Straight Male / 52
The first time can never be forgotten. For me, it was when I was 14 and invited over to a girl's house that I was really sweet on, I'll call her Sandra Dee. I was elated that the sweet, cute Olivia Newton-John type girl called me and invited me over. When I got there it turned out I was invited over to take turns pulling a private train on her. I was in the living room with four other boys. I only knew her younger brother, I'll call Don, so I mostly talked to him. Since it was his house too, he was playing host.
At first I didn't want to be there. I liked to think of her as virginal. She looks and acts sweet and innocent normally, much like Sandra Dee. We watched tv, talked and waisted time until we were told by the boy coming out, whose turn was next. I was the last there so I was to be last. The first boy who finished didn't stick around much. He did stick around long enough to boast and tease that we were having his sloppy seconds. The other boys reminded him that he wasn't first tonight either. I wondered how many before him.
I was really conflicted. This was shattering my image of her. I was a virgin and had thought she was too. I learned this wasn't the first time here for half of them in the room. The only other boy that was invited for the first time was two years younger than me. I doubted if his equipment even worked yet. After two boys left it was just her brother and me as we waited for the other new guy to take his turn.
I was really mixed about this and admitted it to him. I asked him how long this as been going on. It started with their older sisters doing stuff like this. Now that she got involved Sandra Dee is taking it to a new level. I asked him if he ever took a turn. He blushed and looked down but admitted, he does. I coaxed out more. Part of the deal is if he plays a good host, he gets to go last, after all of the other boys had gone home. This sister is the only woman he's ever been with. I had to give him a break on that as he was only 12. Aside from that, she'll sometimes use him when an unrelated boy isn't handy enough. He was clearly conflicted about it too. He knew it was wrong but he was whipped.
The boy taking his first turn was his classmate. It is part of his role to find boys for her. She finds them on her own mostly, but she especially loves virgin boys and grown men. He helps finding virgins. He asked if I was upset that he invited me. He wasn't the one who called me, so at first I was confused. I then got that it was him that suggested me and gave her my phone number.
I asked what kind of boys got invited back. He didn't completely know all but he knew she liked the sweet ones that loved to eat her out but also the brutish ones that were jerks, strong, rough and basically r**ed her. She is obedient to them but bossy to the nice ones.
Although we were the same age, I was shorter and smaller than her most of our lives. Only now I was her equal. I was no equal to the two larger boys that already left. I was no bully anyways. I was going to have to be sweet. Eat her out. I didn't know what that really entailed but I was willing. All of these other guys wanted to use her. Even at 14, I wanted to marry her.
When the younger boy came out he was ecstatic and boastful. Having chatted with the brother, I felt like this might be his last time invited over. She called in her brother for a moment. He came out and told me she needed a few minutes to be ready for me. I wasn't surprised. She had done that, at lest somewhat, for each of the last two boys.
I wasn't sure what to expect, but my heart was in my throat and I felt shivers all over. I was nervous. Hi I greeted her. This was my first time having a one on one conversation with her. My brother tell me your a virgin. Oh crap, I think. I wonder what all he told her about me. Come on, she says as she led me to her bed.
She was dressed in a purple silky nightgown and nothing else. I didn't know why she put that on. We were going to be naked soon. She was just as soft, gentle and sweet and both speech and deed as I've seen her before. My mind was still being blown. She wasn't acting slutty at all.
I was a jumble of mixed emotions and clueless. She was a perfect first kiss. When she kissed me my eyes rolled back and I blacked out a second or so. I was in heaven. Each time she kissed me my lights went out. I still don't know what she does, but to this day, no other woman can make me black out just by kissing me. She ALWAYS could.
I looked and smelled all over her body and could not sense a trace of use on her. I was certain she had showered between boys, or at least before me. I was putty in her hands. When she guided me to her pussy I obeyed. She had to talk me through it. I was really clueless. I didn't know what she was supposed to taste like. I could be licking semen. I didn't care. I loved every moment.
I couldn't seem to get enough nectar out of her. I really didn't understand the biological aspects of all of this but I felt I could eat her out of her forever. Right then I was addicted to eating pussy. Not then, but several other times, I've found I can orgasm just from eating good pussy. After a time she got excited and stopped me.
She pushed me onto my back and started to lick and suck on my penis. My brain was on sensory overload. Each touch was super powerful to me. Only now I learned why ALL men love BJ's. She didn't finish me but suddenly moved up and mounted me.
I was again in Heaven. She rocked on me until she said her legs were cramping. She got me to get on top. It took a while to figure out what I was doing. I was in Heaven again. I wanted this NEVER to stop. I wanted to someday die while doing this. I was hooked.
