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Blogs > rikkisucks > Rikki's sex life

My First Boyfriend  

rikkisucks 57T  
39 posts
4/12/2014 2:35 pm

Last Read:
3/24/2017 10:08 pm
My First Boyfriend

I have been dressing in women's lingerie and experimenting with dildos since I was a . The next step was to find a man to fuck me, but for many reasons, that didn't happen until I was 30. (I already posted the story of how it happened). This is the story of the first man to become my boyfriend.
I met Dave a few months after that first sex date. He was 53 and I was about 33. We met the same way I found the first man, through a telephone dating service. I answered his ad, and he responded. We talked on the phone a couple of times, and he sounded sane and made me feel comfortable right from the beginning. I told him that I liked to dress in lingerie, heels, and makeup, that I was still new at this even though I had just recently lost my anal virginity to a man. I also told him that I felt submissive with men, and he said that was fine, because he was a dominant type. He had to explain to me what a 'Top' and a 'bottom' were, and then we both laughed when I said I thought I was a bottom gurl.
We only lived about a half hour apart, so he invited me to come to his house in the country for our first meeting. The plan was for me to come as 'regular' me (not dressed as a gurl yet), and we would just talk, nothing else, and see if there was any attraction between us. I had no idea what was to come.
When I got to his house, we sat at his kitchen table and talked for awhile, and the mutual attraction was obvious. I wasn't really flirting because I was nervous and still pretty new at this, but he seemed very comfortable and made me feel the same way. Soon he smiled at me and said, "I think you're cute, Rikki." I smiled back shyly and thanked him, and told him I thought he was good-looking, too. Without another word, he got up and walked around the table, took me by the hand and helped me up, pulled me against him and kissed me. I didn't resist at all, I just fell against him and put my arms around his neck. That's all it took.
When he broke the kiss, he gently took my hand and led me to his bedroom. I was a little bit nervous that things were happening so fast, but not nearly as nervous as I had been on my first date. The only thing I was really worried about was that I wasn't in lingerie and high heels for him, and I said so.
"I wanted to be dressed sexy and make the first time special," I said softly. He told me there was plenty of time for that on later dates. Right now, though, he wanted to see just how submissive I would act for a complete stranger when it wasn't planned.
He had already told me his cock was 8" and uncut, and I admit I was excited to see it! I guess I already felt safe with him, and maybe pretty brave, too because I didn't try to stop him from doing anything he did next. I do know I was horny and getting more so by the minute. He started undressing me slowly, staring with my shirt, then my jeans and underwear. He was still completely dressed (I think now that's why I feel so feminine to be dressed sexy in front of a man that still has all his clothes on). Then he guided me back to sit on his bed. He got a set of leather ankle and wrist<b> restraints </font></b>off of his dresser, and put them on me. I just sat there obediently and watched him doing this, knowing I was about to be in a very helpless position with a man I just met, but it was getting me excited!
Once those were on, he helped me to my feet again, turned me around, and linked my hands behind my back. He told me to put my feet together, and then he did the same with my ankles. Next, I saw a leather collar go over my head, and he fastened this around my neck. He only spoke to me when necessary, and that made me excited, too.
He reached around and hooked a finger in the D ring on the collar, and turned me to face him.
"Ok?" he asked. "Yes," I said nervously.
He smiled again, and then led me slowly to his bathroom. I could only shuffle my feet to keep up. He reached into the tub and started the water. I saw a small hose from an enema bag hooked to the faucet, and I began to feel like he had planned this all along. But by that point I didn't care. I knew I wanted him. When the water was warm enough, he turned me away from him and told me to lean over the tub. I did, and then he pushed the hose into my ass. I can't even begin to explain how erotic it felt. When he thought I was full enough, he removed the hose and slid a small butt plug into me.
Now remember, all this had happened less than an hour after I arrived at his house.
Next he moved me around until I was sitting on the toilet, and then he took out his cock. He wasn't hard yet when he pushed it against my lips, but that didn't last long. I wasn't even thinking anymore, I was just reacting. He was so gentle and confident about what he was doing that he just made me feel like it was all natural and normal. He put his hands on my head and let me suck him for several minutes. Then he pulled back and turned around and put his asshole in my face. "Lick it, Rikki," he said. I had never done that before and wasn't sure I wanted to, but he pushed backwards while reaching around to pull my face against him, so I did it. It was kind of like the first time I swallowed cum....as soon as I stared doing it, I knew I liked that, too.
He let me rim him for awhile, and then he turned back around and put his cock into my mouth again. He was even harder now. He put one hand on the back of my head and the other on my stomach, and then he pushed his cock against the back of my throat while pressing on my tummy at the same time. He knew exactly what was going to happen. I gagged, which forced the buttplug and most of the warm water out of me. Then he pulled back and let me get a breath, and I saw him grinning at me. "That's a good slut," he said, and then he did it all again. He repeated the act about 3 or 4 more times until I was empty. When he stepped back, I looked up at him, trying to get my breath back. I was a little bit scared now, but he kept talking in that soothing tone and told me he thought I was a very good slut. I had never been called that before, either....and I liked it.
