As I turned to cover my semi-erection, I told her I would like a matching set of bra and panties in a 38b bra and size 7 panty, or a chemise, camisole and matching slip or a teddy or a nightgown that my sister might like in a large. She leads me over to a table full of all different color and sizes of bras and next to it the table with the coordinating panties. As Cindy showed me different styles of panties and bras in the different colors and materials, and was talking about how pretty they look and what might look good on and what is more comfortable than others, I became fully erect. Cindy then stepped in front of my and brushed the stiffness in my pants and said, "Mmm what do we have here?" She put her hand on my crotch and began to rub my erection. As she rubbed, she caught me checking out what she was wearing under her blouse. I think I have a Lingerie Lover on my hands, Cindy said with a devilish tone in her voice. In her rubbing she unzipped my pants and found me wearing a pair of pink satin and lace hi-cut bikini panties and a white satin half-slip and matching camisole. It finally happened, a lady has caught me wearing lingerie under my suit. Totally embarrassed, and realizing that my lingerie fetish had been discovered, she helped me out of my embarrassment and tells me she thinks it is very sexy that I like lingerie and it really turns her on that I like wearing it. She asked me if the lingerie I was looking for was really for my sister or were they for me. Blushing, I admitted that I was shopping for me. I told Cindy I only have 2 pair of panties and I was looking something different to wear under my suit everyday. I didn’t have any ideas what to try next. I also admitted that I have had a desire for a lady to help me with these decisions. This delighted Cindy and she went out of her way to help me chose a number of nice things. I love the panties you are wearing they are very sexy.
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But I think I'd like to see you in some different colors. How about a few pastels Cindy says? I like light blues, pinks, aqua, greens, yellows, florals and lavender. I agreed that all those colors sounded wonderful to me. You pick out what you want me to wear I told Cindy. Cindy then confessed to me that it is her fantasy to be with a lady but was afraid, but now that I came into her life she will have the best of both worlds with me dressed in all the soft lingerie as her lesbian lover and my big manly cock to satisfy her manly desires. Cindy picked out a few different matching bras and panty sets in pink, white, including camisoles, chemises, garterbelts, stockings, slips and other things. Then Cindy asks if I would like to see a new article of lingerie that she just got in. I said sure. She unzips her dress and lets it fall around her ankles to reveal stunning lavender satin and lace trimmed teddy with sheer lace-top stockings attached to the garters. What a pretty outfit. She says by the look on my face, I liked it and she has one in my size. Then came my new things; Cindy helped me into my matching set of a aqua colored satin bra & hi-cut bikini panties, white garter belt and lace-top stockings and a beautiful white matching camisole and flowing half-slip. This exited Cindy and we locked into a wet, passionate kiss, and her tongue pulling my tongue into her mouth and sucking on it in a very provocative way. Our hands’ rubbing each other’s body through all the satin that covered our skin. Cindy's hands starting rubbing my cock through my slip over the satin panties I was wearing.
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This feeling brought me very close to having an orgasm and Cindy realized it and raised the hem of my slip and put her head under my slip and began sucking me through my panties. I erupted in my panties and Cindy sucked my cum through the thin satin material covering my cock. Wow! My knees gave out and I slumped to the floor, face to face with Cindy and we locked in a blissful French kiss, and the taste of my cum still warm on her lips was very erotic. Breaking our kiss, I positioned myself under her pussy and she straddled my face. I sucked and licked her pussy through the material of her teddy, already totally soaked from the orgasm she had sucking me off. I needed my tongue inside her now, so I pushed aside the material and drove my tongue in and out of her as deep as I could. No sooner as I sucked her clit into my lips, Cindy moaned and flooded my mouth with her love nectar. This was ecstasy. Cindy regained her senses and mounted my hardened cock. Riding me with her beautiful hair glistening and her tits gliding inside her teddy, I shot of my second load deep inside Cindy, which triggered her third and best orgasm. We collapsed on the floor in each other's arms, kissing and enjoying what just happened. After a few minutes, Cindy and I picked ourselves off the floor, which was covered in many different articles of lingerie, and Cindy insisted I stay with her the remainder of the weekend. I could only say yes and with that she helped me straighten out my new lingerie and she put her dress back on. Turning to me she said, “I can’t have you put your man clothes on over your new outfit. ” With that she tossed me a navy cocktail dress.
