A Man Named Candy
by Dickcy
Last year, near the end of October, I had a date to meet a girlfriend of mine in a Bar in San Francisco after work near Market Street. She was about an hour late and as you might imagine, an hour of sitting on a barstool doing what people do on barstools resulted in me being a little tipsy and a bit irritable. In hindsite, her being tied up at work was a reasonable excuse, but she could have called to let me know. Our resulting impatience with each other resulted in Suzy leaving and me staying on the barstool alone.
After another few drinks which did its additional damage, I left and wandered up some of the side streets in an area I didn't know very well. I found a bar which had some bright pink lights in front and stopped for another drink. I was a little angry and a lot lonely and pretty drunk all at the same time. I really didn't look around much and stared at my gin and tonic as I drained the glass a little at a time and ordered another. Suddenly a hand started to rub my neck and I got jerked back as close to reality as was possible in my condition. The hand was strong and soothing and I turned slightly to see who to thank.
I was pleasantly surprised to see the hand belonged to an attractive black lady, about 30 years old with silky ebony skin and large smiling brown eyes. I smiled, told her it felt good and turned my head back forward and relaxed. Not another word was spoken for a few minutes as her strong hands rubbed and massaged the back of my neck and I just enjoyed. After about 5 minutes, I turned to the woman pampering me and introduced myself. I was ripe for the plucking and this sexy lady knew just how to take control.
Her name was Alicia and she lived a few blocks away. I offered her a drink and she slid next to me on the barstool accepting my offer. She didn't drink much, but I continued at a slow but steady pace and Alicia and I talked for hours. Actually, Alicia mostly listened and I talked. A couple of times I asked her to dance and was surprised when I stood up to take her hand that she was several inches taller than me although perfectly proportioned. She had long black eyelashes and long thin painted fingernails and sensuous red lips. When we danced, my coordination was poor and I was pleasantly surprised at how graceful Alicia was and how she was able to lead when I failed to keep control. I was clearly under the influence and typical male, I used the slow dances to feel her body and butt through her silky short tight dress as we moved across the floor. She did nothing to stop me and rested her head on my shoulder.
As the evening passed, I rambled on about my lack of lovelife and like any drunk at a bar found myself more and more attracted to the lady sitting next to me. She was beautiful, but I wouldn't normally have been in the neighborhood and really had never dated any black women. As the drinking hours started to draw to a close, I began to hit on Alicia more and more, rubbing her leg and complimenting her on her looks and charm. Finally, advancing from small pecks on her cheek, to pecks on her lips, to long sucking kisses. Alicia led me on and I became more and more attracted to the point where I asked her to come home with me when the bar closed at 2:00. I could hardly walk, much less drive and it took very little for us to settle on her place. Alicia led me to her 2nd story apartment which was modest but well furnished. When we got inside I collapsed on her sofa and Alicia helped me out of my jacket, tie and shoes. Alicia sat next to me and we necked for a while. She unzipped my fly and pulled out my limp penis as I sucked hungrily on her lips and ample breasts. I was took drunk to get hard and as the realization came to me I felt guilty at not being able to provide Alicia with the sexual satisfaction I could tell she wanted as much as I did.
She told me not to worry about it, that she enjoyed my company and she knew the night would be rewarding for her. I had no idea what she meant, but the pride at being in the arms of a woman of her beauty kept me happy. Finally, Alicia undressed me totally and left me on the couch while she ran bathwater for me. When she came back, she had changed into a white silky nightgown with a matching silk robe, and she still wore her black nylons and garters and high heels from earlier in the evening. She led me to the bathtub and put me in the warm water. She told me to relax which I did, actually falling asleep part of the time and Alicia rubbed my entire body with a sweet smelling liquid soap, lathering my still limp cock much of the time. She gently rolled me to one side, exposing my rear end and as I lay back relaxed with my eyes closed, I tensed up suddenly as she progressed from gently rubbing perfumed soap up and down my rear crack, to using the soap for lubrication and slipping a couple of those long black loving fingers deep into my dialated hole. It happened so fast I had no defense and I was too drunk to resist. As Alicia increased the amount of soap and the reaming pumping activity of her fingers in my asshole, I moaned and again relaxed enjoying the new sensation from the place I'd never been touched.