I kissed and messed with her little tits. She asked about how she like them. I told her I didn't know. They were perfect. They were my first real tits. What I didn't say was that they were incredibly small. My sister is 2 years younger than us but her breasts are several times bigger.
When I came I said to myself that I was finally not a virgin and I lost it with the most beautiful and awesome woman on the planet. I didn't care if she was ever faithful to me. I was going to be faithful to her if she'd have me and marry me. I just had to stick around long enough to outlast the other suiters and win her heart. When I pulled out I was surprised to see a condom on. I had no idea how it got there. I didn't own one.
When I left her room the world was changed. I bumped into walls and walked with less control. During my walk home a group of men saw me and one told the others that he bet I just lost my virginity. I turned to them and asked how he knew. He said, Because you LOOK like it. He must be right. I wondered what I looked like as I walked the rest of the way home.
When I later met her brother, I told him that I'd like to be invited back as often as possible. I'd play any part, that I loved her and wanted to marry her someday. He replied, except for the last two parts I sounded like most other boys after their first time with her. Even though that didn't make too much sense to me but I took it as a compliment. Just tell me what I need to do or say to win her heart. He smiled and said he'd see.
As I got invited to more parties with her I got to know her more. I discovered, as sweet as she is, she is REALLY bossy. Even when we played gangr**e on her, she was clearly in charge. She set time, date and time, picked the boys, set the limits, gave the code words and decided when it was over. Fake gang r**e on herself was her favorite fantasy play. Pulling trains seemed to be her most common sexual activity. At least that was what I was invited to the most. Over time, I risked being more wild than the other boys to stand out to her more. It worked, I caught her approval. She gave me my own code word. In the far future, if I r**ed her without her knowing it was me, I was to say my code word just before I leave, so she's know not to call the police.
Most mixed gender times were actually naughty parties of a more party sort. Light drinking, strip poker, Truth or dare, 7 minutes in heaven, guess the tit/boner/pussy and such. She loved to invite boy-girl sibling pairs. Whenever a sibling pair was present she made certain to get them to mess around. The first time was ALWAYS without their knowledge. This usually took place as a glory hole of sorts. The guy or girl has to guess who is on the other side, servicing him, or being serviced by her.
When I found out my younger sister got invited to the same party as me, at this girl's house I knew what was up. I had plenty of time to talk my sister out of it, to warn her, prepare her or simply refuse to go myself. I didn't try any of that. By the time we were both invited I was eager. Brother-sister pairs are more often guests of her parties and I knew why.
My sister proved to be a good sport about being pranked into blowing me. On our walk home I told her the truth about how common it was. I told her about the brother and that was the known part of why. She asked me why I went though with it if I knew what was going to happen. I told her the full truth and pleaded with her to be cool with it all. I really wanted more time with Sandra Dee. My sister's help was key.
I got invited VERY often, with my sister, for a few years. My sister wasn't immune to Sandra Dee's charms and was gay for her really quickly. She claimed she wasn't into women, but my sister was hot for the same girl I was hot for. For one summer, Sandra Dee, was the girlfriend to both my sister and I. I was filled with jealousy whenever my sister had her to herself. My sister felt the same way when I had her alone.
My first FMF and only adolescent threesomes were with her and my sister. Anything I did with Sandra Dee, Sandra Dee made certain I did the same with my sister too. Sandra Dee loved those session and soon so did we. Sandra Dee never knew it, but we began to mess around when home alone. I never had a normal FMF again until I was 22. Not as often we swapped with her and her brother. While I liked that more, it was threesomes more than foursomes with her. During this time Sandra Dee was my girlfriend and my sister was his first girlfriend, officially.
As our relationship with her petered, on her part, my sister and I got closer. For just short of a year, my sister and I were essentially boyfriend and girlfriend as we both rebounded from being dumped by Sandra Dee. It wasn't ideal, obviously, but it was what we both needed. During this time we both got WAY better at our oral sex skills. I think my sister showed the most improvement.
Sandra Dee, never liked me the way I loved her. I still am Facebook friends with her. We've addended each other's sibling's weddings. She is married to a great guy who was clueless about her past when they got married. I don't know the details, but they adopted all of their children. She is still really bossy and so I'm thankful that I never got my wish to marry her. Still beautiful, I still think of her fondly. She has a great life and family.
As for my sister, we tapered off as we started dating others. Even though my sister is younger, she was more desirable so she got way more dates than me. At the end I was the one trying to keep our unique relationship going. She instead started fixing me up with her friends. That was decades ago. We still share sly grins at family gatherings.
