Christine Ch. 01

While in graduate school in New York, I was into BDSM. It was never a lifestyle or an end in itself, it was elaborate foreplay. I did it with girlfriends but mainly I visited the clubs alone after my shift as a waiter. I sometimes played, if the opportunity presented itself, but mainly I watched the action and talked to people.

At time, there were two or three good BDSM clubs which were not for leathermen: Paddles, which started at a very small place in the Village and moved to a much bigger space in midtown on the West Side, and Hellfire, which later became the Vault, in a basement in the Meatpacking District. I could tell stories about them all night, but I don't want to digress.

One Saturday night, I was hanging out at Hellfire when a crowd came in. All were dressed in leather and obviously serious players. Occasionally two middle-class, middle-age couples would go there as "tourists," not serious players, but normally, only couples or single people went, never a big group. I asked someone who they were, and he said they are a club from Washington, DC, called The Black Rose who rent a bus once a year to play at the clubs in New York. Play they did, they were wild.

After grad school, I took a job, my dream job really, in Washington. I didn't know anyone, so I went to the monthly Tuesday Night Black Rose meeting. The meetings were in the basement of a church. They had parties a few times per year, but the rule was you had to attend three meetings and pay nominal dues before you could attend a party. That was to be sure you were serious and keep out the tourists.

At the meetings, new members introduced themselves, plans were discussed for parties, and there were lectures, workshops (like knot tying) and other activities. It was all very mellow, civilized and accepting. Afterwards, some folks would meet down the street at an Italian restaurant for a bite to eat and continue talking. I always went along.

At the Italian restaurant, we had privacy in the upstairs room and sat at a long table. There was an androgynous young woman in transition, only about 19, named Christine. She was tall, thin and African-American of medium complexion. She always wore tight jeans and had a great shape. She always sat across from me.

Christine was evidently very early in her transition but presented as a woman. We'd chat amiably, but she would also wink at me, lick her lips and otherwise flirt. I just assumed she did that with all the guys. At that time, I wasn't attracted to women in transition. I hadn't known any and had never been with one, in the biblical sense. They used to hang out in the back room at Hellfire and give anonymous blow jobs to anyone who wanted one, but they were sleezy and unattractive. It wasn't a very sexy scene.

After waiting three months, I was invited to my first Black Rose Party upstairs in the private room of a gay bar called Badlands. It was a pretty mellow scene compared to the psychosis of the clubs in New York. It was friendly, everyone knew each other. Christine was there. I spoke to a lot of people, just small talk. Then, while I was sitting alone at the bar, Christine walked over with a paddle and asked me to spank her. I was a little self-conscious to play with a woman in transition with a crowd where everyone knew me as straight, but I figured I should be a good sport and in the spirit of things.

She walked over to a wooden x-shaped rack and reached up with her hands facing away from me. She was wearing tight jeans, as usual, and her ass looked fantastic. It was not too small, not too big. It was shaped like two halves of a perfectly bisected honeydew melon.

I hit her on the ass, taking my time between strokes, starting softly and building steadily in strength until she quivered a bit after each hit. She began to gasp a bit when the paddle struck. I rubbed her warm butt between strokes. I whispered, "Let me know when you've had enough." As the strokes got harder, I began whispering, "You look beautiful," "Everyone is looking at you," which was true, and "Your ass looks perfect." She sighed sweetly at each compliment, so only I would hear, sharing those sentiments between us.

After a while she said, "Enough." I lowered her arms and held her. We embraced until the crowd, by then a few dozen people, lost interest and looked away. When she turned around the show was over and the low-keyed party was back in swing.

I offered to buy her a drink and we stood (she was in no condition to sit yet) at the end of the bar away from everyone. I had a beer and she had a bottle of water. "Wow, that was fun. Thank you."

"Thank you," she said.

"You know when you look at me across the table at the restaurant, I always think you just flirt with all the guys like that, but when you asked me to play with you here, I realized it's not all the guys. I think you're really nice, but I must tell you, I've never been with a woman like you before."

"That's alright. I've thought you were cute since I first saw you and thought you'd be nice to know."

"Let me ask you, if it's not too personal, how long have you been in transition?"

"I started dressing in public as soon as I finished high school and started taking hormones soon after that, about two years now. My breasts are growing nicely, I love them. I'd love to show them to you."

"Who do you live with?"

"I rent the downstairs apartment in a house, alone."

"Do you have to be anywhere tomorrow morning? Is anyone going to miss you if you don't go home tonight?"

"No. I don't have anything until the afternoon."

"Well, like I said, I've never been with a woman like you before. If you come over my place, I can't guarantee anything will happen between us. We might just sit around and talk. Do you smoke weed?"

"Yeah, sure."

"OK, but there are four rules: No one does anything they don't want to. We play with safe words. Second, I'm a top, in both senses of the word. Third, if you enter a room with me, you leave with me. Last, no drama, ever. I don't want you calling me drunk in the middle of the night, showing up at my office, making a scene outside my apartment or in public. Do that shit one time and you'll never see or hear from me again."

"OK, or should I say, 'Yes. Master?'"

We left the party without saying good-bye to anyone. I imagined they talked about us hooking up after we left and wondered if this ruined my chances with the women from the club in the future.

No words were spoken as we drove to my place, parked in the garage, went up the elevator and walked down the hall. I don't know what she was thinking. I was titillated with anticipation, not quite knowing what we would do. I had some BDSM equipment in the apartment, but not much and nothing fancy. I knew from previous experience I could always improvise, that's part of the fun.

