Satan's Den by jen128

Rating: 92%, Read 30044 times, Posted Oct 27, 2014

Fiction | Anal, Bi-sexual, Consensual Sex, Erotica, First Time, Gay, Hardcore, Oral Sex, Transgendered, Transvestite

It is amazing how a decision or two can change your life completely. I guess I should give you a little background. Two years ago I was a computer technician for a small firm here in town. At 32, with no family and a small apartment it seemed like a dead end.

I did not have a girlfriend and had been with a couple of guys over the years, mainly for a quick blow job or at a glory hole for some satisfaction. I have always been a little small for a guy at about 5'7 and fairly thin. I was told I was too thin at about 130 pounds so most women looked at me as their little brother so it seldom went any further than that.

That fateful Friday night, I had been given a two week vacation. We had been extremely busy and with all of the overtime and accrued vacation the boss insisted that I take at least two weeks to rest up. I had heard of a gay bar on the near west side of town called Satan's Den so I thought why not check it out for some quick relief. Not wanting my car spotted there, I grabbed a bus for the half hour ride to a nearby bus stop and headed over to the lounge. It was a little different with the entrance down a couple of steps and then after through the door continuing down a flight of stairs to a basement. It was a little dark with a dance floor in the center and a U-shaped bar to the side. The music was captivating and the beat almost seemed hypnotic.

I took a seat at the bar and the waitress, with a pretty deep voice for a woman, smiled at me and asked what I would like. With a wink she was off and came back a minute later setting the drink on the bar. When I asked how much, she just said, "Honey. As good as you look I am just going to run a tab for you. Play your cards right and they won't cost you anything." I know the waitress was a crossdresser but she was cute.

I am usually rather shy so I just sat there and nursed my drink while watching many crossdressers both cute and otherwise with guys, some guys with guys and some crossdressers preferring to stay with each other. The music was great and it was fun to watch all of the patrons having a great time.

I was in the middle of my second screwdriver when a nice looking older gentleman asked if he could sit down next to me. As he sat down, all he said for a few minutes was, "Pretty, very pretty." Looking around, I tried to find who he was talking about but he was staring at me. Smiling he said, "I was talking to you. You may not realize it but you would make a very beautiful girl." I sat there for a minute with my mouth open not sure what to say. "I have to say", I said nervously, "I have never heard that line before."

"My name is Richard, but most of my friends call me Dick. I hope you will be one of my friends. I find you extremely attractive", he said very softly. I told him I had always been attracted to older gentlemen. We sat and talked for a while and he bought me a couple more drinks, also taking care of my tab. The more he talked the more I found myself hanging on his every word. His hand first on my knee then caressing my thigh had me swooning. I felt he could tell me to do anything and I would bend over backwards to please him. Was I under some kind of spell? Had he put something in my drink?

He leaned over and whispered in my ear, "I want to take you home with me. Would you do something for me?" "Certainly", I whispered, not even thinking of what it might be. His smile was huge and I saw him motion for a girl that was dancing to join us. That is when he floored me. "This is Debbie", he said. "She runs a beauty shop catering to crossdressers just a couple of doors down. Talking to you and watching your reaction to many things I have said, I believe you would like to see just how beautiful a girl you would make. Debbie takes care of my haircuts and shaves and will do a fantastic job with you. She will bring you back in about two hours, we will dance and I will take a beautiful girl home with me."

I do not know why, but I was speechless. I could not say no to this man. It was like I was under a spell. Debbie took my hand and led me out the door to her salon. As she unlocked the door, she said, "This is extremely private. No one else will know and I think you will be amazed at how much you will embrace your feminine side." I just nodded and followed her blindly into the shop and she secured the door and drew the blinds behind us.

We went into the back in the spa area and she told me to disrobe. She could see that I was hesitant and she explained that she was a cross dresser as well so I had the same equipment as her. Red faced, I removed my shirt, shoes, socks, pants and hesitated at my underwear. Debbie stepped over hooked her fingers in my briefs and pulled them down letting them drop to the floor. That is when she stood back and stared at me. “Richard is going to be very pleased. Beautiful clear white skin and a very nice package. Seven inches or eight?” she asked coyly. “I am not sure but I have never had a complaint”, I said.

