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Losing My Virginity

Taken for the first time
If you are under 18 years of age or are not interested in these explicit topics please do not read this story. This story is true- even toned down some what. My first story, hope you enjoy it. I apologize if it is too long. As I said, it is my first writing endeavor of this type. I hope to put some more up-many will be fact some will be fiction.

Several years ago I joined a site to finally find an attractive female who was dominant. Someone to help me explore these fantasies, deep desires. I found someone, who was interested in spanking, being Dom and anal play. We chatted for a while via the site for some time. We had other mutual interests-wine, film, the arts, dining out, traveling. After about 2 months of chatting, she disappeared off the site.

After about two more additional months of time passing, lo and behold I saw her back on the site. I immediately contacted her. She explained she left the site having met and old flame,which to my advantage,didn't work out. She said she returned to the site just for fun, not looking to "hook up" I was persistent. Then one day after a terrible lightening storm, I head this garbled message on my answering machine. Completely inaudible but it was her!. After going on that site and opening up my mailbox, she left me a message, saying she tried calling me and heard a garbled greeting on my answering machine, not sure if she called the right person. She left me her personal e-mail so I could contact her. With some trepidation, I emailed and asked for her number. I could feel the butterflies in my stomach-like calling up a girl for your first date- as I picked up the phone to call her.

Our conversation was pleasant. She was ready to give up on me after hearing that garbled intro on my machine, my voice intro having been destroyed by the lightening storm. We exchanged pleasantries and we agreed to meet for dinner. I off course trying to impress her, brought some of my best wines-'97 Barolla and Amarone, a Moulin -a-Vent, and a great Chardonnay. After a pleasant dinner and conversation we chatted about our sexual interest- she enjoyed spanking, being Dom, strap-on play and more. She was quite knowledgeable. I was clearly the neophyte-she now knew she had control over me. I expressed my desire and fantasies of being dominated by an attractive, sexy woman such as her. I also expressed my need for privacy and discreetness. She fully understood, as she had a vanilla life of her own, which included acting and writing, but also enjoyed writing stories on spanking and strap-on play on other erotic sites.

At the end of the evening, I walked her to her car. It was a warm May evening, she looked good in her white dress with red stripes and heels. The breeze lifted her dress up a bit. She looked great. We kissed. We sat in her car. Then I, with great uncertainty, asked her the Million Dollar question-"May I see you again"-yes. Great!

We met the next week. We went to a movie-nothing happened, but she showed me an array of some (but not all) of her toys. I stared in awe and was getting excited. There was a small butt plug, cuffs, a paddle, belts for strap-ons and some vibrators. She wouldn't use them on me tonight because she wasn't sure about me, nor thought I was ready. I was as so excited, I wanted to FUCK HER RIGHT THERE! No way would she let me. I was hard as a fucking rock! I told her I was hard and needed to cum. She said I could jerk of at her feet if I wanted, but that was it. She wouldn't touch me. I slowly undid my pants, I took all my clothes off. I always thought it ridiculous in porn movies where guys still had there socks on after getting naked. I was determined not to look ridiculous. She told me to get down on my knees. I did and I slowly began to stroke my cock. It was like a piece of hot steel. She rubbed my dick with her foot. She was so sexy, and it was so erotic listening to her describe what she would do to me when the time came. After about 10 minutes of stroking, I shot my load over her legs. She gave me a devilish smile an asked me to get some Kleenex. I asked her out again and she readily agreed.

Our next date was in the city at her friend's party. I felt out of place at first-all these people who were involved in the arts. I warmed up and we all had a nice time. As we were walking to the car a heavy down pour started. We were on either 6th or 7th Ave-downtown. As luck would have it, she said we should duck into the store that happened to be open across the street until it stopped raining. At 1:00 am in NYC, the only stores/places open are drug stores, pizzerias and sex novelty shops. Guess what place she choose! Well now I am like a kid in an candy store. She acts like she is taking her usual walk through the park, sashaying her way down the aisles, asking about this or that item. Totally second nature to her. Myself, I am excited, and yet somewhat meekish here. She has this lovely grin. Her big brown eyes staring at me "this is what you want , isn't it." Teasingly, she points to items saying I am not ready for those-yet.