I still know that code word Sandra Dee assigned me. Even though I've never used it, I still wonder about it and her. Group sex and gang r**e is HER kink and NOT mine. I wonder what her husband has knows or has figured out so far. She and her family have sugar coated everything that I know has been talked about.
At first I didn't want to be there. I liked to think of her as virginal. She looks and acts sweet and innocent normally, much like Sandra Dee. We watched tv, talked and waisted time until we were told by the boy coming out, whose turn was next. I was the last there so I was to be last. The first boy who finished didn't stick around much. He did stick around long enough to boast and tease that we were having his sloppy seconds. The other boys reminded him that he wasn't first tonight either. I wondered how many before him.
I was really conflicted. This was shattering my image of her. I was a virgin and had thought she was too. I learned this wasn't the first time here for half of them in the room. The only other boy that was invited for the first time was two years younger than me. I doubted if his equipment even worked yet. After two boys left it was just her brother and me as we waited for the other new guy to take his turn.
I was really mixed about this and admitted it to him. I asked him how long this as been going on. It started with their older sisters doing stuff like this. Now that she got involved Sandra Dee is taking it to a new level. I asked him if he ever took a turn. He blushed and looked down but admitted, he does. I coaxed out more. Part of the deal is if he plays a good host, he gets to go last, after all of the other boys had gone home. This sister is the only woman he's ever been with. I had to give him a break on that as he was only 12. Aside from that, she'll sometimes use him when an unrelated boy isn't handy enough. He was clearly conflicted about it too. He knew it was wrong but he was whipped.
The boy taking his first turn was his classmate. It is part of his role to find boys for her. She finds them on her own mostly, but she especially loves virgin boys and grown men. He helps finding virgins. He asked if I was upset that he invited me. He wasn't the one who called me, so at first I was confused. I then got that it was him that suggested me and gave her my phone number.
I asked what kind of boys got invited back. He didn't completely know all but he knew she liked the sweet ones that loved to eat her out but also the brutish ones that were jerks, strong, rough and basically r**ed her. She is obedient to them but bossy to the nice ones.
Although we were the same age, I was shorter and smaller than her most of our lives. Only now I was her equal. I was no equal to the two larger boys that already left. I was no bully anyways. I was going to have to be sweet. Eat her out. I didn't know what that really entailed but I was willing. All of these other guys wanted to use her. Even at 14, I wanted to marry her.
When the younger boy came out he was ecstatic and boastful. Having chatted with the brother, I felt like this might be his last time invited over. She called in her brother for a moment. He came out and told me she needed a few minutes to be ready for me. I wasn't surprised. She had done that, at lest somewhat, for each of the last two boys.
I wasn't sure what to expect, but my heart was in my throat and I felt shivers all over. I was nervous. Hi I greeted her. This was my first time having a one on one conversation with her. My brother tell me your a virgin. Oh crap, I think. I wonder what all he told her about me. Come on, she says as she led me to her bed.
She was dressed in a purple silky nightgown and nothing else. I didn't know why she put that on. We were going to be naked soon. She was just as soft, gentle and sweet and both speech and deed as I've seen her before. My mind was still being blown. She wasn't acting slutty at all.
I was a jumble of mixed emotions and clueless. She was a perfect first kiss. When she kissed me my eyes rolled back and I blacked out a second or so. I was in heaven. Each time she kissed me my lights went out. I still don't know what she does, but to this day, no other woman can make me black out just by kissing me. She ALWAYS could.
I looked and smelled all over her body and could not sense a trace of use on her. I was certain she had showered between boys, or at least before me. I was putty in her hands. When she guided me to her pussy I obeyed. She had to talk me through it. I was really clueless. I didn't know what she was supposed to taste like. I could be licking semen. I didn't care. I loved every moment.
I couldn't seem to get enough nectar out of her. I really didn't understand the biological aspects of all of this but I felt I could eat her out of her forever. Right then I was addicted to eating pussy. Not then, but several other times, I've found I can orgasm just from eating good pussy. After a time she got excited and stopped me.
She pushed me onto my back and started to lick and suck on my penis. My brain was on sensory overload. Each touch was super powerful to me. Only now I learned why ALL men love BJ's. She didn't finish me but suddenly moved up and mounted me.
I was again in Heaven. She rocked on me until she said her legs were cramping. She got me to get on top. It took a while to figure out what I was doing. I was in Heaven again. I wanted this NEVER to stop. I wanted to someday die while doing this. I was hooked.
I kissed and messed with her little tits. She asked about how she like them. I told her I didn't know. They were perfect. They were my first real tits. What I didn't say was that they were incredibly small. My sister is 2 years younger than us but her breasts are several times bigger.