He helped me up and led me back to his bedroom. He told me to bend over and lay face down on the bed, but keep my legs straight and spread wide, and he pushed them even farther apart with his foot. I could see back between my legs as he put on a condom, and then he asked me for the first time if I was enjoying this. OMG YESS! I said, and I meant it.
He fucked me in the ass until he came in the condom, and later he released my wrists and I sucked him until he came in my mouth. When he was done, I got dressed, we kissed at the front door, and he invited me back the next weekend. Of course I said yes! He told me to come dressed as slutty as I wanted, but I could put regular clothes on over the top if I wanted to. From now on, he said, whenever I came to him, I should dress and act like a gurl.
For our second date, I picked out the nicest lingerie I had. I did wear jeans and a top over it, but I decided that since I was already wearing my wig and makeup, I might as well wear my high heels instead of carrying them. I was already pretty good at walking in them, but I had never driven in them. He seemed to like what he saw when I got to his house that evening. He took me directly to his bedroom, and we made love and kissed and fondled each other for the next several hours. I got home very late that night.
Our third date happened about a month later. It was alot like the second, but I was getting more comfortable with him and acting my role as a gurl. At some point in the evening, in missionary, he looked down at me and asked me if I wanted to have a boyfriend. I had never really thought about it, but I really liked the way he treated me. He suggested we both get tested for std's, and that we would only see each other so he could fuck me bareback. I knew that was going to be a huge step for me, but I really wanted to try it, so I said yes.
He made the appointment for a couple weeks later and even drove us there. After that, he always fucked me bareback. The first time he got on top of me and slid his naked cock into my pussy was when I knew I was his gurlfriend. And when he came inside me, it felt incredible! The intimacy we shared of having his cock inside me when he got off was such a beautiful experience. The hottest part about it for me, was knowing that I would be carrying his seed in my body for the rest of my life. That's still a huge turn-on, even now.
I didn’t date anyone else except him for 2 years. The sex got more creative each time, and most of what I know now I learned from him, like taking his cumshots all over my face, tasting and eventually swallowing his piss, fisting, rimming, and BDSM. We even slow-danced in his living room, him fully dressed and me in high heels and lingerie. Dave was the man who introduced me to bondage and discipline. He was good at finding out what I could take or what I liked, and just as good at pushing my limits to get what he wanted. Most of the time I couldn’t refuse him. We played all over his house. He had a screened-in sun porch on the back of his house, so in the summer we usually played there or outside. He had a big backyard and neighbors that were close (but not too close), so the fear and thrill of being seen was always there (I don’t think we ever did). We didn’t do any really weird, uncomfortable bondage positions, just simple ones where he could spank me or crop my ass or fuck me without ever untying me.
One of the greatest moments in our relationship for me when he made me cum just from fucking me. I didn't have to touch myself at all. We were in missionary, him leaning over me and I had my arms around his neck. He was hitting me just right and it was so passionate, and it just happened. I didn't even know that was possible. When I felt it coming, I let out a long moan and Dave just kept fucking me and fucking me, all the way through it, and I started crying. He smiled at me and kissed me, and that just made me cry harder. Not long after I came, Dave came too. It was the most beautiful experience I have ever had in bed with a man. It was almost like the ice was broken, because after that he fucked me into orgasm more often. Not every time, but when he did it almost always left me in tears of joy.
It was in our second year when he brought in two friends of his to fuck me, but I didn't know about it until we were already in bed one night. We were making love with Dave on top, and I heard a knock on the front door. The next thing I heard was the door opening! I looked at Dave in shock, but he just smiled and kept going. "Tonight you get to live one of those fantasies you told me about," he said, and then they were there, standing next to the bed!
One was white and older. The other was younger and black, my first. To this day he is still the biggest cock I have ever had: 10 beautiful inches. Both of them wore condoms with me except when I sucked them. I was immediately very nervous, but I trusted Dave, so it turned out to be very exciting. That one lasted literally all night, and I could still feel what they did to me about three days later.
Dave eventually transferred to a new job out of state, and we lost contact. I know I owe a lot of my sexuality to him. It wasn't until years later that I realized what a lucky gurl I was back then. A few guys who have heard this story have asked me if I was in love with him. I wasn't sure at the time, but I still have very fond memories of our time together.

sonnny49 92M
Ask me for a photo

6/2/2016 11:26 am

 utterly fantastic


rm_LisaCarver 60T
487 posts
5/29/2014 6:02 am

 Thank you for this post, it was good.


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