On our fourth date I take her to a movie. We stop for some drinks afterward. I am starting to think that nothing is going to happen with her and may have wasted my time. Perhaps she was all talk and no action. After the drinks I took her to her house. When we got to her house, we hung out on the couch, we started to kiss. My hands made my way up her dress. She wasn't wearing any panties (she said she seldom wore them), she was getting so hot. My cock was leaking cum and soaking through my pants. She decided to take me upstairs. She took her dress off. She had this sexy black bra on and her heels. She unbuckled my pants and began to stoke my cock, I was leaking and also shaking with anticipation. Was this going to be it? We were kissing, then she pushed me on the bed. I was like putty in her hand. She rolled me over on my stomach and massaged me then slid her finger down the crack of my ass. Without realizing how quickly it happened, my hands were tied behind my back. She left the room for what appeared to be at least a half hour. Next thing I heard were footsteps coming up the stairs. I was so nervous, and there was some fear about this. I thought to myself "Be careful what you ask for you might get it"-well now I was going to get it. It was surrealistic. I so nervous in anticipation. Here I am lying face down, on her bed, totally naked and vulnerable, my ass totally exposed for her pleasure.

Next thing I feel is stinging pain. She has taken out a paddle and began blistering my ass with it. I beg her to stop. But she giggles and says she is being easy on me and that I am just baby/beginner. She said you wanted this now you got it. My head is spinning at this point. I am asking myself "what the fuck did I get myself into." After about what seemed like an eternity (but probably only about 5 minutes of spanking and her verbal teasing of me) she stopped. Next she rolled me over and stood back. My eyes popped out of my head. She stood before me, looking as hot and sexy and Dom as I could imagine. There she was staring at me with her hands on her hips, red lipstick, piecing brown eyes and a wicked grin. She was dressed in black stockings (I think they may have been fishnets), black high heeled boots over the knees, black corset, and this thick 6" inch pink strap-on dildo. Nothing sexier than a hot chick in heels and lingerie. I had so many emotions going through me, excitement, fear, embarrassment, humiliation. I was about to experience one of my most erotic fantasies.

She slowly walked toward me then straddled me on the bed, her legs between mine, forcing me to be spread wide. She began to kiss me, slipping her soft tongue into my mouth. Then she fed me those firm beautiful breasts. She moaned as I sucked on them and bit them. Her hand slid down to my raging hard on. I am thinking that this is really going to happen. No turning back now. I am so excited. She tells me my ass is hers now. She flips me back over and teases my ass with her finger, saying she is going to take me like a virgin. I feel a cool and slippery lubricant put into my ass. Next I feel her finger. I clench my cheeks, which is met by a sharp stinging slap on my ass. She says to relax-it will be easier. I've come this far and she says its time to go all the way. I feel my ass being massaged by one then two fingers. The discomfort becomes easier to take. She found my g-spot. I am starting to feel great pleasure. My dick is leaking pre-cum.

As I my mind starts to drift away, she abruptly pulls her fingers out and flips me over. She stares right into my eyes and says "now I am going to fuck you." She slowly starts to impale me. It hurts, she tells me to relax and try to open up, but it still hurts. I want to say stop but I can't. My hard dick gives me away. She starts to pump me and now I start to feel the pain and pleasure. The thoughts of humiliation fly trough me, yet I can't deny how good this feels. She tells me to open my eyes and look at her. She says she loves to look into the eyes of the person she is fucking and watch how she stretches his ass and knows there is nothing he can do about it. That she is in control. The strap-on further excites her as it rubs her clit. The power trip and role reversal is a tremendous turn on for her and me. The humiliation and feeling of my being helpless increases my excitement 10 fold. She picks up the pace and is really pounding me, telling me she now owns my ass and will fuck me whenever she wants. I am hard, everything seems dream like. She now starts stroking me while fucking my ass. She keeps asking me how it feels. I am embarrassed to say it feels great but she wants to hear me say or she will stop. I give in. Now she pumps me harder and strokes me faster. I beg her to make me cum . She says not yet! After about about 20 minutes of this ass-fucking she finally says I can cum now. She fucks me hard and strokes my cock more and more, faster and faster. Suddenly my balls tighten and I arch my back and shoot a huge load with such intensity, that it actually hurt in my groin. I cum for about 1 minute shaking. It was incredible. The best orgasm I ever had! My legs felt like a rubber snake at this point. I couldn't even stand up when she untied me.

Once untied, I licked her pussy then fucked her the rest of the night-even in her ass. We chatted about the whole experience. We both stated how erotic and hot the experience was. We both enjoyed it immensely. There would be much more playing like this in the future. What an evening!

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