My first strap on

My first strap on My first strap on

Status: Finished

Genre: Erotica

Details

Status: Finished

Genre: Erotica

Summary

My first experience with a strap on and with a woman taking control

Summary

My first experience with a strap on and with a woman taking control

Content

Submitted: September 17, 2013

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Content

Submitted: September 17, 2013

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I have been asked more than once, when the first time was a woman used a strap-on with me. The first time was when I was a junior in college. I did some amateur stripping to make some extra money in those days. I was not big and buff so I was not overwhelmed with jobs from the agency, but I had steady enough work to make it worth doing. One of my jobs was the typical “bachelorette” party for a group of about twenty women. The bride-to-be was a little older so the age range of the group was 30’s and over. It was a good show and women usually tip well.  On this occasion, one a woman approached me after I had finished stripping and was packing up to leave.

She was very flirty and obviously wanted to meet me later. While this did not happen as much as you might think, it was not the first time. The problem with such offers is that there usually is a presumption that you will have sex for money and despite everything, I was not a prostitute. I was polite but firm in that I could not meet afterwards. She was friendly about it and did not argue, but she wrote her name and number down and gave it to me, “in case I changed my mind.” The few times that had happened to me in the past I would say thank you, take the paper and throw it away later. But I took a good look at this woman. She was older than me, in her thirties (I was 20 at the time), but she was very fit and had an excellent body. Her face was pretty but it was her eyes that caught me. She had this way of looking at me that was sexy and very powerful. It was like she was enjoying me, just with her eyes. It literally sent shivers up my spine. I took the paper and put it in my pocket.

Over the next few days I found that I could not get my mind off this woman. I figured I would end up throwing the piece of paper away but I did not. I kept hanging onto it. After several days I finally gave in and decided to call her. “Julie” was written on it with a phone number. I dialed the number and actually was a little nervous, like I was back in high school! She answered and I asked if this was Julie. She said yes and I told her who I was. She seemed pleased that I called and asked if I would like to get a coffee. Within an hour we were both sitting at Starbuck’s sipping our cups.

Julie was totally engaging! She was a single business woman and clearly was self confidant but not in an arrogant way. She seemed genuinely interested in my studies and my background and we chatted quite a while. I was half expecting her to offer money to me and suggest a hotel room right on the spot. Looking at her body and enjoying her company so much I am not so sure I would have stuck with my principals and said no. Instead she finished the conversation by suggesting dinner that weekend. I readily agreed and gave her my number. I have to admit that it might have been the stereo-typical younger guy/MILF infatuation for me but it was intoxicating that such a confident, sexy, self-made woman would find ME attractive! I admit it turned me on.

To make a long story short, Julie and I started dating fairly regularly though we never made it exclusive. I still dated some girls at my college and I knew she was seeing other guys. But on the second date we had sex and it was awesome! Her confidence extended into the bedroom and I have to admit that she was often better than some of my more clumsy encounters with girls my own age. And it was clear to her that I was willing to let her take the lead in the bedroom too, which is exactly what she was looking for.

I think it was about a month into our dating and maybe our third sexual encounter when she suggested using a strap-on. I was very surprised. Even though she clearly enjoyed having control, she did not seem like the leather, whips and chains type. She explained that dominance was not necessarily the same thing as S&M. And obviously attempting to soothe my male ego, explained that being dominated was simply another sexual choice and did mean the guy was a “wimp” or a “sissy.” Whether most guys want to admit it or not, I certainly had played with my ass before while jerking off. But I was hesitant. Julie told me we could go slow at first and I could tell her to stop at any point. While I was hesitant I was also curious and I truly was turned on by this woman in so many ways. So I agreed and the happy look on her face alone almost made it worth it.

We were already naked and in bed but had not really started. She got up and walked to her closet. She brought out the harness and strap-on and showed it to me. I admit I was little intimidated but I decided to try it. She put it on, spread some lube on it and then kissed me. Then she told me to turn over and lay flat on my stomach and spread my legs. I did this and I could feel her hands spreading my butt cheeks to reveal my hole. She talked me through the whole experience, probably to keep me at ease. She told me she was putting a little lube around my hole and I felt her finger and the cool feeling of lubricant on the opening of my hole. Then I felt the tip of the rubber strap-on against my hole and she said, “ok I am going inside you now.” I tensed up and could feel the tip of the strap-on slowly push past the opening of my hole and slowly make its way down my anal canal. Julie told me to relax and I could feel her hands massaging my butt cheeks. After a bit of coaxing and sweet talk from her, I finally did relax and I could feel her moving the strap-on slowly inside me. She took short slow strokes at first and asked me how it felt. I told her that it was a bit uncomfortable but it did not hurt. She said it would get better.

She started to take longer strokes and started to massage my lower back. I could feel the strap-on rubbing against my anal walls and as the lube worked its way around, it moved more freely. I concentrated on relaxing my anal walls and she picked up some speed. I felt her weight on top of me and her hips grinding as she moved the strap-on in and out. It still felt weird to me but I was getting more comfortable as she fucked me.

She stopped and asked if we could change positions. I said sure and felt the strap-on withdraw. I turned around and lay on my back. She told me to put my legs up in the air and when I did, she grabbed the back of my ankles and pushed my legs back. This raised my ass a bit and exposed my hole more. She moved her hips to put the strap-on tip against my hole. She asked if I was ready and I said sure. She pushed it in and I gasped this time. It felt different than when I was on my back and it was rubbing against my prostrate more. Since I was already “loosened” a bit, the strap-on slipped inside me more easily and she started with longer and faster strokes. Despite whatever misgivings I might have had in the beginning, this felt good. And then I looked at Julie’s and saw this look of hunger and pleasure on her face, that really turned me on. She was really getting off on this! I guess I was surprised that a woman would actually enjoy this, but clearly Julie was into it. I asked her something like, “you really get off doing this, don’t you?” And I will never forget her answer: “I love it when a guy lets me use him.” Some guys might be turned off by the thought of “being used,” but when she said that, something awoken in me. All of a sudden, I wanted to please her, wanted to see and hear her get off. I truly wanted to be used by her for her pleasure. And being the instrument of her pleasure was a huge turn on for me!

I looked into her eyes and said, “oh baby, use me good…..” Her eyes flashed and her smile broadened. She knew she had won me over! She started to fuck my hole with more vigor and I could feel her hip bones against my butt cheeks. She kept it up for several minutes and worked my ass good. She then withdrew and told me to get on my hands and knees. I quickly obeyed and found I did not mind obeying. She then began to fuck me in the classic doggy position and now she was not holding anything back! She was pounding my ass and I was gasping and moaning. At one point she grabbed the hair on the back of my head and pulled and I just pushed against her more. Then she reached in between my legs and began to jerk my cock as she fucked my hole. I came almost instantly and shot a huge stream of cum onto the bed beneath us. She slowed her strokes and then gently withdrew the strap-on from my rear. I literally collapsed onto the bed and all I could say was “wow.” Julie crawled forward and lay next to me on her back, the strap-on now pointing towards the ceiling. She chuckled slightly and rubbed my back. I looked up at her smiling and said, “does this make me your bitch now?” She laughed and responded, “only if you want, babe!” I moved forward putting my arm across her stomach and buried my head on her shoulder, saying, “I have to say….I’m okay with that…..”


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