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By (user no longer on site) OP
over a year ago
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This chapter got missed initially. It fits between 3 and 4.
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This is the (more or less true) tale of the next step on my long journey to where I find myself today, please comment – feedback both good and bad is equally welcome.
Well, following our fun at The Cottage, Pat and I had a few more meetings, sometimes alone and sometimes out and about. The thing that had struck me at that first outing to The Cottage was how much I had enjoyed a finger inside me at the point of orgasm. I had kept quiet about it for a while not even really admitting it to myself. Eventually my horny imagination and desire to experiment got the better of me.
So I took a trip to a local sex shop, and bought myself a vibrator, smooth sided and not too big. I also picked up some lube and condoms. I was excited, and planning to rush home and try it out when another thought struck me. En route I stopped off at a Department store, Debenhams I think. I took myself to the lingerie department and bought myself a pair of black fishnet stockings and a black suspender belt with matching black knickers. I found the whole experience a bit embarrassing, but exciting at the same time.
I drove home with an excited flutter in my tummy and a raging hard-on. As soon as I had parked outside my place I rushed in, and stripped immediately. This was the point at which things changed for me for ever. With trembling hands I slipped the stockings on, revelling in the kinkiness of it all. Next the suspenders, which I spent an age struggling with until they were fixed and finally the smooth silky panties. I felt wonderful, and my cock was as hard as I had ever known. I walked to the full length mirror in the hall, and was so thrilled to look at myself dressed in undies for the first time in my life.
I grabbed the other purchase of the day, the vibrator, and ripped the packaging apart to get to it. I dropped the black panties and stuck a lubed finger into my bum. I recall how easily it went in, and I also recall how much I enjoyed stroking the finger in and out. I reached for the vibrator and with trepidation and excitement eased it into my virgin hole. It felt tight but not especially painful, and with a bit of pushing and wiggling I was delighted to find I could take the whole thing, but it felt rather dry when I tried to thrust it in and out. I was later to learn that more lube would have made the whole process easier. Looking back I need not have been surprised at my ability to accommodate the whole thing, as it was actually rather a small one! I found that the actual penetration, which was fine as far as it went, was nowhere near as pleasurable as playing the vibrating tip just inside my anus. I spent a happy afternoon lying on my bed, feet in the air, teasing my butt hole with the vibrator and wanking myself silly!
This became my new hobby for a few months and I added to my collection of undies, loving the feeling of them against my body. I even shaved my legs, and thus discovered the absolute sensual pleasure of smooth undies against smooth skin. I was lost in my own one man orgy of self indulgence.
By this time Pat had gone quiet for a bit, so I found myself trawling the free ads again looking for a meet. This time I wanted to meet wearing my undies which had become a passionate obsession of mine. I had a few fumbles with some similarly undie attired cross dressers, mainly mutual masturbation and getting sucked. I Remember I did suck one guy briefly, but again lost my nerve before he finished, so I finished wanking him over my stockings. These meetings were fun, but didn’t match the thrill of a fully dressed and dolled up transvestite.
It was then that another memorable lady came along. Suzie. The delightful Suzie. We arranged a meet at her place, which was a mobile home on a park on the edge of town. I arrived and was shown in by a slightly older, slim, petite TV. She was dressed in a satin blouse, black pencil skirt, and very high black patent stilettos. She had very long red nails, curly red hair and very precisely applied make up. I recall that she was also wearing a very heady perfume. I was mesmerised.
She showed me in and we sat together in her living room, chatting over a glass of wine. I told her of my experiences to date, and she told me tales of decades of debauchery. As we chatted, she stroked my thigh through my jeans, her hand inching higher until she was gently brushing my straining bulge. She leant forward and gently kissed my lips and at the same time expertly undid my jeans. Her hand slip inside and began caressing my pantie clad cock. I loved the feeling of her long painted nails tracing the outline of my erection through the silky material. My clothes came off and before long I was sat on her sofa in only stockings, suspenders and panties. Suzie called me a “delightful little sissy” and told me that the undies were the first step on a slippery slope.
Taking me by the hand she led me to her bedroom, gently pushing me back onto her bed. I felt helpless. Susie looked down at me and said “Hmmm what can we do with you?” She opened her wardrobe and produced a long black negligee whish she helped me into. The feeling of it slipping over my stockings and panties was sheer heaven and I felt my cock twitch. A pair of heels were also produced which she put on my feet (with a bit of a struggle – they were a size too small). I recall laying on her bed, helpless and trembling at the sheer eroticism of it all. Suzie sat on the bed alongside me and resumed he gentle stroking of my erection with her nails. This time it was through a double layer of satin, and felt better than anything I had experienced before. “You really are enjoying this aren’t you?” Susie said, and with a trembling voice I said “Yes”. She smiled at me and stood, then reached behind herself and I heard a zip undo. Following that Suzie’s skirt fell to the ground, and she stepped out of it. I could see her beautiful shaven cock and balls nestling within a pair of delightfully sheer french knickers.
I knew immediately what I wanted and reaching out I gently eased her hardening cock out of the knickers and began stroking. As she reached full stiffness I leant forward and took her in my mouth. “Oh that’s it darling, yes. Suck me. My little slut.” I was a little shocked to be talked to like this, but also excited. I stroked the underside of her smooth balls and slid my mouth up and down her shaft. I can still remember the smell of her perfume filling my nose as her hardness filled my mouth. I felt her hand on the back of my head and then Suzie began to thrust into my mouth. I sucked for all I was worth, carried away with the experience, loving the smell, the taste, the feeling.
Throughout, Suzie was talking gently to me, “ooh that’s lovely, you are my special little cocksucker, you naughty sissy”, all of which was causing me to put more and more effort into pleasing her. My hand drifted back from her balls in order for me to slip a finger into her bum, but as I did so I got a shock. My middle finger felt plastic, not the soft warmth I was expecting. I must have flinched or something, because I felt Suzie’s hand press more firmly on the back of my head pushing me back onto her cock. She laughed and said “Didn’t expect that did you? It’s my butt plug!” I put my hand back there and pressed against the exposed end of the plug, and noticed that each time I did so it seemed to make Suzie’s cock a little harder. It also made her gasp, which I took as a good sign and carried on doing it. I wasn’t prepared for the results however – without warning, I felt a warmness inside my mouth, and a groan came from Suzie as both her hands pressed on the back of my head. Before I had even realised what was happening I swallowed and tasted a bitter, salty taste whilst at the same time Suzie pushed forward, making me gag. All at once it was over and I looked up at her as her cock slid from my mouth. “Oh my God, was that what I think it was?” I asked. “Yes daring” was the reply, “You made me come!” The shock I felt was incredible, as was the buzz I felt as the realisation sank in. “You are a proper cock sucking slut now!” said Suzie kissing me gently on the forehead. “Now, time to return the favour”
Suzie knelt next to the bed and urged me to sit up. She leant forward and lifted the negligee, and pulling me out of the silky panties took me into her mouth, swirling her tongue around the tip, then plunging down to take my full length. She bobbed up and down, sometimes sliding along my shaft, sometimes nibbling the end, but all the time sending waves of pleasure through me. I gasped, and moaned almost unable to take the sheer ecstasy I was experiencing. The way Suzie used her lips, tongue teeth and throat was truly mind blowing, the best blow job I had experienced. All too soon I felt myself clench as my orgasm approached, and with a wave of release I cried out loud as I came in Suzie’s mouth. She carried on, sucking hungrily and moaning till it all became too much and I had to beg her to stop. She smiled and kissed me on the lips, pushing her tongue into my mouth. This time I recognised the taste, a taste I was to come to love. |