Pulling a bottle of lotion off the shelf she squeezed s glob of cream in her hands and started covering me with it from my feet to my waist. I lifted my arms and she coated my underarms then smeared it on my neck and face. “This is a depilatory and will remove the hair. I like that your chest and back is hairless. Your skin is so nice, smooth and soft”. I stood there and she told to wait 15 minutes. When the time was up she had run warm water in the tub and told me to get in and wash up. All of the hair on my legs, crotch and under my arms wiped off and the silkiness of the oils she put in the tub made my skin feel like silk. After about ten minutes I was instructed to get out and towel off.

“OK,” Debbie said. “I have the perfect lingerie for you to put on. But first I want you to rub this lotion all over your body and legs. It will make your skin even softer and silkier and will prevent the hair from growing. On your face as well.” I did as I was instructed then she handed me a garter belt, beautiful silk stockings and a small thong. Having played with lingerie a time or two in private, I knew how to slide the stockings up my legs, smooth them down and fasten the garters. I then pulled on the thong and tucked myself between my legs. “I just love how your pert little nipples are so hard and stand out like they do”, Debbie continued. ”I bet they are really sensitive as well. Here, put on this lightly padded bra and come with me.”

I did as I was told and she had me sit in one of her chairs. “You are so pretty you do not need much makeup but I am going to put mascara, eye shadow, a light foundation, lip liner and some perfect lipstick on you. Then I will style your hair. I love the fact you have let it grow out. After I do your nails and a quick pedicure we will dress you. I know Richard and he is going to fall for you even more than he already has. He has been looking for so long for someone like you”.

When she had finished I had to stand as she found the perfect size scoop necked dress in a feminine pastel yellow. It was sleeveless with and had beautiful lace trim. She slid it over my head letting it fall down around me then zipped up the back. She pulled out a pair of matching 3 inch heels in the same pale pastel yellow as the dress and had me step into them. “I am finished, Candy, now you can look in the mirror. Yes, I will call you Candy just as Dick had whispered to me his pet name for you would be.”

I could not believe the beautiful creature staring back at me. I continued to stare as Debbie just chuckled and said “He told you that he thought you were very pretty. You just had to be shown. Now I need to see if you can walk in those heels and we will head back to the club, I know Dick is anxious to see you.”

She had me practice walking in the heels, learning to take smaller steps for a more feminine walk. She had me practice sitting, standing and talking a little softer like a woman would. We left the salon and after she locked up we headed back to the club. As we walked in, several eyes were on us. A few of the men started to walk toward us then saw Debbie with me. They stopped, smiled and went back to what they were doing. Richard stood and just stared at me. I stopped but Debbie gave me a nudge and told me to walk over to him like I had practiced.

As I approached him he broke out in a broad smile, wrapped his arms around me and gave me a deep big kiss. I wrapped my arms around his neck as my knees grew weak. He pulled me out to the dance floor as a nice slow song began and with his arms around my waist and mine around his neck we danced slowly. I could feel his huge hardon moving against my tummy as we danced and I knew he wanted me. His hands squeezing my ass and running up and down my back sending goose pimples all over me. Kissing me, my neck, my face and staring into my eyes until the song ends.

“I am taking you back to my place. I want you all to myself” said Richard. Once again, there was no protest from me. I still do not know why or how but I seemed to be subject to his every wish. Once outside we found his Escalade. He opened the door for me, helped me in then went around and entered on the driver side. He started the car and we headed out.

“When I saw you enter the club tonight, I felt a very special attraction to you”, he said. “Something inside me told me must have you for as long as you will allow it. Tonight, I am going to show you how much I want you and the pleasure of being my woman, Candy.”

We pulled into the underground parking lot of a large exclusive condo high rise. He parked the car, came around and opened my door and helped me out. He put his arm around me and led me to the elevator. When the doors opened he put in a key and pushed the button for the Penthouse and up we went. His arms around me again kissing me and again I put my arms around his neck feeling so weak just wanting to melt into his arms.

When the doors opened, he scooped me up in his arms like I was weightless and carried me into his beautiful condo. “I want our first night to be so special that you may decide to stay with me for a very long time” Richard said. “I know I am older but can give you everything you want and will take very good care of you.” With that he carried me into his bedroom and carefully placed me on the bed.