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I wasn’t too crazy about the idea but Cindy assured me no one would see you but me, besides I’ve always wanted to do this with a man. So who was I to complain? She helped me zip the back and gave me a pair of pumps to complete the outfit. She even insisted that I put red lipstick on to better kiss her with. I wasn’t too comfortable going in public like this and Cindy just complimented me and kissed me as I drove off. Cindy had me drive downtown and through the park, which was very exhilarating, the entire time her Cindy had her hands under my dress, fondling my cock though my slip, and running down my nylon covered legs and playing with my nipples through my bra. All this rubbing mad us both mad with passion again so I found a dark area of the park, we got out holding each other as close as we could, lowered each others panties, she leaned over a bench and I made love to her from behind. It didn’t take long before I exploded my load deep inside Cindy, which made her cum immediately. We collected our senses, pulled our panties up from our ankles and got back into the car before a cop drove by, went to her apartment where she lead me to her room and threw me back on her bed and crawled up my body kissing her way up my stocking covered legs, satin covered cock pushing the dress I was wearing up and she licked and gently bit my nipples thru my bra and finally to my awaiting lips. After a long sensuous kiss she stood up to excuse herself and lifted me up to unzip the dress. She told me to get comfy and disappeared into her bathroom. I also had to pee and found another restroom in the hall and decided to sit and pee as I always do when I am dressed in my lingerie. I finished up my business and returned to find Cindy exiting her bathroom wearing a black satin bustier with black stockings black heels and a 6-inch thin strap-on cock. I panicked in my mind but found the site of her very intoxicating.
She came up to me and kissed me full on the lips, grinding her crotch into mine. She whispered that I am going to become a woman tonight and gentle laid me on her bed and started kissing her way back up my legs crotch, tits, neck and lips.
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She rolled me onto my stomach and told me to relax and trust her. She promised to be oh so gentle and started massaging my pantied and slip covered ass, moving her hand over and over driving me crazy with anticipation. She lowered my panties and reached over to her nightstand and removed some lubricant and lathered my rosebud virgin ass with the cool slippery stuff. She gently kissed my neck and back as she entered me with one finger loosening her target a little, then 2 fingers went in all the way to the end. She kept her 2 fingers in me moving them in and out slowly reading me for her cock. When she felt I was ready, she moved behind me and applied more lube on her cock and pressed her cock against my ass and it opened up and the tip disappeared into my ass. The feeling was very intense at first but she stopped and applied more lube to ease my discomfort. I found myself pushing against her and finally she thrust and buried her fake cock to the hilt. I about passed out from the sensation but recovered to find Cindy’s hand wrapped around my cock, stroking me as she pumped in and out of my ass. She was really going in and out of me fast now and her strokes were hitting my prostate, which was driving me to an explosive climax. Cindy sensed this, pulled out and told me to get on my back, where she hiked my legs up and over her shoulders and re-entered me where I got a glimpse of her strap-on and it had another end that went into her pussy. Cindy was very close to another orgasm and this made her wild with passion as she grabbed my cock and jacked me off and fucked my ass and I could not hold out any longer and exploded a long stream of jism and Cindy aimed it at her face, then the rest shot out on me, hitting me in the face and finally draining on my chest. Cindy collapsed on the bed next to me, kissing me and the cum on my face, sharing it with me and I licked her cum covered face and shared it with her. My cum was not unpleasant tasting like I thought it would be. We both collected ourselves, undressing each other on the way to her bathroom where we stepped into the shower and cleaned the cum and sweat off each other and kissed even more.
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As we stepped out of the shower, Cindy insisted we put lotion on our skin so we don’t dry out and she had applied a perfumed lotion on us and she said that she wanted me to smell as pretty and the lingerie she had for me to sleep in. She had a surprise for us to sleep in, a pretty pink babydoll nightie and matching panties. We crawled into bed and kissed and fell asleep in each other’s arms. We awaken the next morning cuddling on the couch in our nighties drinking coffee and remembering a night of passion we will never forget. .