When I came I said to myself that I was finally not a virgin and I lost it with the most beautiful and awesome woman on the planet. I didn't care if she was ever faithful to me. I was going to be faithful to her if she'd have me and marry me. I just had to stick around long enough to outlast the other suiters and win her heart. When I pulled out I was surprised to see a condom on. I had no idea how it got there. I didn't own one.
When I left her room the world was changed. I bumped into walls and walked with less control. During my walk home a group of men saw me and one told the others that he bet I just lost my virginity. I turned to them and asked how he knew. He said, Because you LOOK like it. He must be right. I wondered what I looked like as I walked the rest of the way home.
When I later met her brother, I told him that I'd like to be invited back as often as possible. I'd play any part, that I loved her and wanted to marry her someday. He replied, except for the last two parts I sounded like most other boys after their first time with her. Even though that didn't make too much sense to me but I took it as a compliment. Just tell me what I need to do or say to win her heart. He smiled and said he'd see.
As I got invited to more parties with her I got to know her more. I discovered, as sweet as she is, she is REALLY bossy. Even when we played gangr**e on her, she was clearly in charge. She set time, date and time, picked the boys, set the limits, gave the code words and decided when it was over. Fake gang r**e on herself was her favorite fantasy play. Pulling trains seemed to be her most common sexual activity. At least that was what I was invited to the most. Over time, I risked being more wild than the other boys to stand out to her more. It worked, I caught her approval. She gave me my own code word. In the far future, if I r**ed her without her knowing it was me, I was to say my code word just before I leave, so she's know not to call the police.
Most mixed gender times were actually naughty parties of a more party sort. Light drinking, strip poker, Truth or dare, 7 minutes in heaven, guess the tit/boner/pussy and such. She loved to invite boy-girl sibling pairs. Whenever a sibling pair was present she made certain to get them to mess around. The first time was ALWAYS without their knowledge. This usually took place as a glory hole of sorts. The guy or girl has to guess who is on the other side, servicing him, or being serviced by her.
When I found out my younger sister got invited to the same party as me, at this girl's house I knew what was up. I had plenty of time to talk my sister out of it, to warn her, prepare her or simply refuse to go myself. I didn't try any of that. By the time we were both invited I was eager. Brother-sister pairs are more often guests of her parties and I knew why.
My sister proved to be a good sport about being pranked into blowing me. On our walk home I told her the truth about how common it was. I told her about the brother and that was the known part of why. She asked me why I went though with it if I knew what was going to happen. I told her the full truth and pleaded with her to be cool with it all. I really wanted more time with Sandra Dee. My sister's help was key.
I got invited VERY often, with my sister, for a few years. My sister wasn't immune to Sandra Dee's charms and was gay for her really quickly. She claimed she wasn't into women, but my sister was hot for the same girl I was hot for. For one summer, Sandra Dee, was the girlfriend to both my sister and I. I was filled with jealousy whenever my sister had her to herself. My sister felt the same way when I had her alone.
My first FMF and only adolescent threesomes were with her and my sister. Anything I did with Sandra Dee, Sandra Dee made certain I did the same with my sister too. Sandra Dee loved those session and soon so did we. Sandra Dee never knew it, but we began to mess around when home alone. I never had a normal FMF again until I was 22. Not as often we swapped with her and her brother. While I liked that more, it was threesomes more than foursomes with her. During this time Sandra Dee was my girlfriend and my sister was his first girlfriend, officially.
As our relationship with her petered, on her part, my sister and I got closer. For just short of a year, my sister and I were essentially boyfriend and girlfriend as we both rebounded from being dumped by Sandra Dee. It wasn't ideal, obviously, but it was what we both needed. During this time we both got WAY better at our oral sex skills. I think my sister showed the most improvement.
Sandra Dee, never liked me the way I loved her. I still am Facebook friends with her. We've addended each other's sibling's weddings. She is married to a great guy who was clueless about her past when they got married. I don't know the details, but they adopted all of their children. She is still really bossy and so I'm thankful that I never got my wish to marry her. Still beautiful, I still think of her fondly. She has a great life and family.
As for my sister, we tapered off as we started dating others. Even though my sister is younger, she was more desirable so she got way more dates than me. At the end I was the one trying to keep our unique relationship going. She instead started fixing me up with her friends. That was decades ago. We still share sly grins at family gatherings.
I still know that code word Sandra Dee assigned me. Even though I've never used it, I still wonder about it and her. Group sex and gang r**e is HER kink and NOT mine. I wonder what her husband has knows or has figured out so far. She and her family have sugar coated everything that I know has been talked about.