After about ten minutes of this type of play, I became a little more alert and Alicia helped me from the tub. She helped me dry off. I felt so loved and pampered that I was continually french kissing Alicia and thanking her for taking such good care of me. I sensed she was hot and I felt impotent for not being able to play to big cocked macho male for her. Alicia didn't seem to mind and we agreed to lay down and just go to sleep. I was cold and we couldn't really find anything for me to wear. I don't exactly know how it happened, but the next thing I know, I'm wearing a silky black nightgown cut up the side almost to the waist and I'm slipping under the covers. The feminine attire rubbed sexily against my body and I felt Alicia slip into bed next to me putting her hand on my silk covered cock. She lay against me sucking on my tongue and rubbing her hand over my body, but my limp dick would not respond. We both laughed a little and Alicia rolled me on my stomach for a little more play. She began to tell me I had a cute ass and the next thing I know, as I lay in my stupor, Alicia is massaging my rear end. At first it was gently through the silky gown causing me to wiggle sexily in response, but then she got more serious and pulled up the back of my gown exposing my anus. She put a couple of pillows under my midsection and opened her nightstand drawer obtaining some KY Jelly. I wasn't alert enough to catch on and before I could react, Alicia had lubricated my ass liberally and began again working her fingers in and out, slowly at first and then more aggressively as the minutes passed. She turned out the lights and moaned as she worked at my liberally greased anus with her hands. I was practically asleep and never even felt the change until it was too late. Suddenly I noticed that the fingers were much fatter and longer and I felt a stretching of my already dialated asshole. This new assault felt wonderful and hurt a little at the same time. It never occurred to me what was actually happening and I reached back with my hands to spread my hole a little wider to reduce the feeling of being stretched. Alicia started pumping harder at my creamy white ass which was sticking up in the air with my hands spreading the cheeks. When I felt Alicia's loins banging against my soft asscheeks I suddenly became alert enough to realize something was wrong. I start to try to get up but Alicia's strong hands pinned my arms as her body pumped vigorously at my rear end. I could only hope it was a dildoe and went into total shock as Alicia's pumping slowed and I felt a load of hot wet liquid squirt into my ass as Alicia tensed, then relaxed, then layed limply on top of me.
Alicia's tongue worked in and out of my ear and neck as she thanked me for providing her the sexual gratification. I was shocked, ashamed and sexually aroused all at the same time. Now I realized Alicia was transsexual. I was laying in her bed dressed as a woman, and had provided her with the "pussy" she needed for satisfaction. At the same time I had never beed fucked in the ass before and I had the same feeling of regret and violation that any virgin would have. My ass felt wonderful and loved on one hand, and I could feel Alicia's love juices running between my legs, but at the same time I was in shock as that is not the sexual role I was used to playing. Before this realization that I had been the female sexual partner, I had gotten to be very fond of Alicia and could picture myself asking her to be a part of my life. What do I do now? As Alicia's fingers began to rub on the slippery liquid oozing from the crack of my ass, I began to protest. My complaints were rudely interrupted as she thrust her sexy long fingers covered with the salty slippery liquid from my rear end into my mouth. I tried to resist momentarily, then resigned myself to sucking on her fingers and trying to get over the shock of what had been done to me. Alicia pulled her fingers out of my mouth and returned them several times as my thought drifted off into space.
Alicia finally pulled the nightgown down over my ass, removed the pillows under my mid-section and rolled me over instantly covering my mouth with warm wet sucking kisses and falling asleep in my arms. I was too tired and drunk to do anything but wrap my arm around Alicia and go to sleep myself.
I slept soundly and awoke slowly in the morning with a bright ray of sun shining in my eyes through the drapes. As my eyes opened and began to focus, I remembered what the night before had done to me and I felt like it was a dream. I spun my head to the side expecting to see an empty bed and I would know it had been a dream, and to my joy and horror both, there slept Alicia.
My movement caused Alicia to wake up and as she saw my face, she smiled and leaned over to plant a wet kiss on my lips. Her arms grabbed me around my waist and pulled me next to her in the bed. This movement of my body caused my silky gown to rub on my body and I was reminded of my silk nightgown attire. I relaxed and let Alicia pull me next to her and reached slowly with my hand to her crotch to assure myself that this foxy lady was indeed a woman. As my hand found its place to nestle into the warmth between Alicia's legs, she moaned and I was shocked as I wrapped my fingers around the largest cock I had ever even imagined. It was thick and long and responded immediately to my touch.
I had no intention of stimulating new sexual activity, but obviously Alicia had other ideas. She pulled me to her tighter and opened her mouth fully as she locked her lips against mine. I started to resist, but as the futility of holding her off became apparent, I relaxed and opened my mouth allowing her pink moist tongue to probe the depths of my mouth freely. Her hands rubbed gently over my silk covered breasts and cock and I shamefully could not stop myself from sexual arousal. I began to suck back and moved my hand back over her huge protrusion. After 5 full minutes of being locked in a kiss, my face was gently pushed down to Alicia's breasts and I gently sucked each of them like a baby. Alicia gently rubbed the back of my neck with one hand and my silk cover penis with the other. Slowly she pressured my head from her ample breasts to her belly and as I spread wet slippery kisses over her belly, she pressured my head just a little lower. Suddenly my mouth hit her pubic hair and the warmth of her large cock pressed against the side of my face. I turned to look at Alicia's love pole and felt my face flush as I saw it for the first time. This sensuous lovely feminine creature had a cock that was at least 11" and hard as a rock.
In horror I pulled my face away and up from under the covers and looked at Alicia's smiling beautiful face. My face was bright red and I for the first time had to face the reality of the night before. I wanted to believe I had been raped to preserve my masculinity, but I could not help but recall my hands grabbing my rear cheeks and pulling them apart for Alicia to have full and unencubered access. Only I knew that my expectation of that moment never considered that it was a real cock fucking my virgin asshole.
