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My Start in Kink...part 2  

houndstooth 51M
35 posts
7/23/2017 5:30 pm
My Start in Kink...part 2


This is the second part, if you want to dtart at the beginning it is down below. This is a documentary essay about how I got started in kink. I owe it all to one special friend that I met early on.

One time when I came home for the weekend,she had been to the bookstore and had bought some toys. We spent that weekend trying them all out. She had bought herself a pink vibrating dildo and I became obsessed with using it on her. I loved driving her from one orgasm to another.

My mom and Lou were always very happy that we got along so well. We would go on vacations together, Kara and I wood be in the back seat together. Sometimes she would have her hand in my pants stroking my cock, sometimes I would have my hand up her skirt playing with her pussy.. we would take any opportunity to play. My mom and Lou would always get two rooms... One for them so they could be alone and one for Kara and me. They had no idea that once we were alone together our clothes were off and we were getting busy. It was on one of those family vacations that she first tried prostate milking. The whole way there she had been teasing me about playing with my butthole. When we finally got in the room and we're alone she had me get up on the bed hands and knees. I can distinctly remember the feeling of her two fingers sliding in and all the anticipation and nervousness. She warmed me up a little bit, and then zeroed in on my button. My hard cock would jump as she brushed across my prostate with her fingers. When she was ready to start she pulled my cock out behind me, and gave my spot nice little press. I felt the Heat and pressure of my juice being forced out, and she squealed with delight as my pre-cum began to flow out in a long ribbon. That was instantly one of her favorite thingsto do...mine, too.

We played a lot together over the next couple of years while we were in college. It was not unusual for us to fuck 10 to 15 times over a weekend. My college buddies would wonder if they were going to get laid on their dates...I never had to worry about sex. She would have boyfriends, I would have girlfriends, but we always made time for each other. She gave me a lot of first experiences; my first pegging, my first anal orgasm, my first cum kiss, urethral sounding...so many things. We had become very good at talking dirty, and really enjoyed saying very dirty things to each other...making promises and then delivering even more. She even arranged one of my first bisexual experiences with one of her boyfriends. That was very memorable . I had come home for the weekend to find her with a new boyfriend . I was wondering what I was going to do for the weekend when she called me into her bedroom she and her guy had just come out of the shower. When I got in there he was standing by the bed with his cock all hard. The head of his cock was remarkable...a big mushroom, with a well defined corona and a dark purple color. Looking back I am sure that she had picked him as much for herself as she did for me . She asked me if I wanted to suck his cock and as I was trying to answer she began pulling down my shorts. My cock was getting hard as well so it was impossible to hide that I was turned on. She led him over to the bed and set him down and had me kneel between his legs. She knelt down next to me and coached me through it. I think she was as turned on by watching us as I was doing the deed. She kept telling me how hot it was and was playing with her pussy . I kept going until he came in my mouth and she had me swallow . We all went to the hot tub for while and Kara asked if I wanted to see what it felt like to have a real cock in my ass. There was no denying it so we went back to the bedroom and he bent me over the bed. Kara was there as well spreading my cheeks apart and encouraging me. I'll never forget how wonderful it felt as the head of his cock made the breach, such anticipation and Kara squealed with approval as it did. It feltlt so awesome as his long shaft slowly sank deeper, it felt so warm. What's he got a nice rhythm, using a nice rolling motion from his hips. go I was in ecstasy, and it didn't take long and I was building towards an orgasm. Kara was watching closely and I remember her telling her guy
quot;I think you're making him cum! a little harder! That is so hot! a little harder!"...and then it happened... I blew a huge load with his cock buried in my ass. And that must have set him off, I felt the hot surge iof his cum coursing deep into my ass.

I also got to play a lot with her girlfriends. Most all of them had never seen and uncut cock, so she would use that. It would be hard for me to say how many times she called me into her bedroom and told me that so and so wanted to see my cock at the same time she would be taking down my pants, usually slow enough that my cock was already hard when it was showtime. She would have me stand there, and she would tug and caress my balls until my cock was raging hard. Then she would slowly start the reveal. They all loved to see her skinning back my cock and displaying my bare glans. She would usually start jacking me off, but sometimes she would ask her friend if they wanted to. Other times, she and her friend would sneak into the room when i was showering. Our rooms were connected by a "jack and Jill " arrangement. It was always a delightful surprise when I would see two or three forms appear through the glass door on the shower. I would stand there with my cock getting hard watching them get undressed...and then her sweet voice "Can we come in?" My cock would get so hard as they soaped me up and knobbed the hell out of its head. Not to mention how sexy they looked all wet with their nipples hard and hair hanging down. She gave me the nickname "Sir Cumsalot" because I could usually cum two or three times in a row while they worked over my cock in the shower. I would still be so horny when we got out. That always got things rolling in a most outstanding way. It would be a fuckfest the moment we had a chance. It was great for me because all of her friends were ballet dancers or people studying theater... They were always gorgeous. Kara had a way of tempting them to do extremely naughty things. For most of them, they had never had a guy with such practiced techniques go down on them, I really enjoyed showing them new levels of pleasure. That often would include their first experiences with anal...rimming and penetration. Kara would sometimes leave Sir Cumsalot notes on my dresser, giving me tips on what her friends wanted to try, and I was always happy to oblige. She loved showing me off. We loved giving her friends new experiences, especially the ones that found new orgasmic heights.. I can still remember the surprised look on some of their faces as they came harder and more than they ever had.

One of my favorite things to do to her was something we called ridingetrain. I would go down on her until she was about ready to come and then I would push in my cock and fuck her a little bit to make her cum all over my cock...an then repeat and repeat and repeat. When our folks were home I would have to lean down and kiss her when she came otherwise she would be screaming. She would kiss me so hard when she came ... It was awesome . I loved building anticipation with her and would call from college and tell her that I was going to make her ride the train when i got home...so by the time it actually happened she was so wet and ready my job was pretty easy. I could keep her going for about as long as I would want, and regularlyw went over an hour. Sometimes she would have me do it to her friends (she would join in) but usually I saved the best stuff for her .

She eventually discovered a way to make me ride the train as well . she would get me started by working a toy into my butthole, jacking me off right to the edge, peeling my foreskin way back, and then rolling it around pressing hard against my prostate. I would feel the warm rush of orgasm, and some cum would drain, but never enough to finish me. She would hold still until I calmed down, then work me right back to the edge . My cock would be so extremely hard, it would feel like it was going to burst! She was always able to tell just how far to push me without going too far.

Even when she got married, we would find ways to hook up. No one ever suspected a thing. Her first husband never had any idea how kinky she was. She got married to a new guy about 10 years ago and he is a kinkster as well. We have all played together many times but they moved to Portland about 5 years ago. Kara was the one who introduced me to Jinx a few months before she moved. We all had a while to play together, so Jinx was able to learn a lot about my favorites in a short period of time. And wouldn't you know...Jinx likes riding the train as well! We only see Kara a couple of times a year, but it is still a lot of fun.

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