Loading...‘Strap-on fucked’. . . the phrase alone sounds so depraved, but I found out that it doesn’t have to be. Well, hell, maybe it is, but perhaps that’s the fun of it! I came to this realization a few years after college, when I was dating Emma. She was short, with dirty blond hair, and a mischievous smile. She was not skinny, but not big either; she was sorta pear-shaped and curvy, which was strangely attractive when she would walk naked through her apartment.
We met in a bar one night. She was with a friend and I had been feeling lonely. We struck up a conversation, and we wound up closing down the place. We went back to my house that night, and actually, nothing happened other than a little making out. We fell asleep together and went for brunch the next day. However, that led to a bit more. . .
Emma and I had been dating for a couple of weeks, and the sleepovers became more frequent, as did the oral sex. She was the first and only woman that I had ever been with who swallowed. She was particularly talented at giving head, which she seemed to enjoy. Always, when she felt my body begin to quiver and my cock start to spasm in her mouth she would violently deep throat me and I would cum in the back of her throat. Her tongue would continue to work the sensitive underside of my cock, milking me dry.
As we were both fans of fair play, I would either return the favor, or she would be returning the favor to me. She received almost as well as she gave. Emma was always easy to get going — as soon as I touched her clit, you could feel her become more alive. She was shaven, so there was never anything in my way to prevent me diving in, tounge tip first. She tasted tangy and a little sweet. And you knew when she was about to explode — she instinctively dug her fingernails into my arms, my back when she was about to cum. It was a good kind of hurt, and luckily none of my coworkers at that time asked why I occasionally had little crescent-shaped scars on my arm.
In any case, it was the frequent oral that got me to the event which led me to write this story. One night, as she was performing a “tongue job,” she slipped her finger between my buttocks and gently flicked her nail across my hole. She could tell from my involuntary jerk that I was surprised, and she apologized, along with the mischievous smile that I mentioned earlier. She had incorrectly assumed that I didn’t like it, and I told her that there was no need to be sorry. She smiled again, tossed her hair to the side and resumed sucking my dick. This time, though, she was a little more aggressive with the finger. I loved it, and at the same time, I felt a little violated and naughty — I’m a man, am I supposed to like this? I didn’t care. I relaxed and she slid the tip of her finger into my anus, just massaging the opening. Naturally, it didn’t take long before I was, again, coating her throat with my cum.
We laid in bed talking that night. She asked if anyone had played with my ass like she did, and I answered honestly, that no one ever had. I was also honest about how much I liked it. She didn’t seem to be freaked out by this response. She told me about an ex-boyfriend of hers that got her into anal sex. She didn’t love it, but he did, and she didn’t really mind doing it for him now and then. She went on to say, though, that he really liked it when she played with his ass, too. They started out by getting him a small anal plug which he often wore during sex. That led the two of them to purchase, you guessed it, a strap-on for her to wear. After a while, though, they grew apart, but she still had the strap-on. Emma could see that I was intrigued by all of this, as my cock slowly came back to life while she was talking so casually about something that seemed so taboo. She started stroking me and asked if I wanted to give it a try. I said that I didn’t want to that night; it was late and I had already had a good orgasm. However, I did say that it may be fun to try in the future.
So, I thought about that night for a couple of days, and what can I say — it made me horny. I called her to ask her to dinner the next weekend. We went to an Italian place we both liked and talked about whatever people talk about on dates. The restaurant was closer to her place than mine, so I accepted the unspoken invitation to continue the evening at her place. We drank a bit of wine and watched the last part of an old movie on TV. I had enough wine to be a little under the influence, but certainly not drunk. We turned off the TV, and I looked at her.
” I think I want to give the strap-on a try if you don’t think it’s weird.”
She smiled with the side of her mouth, and said, “You know I don’t think it’s weird. I thought you might bring that up.”
I was a little embarrassed, but it didn’t matter, I was already starting to get stiff just thinking about it. She took my glass and held out her hands, silently coaxing me off the sofa. I took her hands and she led me to her room (as if I didn’t already know). She turned into me, and we kissed. I began to undress her — I slipped her out of her shirt and bra, kissing her neck as I did. I pulled the skirt she was wearing over her hips, and it hit the floor. She began working on my belt and pants as I pulled off my shirt. Free of our fabric restraints, except for a satin thong that she had on, we collapsed onto her bed. I licked my way down her torso, and she helped me slide out of her panties. I consumed Emma’s peach, I did my part.
After her ecstasy wore off a little, she lowered her mouth on my ready member and gently sucked. It didn’t last too long, and for once, I didn’t want it to. She got up, went to the closet, and reached up for her “toybox.” She pulled out a black latex dildo, which was fairly normal size (for which I was thankful) and a harness-looking thing. Emma fitted the cock into the strap and fastened it around her hips. Then, she pulled out lube which she stroked onto the fake penis that she’d soon slide into my ass.
“Are you ready for this?” she asked.
“Oh, yes,” I replied, ” I think so.”
“Well, hands and knees, then.”
I complied with the command. It felt really odd and vulnerable to stick up my ass in front of a girl as if I were a cat in heat — but it was exciting. I felt a lubed finger slide between my cheeks, and Emma pushed the tip of her finger into my hole. Again she just massaged, and I relaxed.
“This is to loosen you up a bit; I don’t want to hurt you.”
I didn’t respond, I just felt. A moment later she began to slide it in. I felt the cool, wet tip of the cock press against my opening. I pushed back a little and the tip slid in – I exhaled violently.
“Does it hurt,” she said.
“Not really, I just need to get used to it.”
I nodded, and she slid a little deeper. This was good, and I moaned. She began to work my ass in a slow rhythm now, and I was really enjoying it. I found that I liked the feeling of her in control, the feeling of being fucked. She grabbed my hips and buried the cock into me. We were still for a moment. I could feel her warm, smooth thighs pressed against the back of mine. I was being fucked, doggystyle, by a woman. We started to move again, this time faster. My ass felt full, my cock was erect, full, and heavy. The motion of being fucked from behind was causing my cock and balls to just dangle and jerk around with each thrust, which was odd but wonderful. Emma kept slamming her pelvis with her fake dick attached into my ass — the pressure against my prostate was about to make me cum. I reached back and stroked my cock maybe 5 times, which was all I needed to make me explode.
I came on her sheets, but didn’t care. I collapsed forward, and she with me. We both caught our breath, and I apologized for the mess. She slowly withdrew from my ass, laughed and said that she didn’t care — sheets can be washed. We cleaned up, changed the covers, and fell asleep naked, soft , and warm. It was kinda sweet for something that sounds as depraved as being “strap-on fucked.”