In fact, until now I really never though of the experience as anything other than extasy provided by a beautiful sexy lady. I started to say something but could only stutter. Alicia's face turned from a happy grin to her own look of sympathy as for the first time she realized that I did not suspect her of being transsexual. She too was flustered and appologized repeatedly saying she though for sure I knew. Her hand began to sympathetically rub my ass and her sincerity was obvious. We stared in each others eyes for a few minutes and Alicia broke the silence by saying that she was sorry I didn't know but that I was very handsome and satisfying for her and she thanked me. I shamefully forgave her and expressed that it was my own fault, admitting that at the time it felt wonderful. I hung my head in shame and told Alicia that she had taken a "cherry". She pulled my head down between her ample breasts and hugged me tightly, rubbing the back of my neck. She whispered sweetly that to have been the one to have had my sweet white pussy first was an honor for her she would cherish, finishing with multiple compliments about how good it had been for her and how she couldn't resist
Alicia then professed embarrassment at finding that I did not know what was happening and told me to get up and leave if I wanted. Half of me knew I should get up and get the hell out of there, but the other half was wearing a woman's gown and was enjoying having my head and neck stroked. I made no attempt to get up and responded by opening my mouth and sucking hungrily on Alicia's ample breasts. As I continued to suck gently, I felt Alicia's large cock pulsate and grow and push against my silk covered thigh.
Alicia took my hand and placed it around her meat and then she held me tight. We lay together comfortably, not a word said by either of us. Alicia's cock remained hard and after a few minutes I began to pump my hand gently in and out and Alicia put her tongue in my ear in response. I could feel her breathing quicken in my ear and I could feel the tension in her cock as it glided along the palm of my hand. I felt Alicia's free hand applying KY Jelly to my rear hole and suddenly with no notice, Alicia pulled back and flipped me over in the bed and spread my asscheeks with her slender black fingers. She grabbed me by the waist and pulled me to her backwards, pressing her cockhead against my well lubricated anus. This time I wasn't drunk and the tight stretching of my inexperienced hole made me yell as my sphincter gave way and the massive black cock glided smoothly into my pussy. The silky gown rubbing on my skin and the arousal I felt before I was attacked caused me to have an almost instant orgasm when combined with the sexual feeling in my anus. Alicia's hands were on my cock and she took the creamy liquid and rubbed it in my face and mouth as she moved smoothly and gently in and out of me. She was clearly experienced and was making love to me trying to cause me as little pain as possible. I was used to stopping lovemaking after I came, but in this case it wasn't up to me and the loving asssault on my male "pussy" continued.
Alicia asked if I wanted her to stop and I wanted to scream "yes" but the words wouldn't come out of me. I struggled, but Alicia was stronger and excited me more as she slapped my ass hard and told me to relax. After several minutes I felt powerless and relaxed my mind and my sphincter and decided to accept Alicia's love. I put my hands on my asscheeks as I had done the night before, spread myself as wide as possible and told Alicia that I was hers. I think thats all she wanted to hear, because no soon had the words passed my lips and Alicia tensed, screamed that she loved fucking me in my male cunt and shot a huge load of cum into my sucking receptical. I was exhausted and could feel the slime of come, KY Jelly and my anal juices running between my legs onto my balls. Alicia again flipped me over, sliding up my body and slid her slippery massive cock between my moist lips. I had no strength to resist. I had never had a cock in my mouth before and to start with one covered with all these anal juices would not have been my choice, but I had none and I knew what was expected of me instinctively. To resist was not possible and I used my tongue to lick, suck and kiss the huge black raping tool. I couldn't blame anything on alcohol this time, I was sucking, licking and loving Alicia willingly and the smile on her face and the love in her eyes let me know the joy I was giving her.
Alicia finally relaxed and withdrew her tool from my mouth and lay down next to me on the bed. We put our arms around each other and fell into a mutual deep sleep. When my eyes opened, hours later, Alicia was silently laying next to me with her eyes open stareing into my face. As my eyes fluttered open, she smiled and kissed me firmly on the lips. By now it was late afternoon, and Alicia got out of bed and set my clothes neatly on the chair next to the bed asking if I wanted to go home. She gave me her hand and helped me up from her lair and looked me over with a smile, moving her hand gently over my silk covered body. She helped me slip the gown over my head leaving me naked in front of her. I shamefully walked toward the bathroom to take a shower and was disappointed that Alicia didn't follow me. I took a long hot shower and as I stepped out, Alicia came into the bathroom with a large towel and dried me off. I got dressed slowly with mixed emotions and not a word passed between us. As I opened the door to leave, Alicia gently placed her hand on my arm and asked if she would ever see me again. I didn't answer in words, but I put my lips against Alicia's and opened my mouth allowing her to suck again on my tongue as she had done several times the night before. Alicia gave me a piece of paper with her phone number on it and I headed down the street past the bar of the night before to find my car. I carefully folded the paper Alicia gave me and placed it in my wallet as I knew I would use it again.