“Let me help you with this dress”, he said as he reached behind me and pulled down the zipper. I lifted my arm and he pulled the dress over my head then lay it beside the bed. He gently pushed me back in the bed, his hands on my shoulders, his kisses on my neck. His lips on mine then I felt his tongue exploring as I parted my lips, our tongues entwining, my whole body on fire with desire and my back arching slightly wanting more of him. His hands unfastened my bra and pulled it free. His fingers lightly brushing against my now hard sensitive nipples causing me to moan with the pleasure I was feeling.

He got up for a minute, removed his shirt, shoes, socks and pants. I could not help but gasp at the size of his cock when he removed his briefs. He smiled and whispered that I need not worry. He was going to be gentle. He was back at my side and I could feel his hard cock against my leg. His tongue and lips went to my one nipple lightly flicking across is then sucking. His one hand again playing with my other nipple and my whole body shivered from the pleasure. His free hand he put between my thighs, stroking them through my stockings and worked his way up to my crotch. I felt a finger push through my tight little hole and gasped. The combination of his attention to my nipples and my ass was incredible making me almost cum. He then pushed a second finger in then a third. “I know it hurt a little, my darling, but it will subside quickly and will feel more incredible than anything you have experienced” he said. I was panting as I said, “Oh Richard, I have never had anything in there, fingers or anything else.” “My dearest little virgin”, he said, “I will be gentle and make a woman of you tonight. And, please call me Daddy.”

I did not understand but his wish was once again my command. “Yes daddy, I want to please you as you are now pleasing me.” With that, he trailed his kisses down between my breasts to my tummy and then he took what he called my clit into his mouth, The feel of his mouth on me and his fingers caused me to explode into his mouth. He continued sucking until he had drained me then began licking and kissing between my thighs. He kissed my ass then his tongue began darting into me. I arched my back and cried out “Oh my gawd, Daddy, that feels so wonderful!!” He continued tongue fucking me for a minute then his kisses trailed down my inner thigh to my ankle then back up my other leg.

Next he picked me up and slid a pillow under my ass for better access. I felt his fingers enter me again with some type of lubricant. He moved up, his hips spreading my legs wider until I felt the tip of his large cock pushing lightly trying to enter. He told me to relax and as I did I felt the head of his cock enter me. I cried out ion pain and he leaned down to kiss me. “It will subside quickly, my little girl, then it will be more pleasurable than you could imagine”. The pain did start to lessen and I felt his cock slowly being pushed into me, inch by inch. Stretching me as I felt every vein, every ridge of his hard thick cock as it pushed deeper. When I felt his balls against my ass he stopped and held it there. It felt as if he were almost in my throat.

As he began slowly moving in and out he also leaned down sucking on my nipples and kissing me as he fucked. The pain went away completely and I found myself lifting my hips to meet each stroke not wanting to feel the emptiness as he withdrew. The feeling was more incredible that anything I had ever felt and found myself cumming again. I had never cum more than once before and his continuing motion in and out was keeping me on that high. I could not stop moaning and pleading for him to continue. His intensity increased and suddenly he rammed his cock deep inside me, his balls smacking against my ass when I felt his cock pulsing as he started shooting and twitching. I could not believe it but I started cumming one more time as I felt his hot thick cum gushing inside me. It was unbelievable. He collapsed on me and I wrapped my legs around him to hold him inside of me.

I was panting and still on a high I had never felt before when daddy, or Dick, started kissing me again telling me how wonderful, hot and sexy I was. “I have never felt like this”, I said, “It is so incredible I cannot describe it. You were right, your little girl’s pussy could not get enough of that big wonderful cock of yours.”

He winked at me and said, “So, does that mean you will stick around for a while? I have so much yet to teach my little girl.” “Oh yes”, I cried, “as long as you want me, I am yours. Teach me whatever you want and use me however you want. I am now your sex and love slave.”

He rolled off of me as his cock finally shrunk and came out with a pop. He took me in his arms and kissed me again. “I will take you as far as you want to go and maybe further”, he said as he smiled and I fell asleep in his strong arms.

(Perhaps a Part 2 later?)

Rating: 92%, Read 30044 times, Posted Oct 27, 2014

Fiction | Anal, Bi-sexual, Consensual Sex, Erotica, First Time, Gay, Hardcore, Oral Sex, Transgendered, Transvestite


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