and he started a conversation. He was from Boston, recently a widower, and getting away from it all. In the dining room I asked him to join us and we struck up a friendship. The three of us spent the shore tours together and took all our meals together. He asked me if we were together, as in a lesbian relationship, and I told him no, we were just good friends.
On the last night on deck, before sailing into our last port he kissed me and told me quite frankly, without any ceremony that he had been 'without' for some time and if I would do him the favor of having sex with him. It was as matter of fact as you can get, just go with him and have sex.
As matter of fact as it was, I felt something and agreed. We went to his state room and he got undressed and told me to get undressed, I asked him to turn off the lights, but he insisted on keeping them on. He was naked standing in front of me asking me to undress, to get naked.
It was hard to undress, to take my bra off in front of him, to take my panties off in front of him. It was my first time, my very first time in my whole life standing naked in front of a man who was going to fuck me for my first time. He stood and looked at me for a long time before he asked me to sit on the bed and give him oral sex to help him gain an erection. He told me he had taken his pill but it required me to encourage him, to give him oral.
The lights were all on, I was naked sitting on a bed and this man had his penis in my face and I was supposed to put it in my mouth. He put his penis against my lips, and I looked up at him, I am sure I was begging to not do it, but he just said 'suck'.
I tried, he grabbed me by the hair and kept telling me to suck, to finger myself so that I would get wet, he was grabbing my hair and moving my head and thrusting his penis in my mouth, he did get an erection but not because I sucked him. He stopped and took another pill and told me that I had to suck him, to suck him and suck out all of his cum. He held my chin hard and put his penis back in my mouth and told me to suck.
He got very hard and pushed my head back so I fell back on the bed and he told me to spread them, he took my knees and spread open my legs and he put two fingers in my vagina and asked me if I wanted him to eat my pussy. It was about then that he realized that I had never been with a man before, he leaned down on me and pushed his fingers deep into me and told me that I was going to get fucked and he liked hot pussy, he didn't like a woman who held back, he wanted hot pussy.
He fucked me, he got on me and fucked me, he fucked me for a while and told me to move my hips, to get in rhythm, but I couldn't, I was so self conscious. After a while, he got off and told me to turn over and he was going to doggy fuck me and for me to play with my clit. Putting myself in that position was not easy at all, he opened me and stuck his penis in me and started to fuck me telling me to rub my clitoris with while he fucked me. He was very angry by then, I wasn't doing a very good job and he was getting angry and frustrated with me.
He grabbed me by the neck and pushed my head down into the pillow and told me to rub my clitoris until I had an orgasm. I tried, but failed, I just couldn't get aroused. He was still fully erect, I could feel how hard he was, he turned me over again and put his penis back in my mouth and told me to suck the cum out of him. This time I sucked, I really sucked hard, and he held my head and shoved himself in and then pulled out enough for me to suck him again. He pushed me back down on the bed and opened my legs again and sucked on my clitoris while he fingered me and then got on top of me on more time and fucked me until he came.
My first time was a disaster. He asked me to stay with him, I knew my friend was waiting, so we called her and told her I was going to stay with him that night. Early in the morning he got an erection again and this time he fucked me more gently and then he asked me if I wanted to try anal, because if it was my first time, I might as well do it all. I let him do what he wanted. I just shut my eyes while he penetrated me, it felt good, real good, it felt so good, I just breathed and enjoyed while he fucked me. It was so unexpectedly good, of the whole night this was good.
When we parted he kissed me. My friend asked me over and over again what we did, I told her we had sex, but I did not tell her about the early morning. I told her about having to suck him, and about him getting angry and frustrated with me, but I did not tell her about the early morning sex, I keep that for me. I wonder what he tells his friends about his cruise.