I opened the door to my studio apartment on a high floor overlooking Route 395 in Shirlington. I closed the door behind us. I took her bag from her hand and dropped it on the floor, pushed her gently against the wall, raised her hands above her head with each of my hands, pinning them to the wall and laid a long, deep, passionate kiss on her. We kissed without coming up for air, pressed together but not too tightly and not grinding. It was all about mouth and holding her against the wall. She was a great kisser.

When we disengaged, I stepped back and said, "Leave your shoes here. Go in the bathroom and take a shower. There is a clean towel on the rack and terrycloth robe behind the door. There should be a new toothbrush under the sink. Take as long as you need but come out completely clean all over and wearing the robe. Have your clothes neatly folded in your arms. In the meanwhile, what would you like to drink? I have beer, white wine, red wine, ginger ale, club soda and a little cognac. Oh yeah, I have tea or coffee too."

"A little white wine would be good." And she went into the bathroom to prepare.

I opened the curtains to the big windows overlooking the highway which looked like a river of light passing by. It was a clear night with lots of stars. There was a half moon and just enough light came into the apartment to see without lamps. I poured two glasses of cold white wine and got out a joint I already had rolled. It was great spanking her in jeans, but bare ass must be even better, although I really had no plan of what to do next. All I knew was that I was very excited. I couldn't wait and took two hits of the joint both to relax and get my creative juices flowing.

I had a restraint set which I had never used. It consisted of nylon straps in the shape of an X which fit under the mattress of the queen size bed and stuck out a few feet at the corners with Velcro cuffs for the wrists and ankles. It wouldn't be too scary for her for a first time. I put it under the mattress while she was in the shower and pulled down the comforter and top sheet. I put on some abstract electronic music very softly.

She came out in the robe holding her neatly folded clothes in her arms in front of her. "Put your clothes on the chair, come over here, sit down, have some wine while I shower. Help yourself to the joint."

I like to take it slowly and deliberately. After shower, I came out in a loose white linen shirt and baggy black linen pants. Christine was sitting on the sofa in the robe sipping her wine, she had smoked some weed. I bent over her and kissed her lightly. "Our safe words are simple and easy to remember. Think of a traffic signal. 'Yellow' means stop what you're doing now or go lighter or slower. 'Red' means end the scene and we stop playing. Now sit up straight and sit forward."

While standing in front of her, I lowered the robe off her shoulders to check out her breasts. They were small, A cups to be sure, with fairly big areolae and nice sized perturbing nipples. They were very feminine. Her nipples were erect. Her glaze was downward. I felt them gently, first cupping them with both hands, then twirling her nipples between my fingers and tugging on them softly. I ran my hands over her shoulders and back. I was exploring and familiarizing myself with her body, which was now mine.

I pulled the robe over her shoulders again, took her by the hand and walked her over to the bed. She saw the restraints and knew what was coming. I piled the two pillows in the middle of the bed, gave her a kiss and told her to unfasten the robe and lie face-down with the pillows under her hips. She did as she was told. "Arrange yourself so your clit is comfortable." I then put her ankles and wrists in the restraints. I put a small pillow from the sofa, the smallest I had, under her collar bone for comfort because I planned to have her in this position for a while. Then, I placed a pair of cheap eyeshades from the airline on her. (OK, give me a break, I wasn't prepared to bring someone home from the party and remember, I had just started my first professional job after grad school, so I didn't have a lot of fancy equipment for this.) I gave her another kiss and whispered, "Remember your safe words. If you feel the urge to come, go ahead, I have another set of sheets, don't mind the mess, let it go. Never hold it back"

In retrospect, I said this because I had no intention to help her get off, never having touch anyone else's before, and her satisfaction would be incidental to mine. I had her keep the robe on when she lay on the bed so I wouldn't see her clit. It being my first time with a woman in transition, I wasn't ready for that yet.

I released one wrist at a time so I could remove the robe and there she was in front of me, completely naked. The bisected melon ass was raised up. Her arms, back and legs were muscular but not manly, more like a woman athlete.

I stood and looked at her for a while feeling high, prepared to follow my instincts. My hesitation built suspense. I sat on the edge of the bed and ran my hands all over her body. When I probed her crack, she grinded the pillows a little. I couldn't help myself, I began kissing and licking every part of her I could reach including the soles of her feet, arm pits and her crack but without touching her pussy with my tongue. She moaned more and more. I began to rub her ass with my hand again and smack! It landed it hard on her right cheek.

She flinched, the game was on. Several more slaps on both cheeks followed. Then I rested. As noted, I didn't have much equipment with which to play but improvisation is part of the fun. There was my belt which I slowly dragged the length of her body, starting at her toes up to her hairline. I then dragged in back and forth across her perfect cheeks a few times before raising it quickly and bringing it down even faster. She flinched and let out a whimper. She must have suspected what was coming when the belt lost contact to be raised.

I spanked both cheeks with the belt several times increasingly hard. She began to moan with each strike. Then I began on her thighs. Then, I pushed her legs further apart to reach her inner thighs. Her butt and thighs were red.

I stopped, sat on the edge of the bed and caressed her ass and thighs with my hand. They felt warm to the touch. I had to kiss them to soothe her. All I could say was, "Good girl."

I probed her crack with my tongue, this time spreading it and running my index finger around her hole. She raised her butt to meet me. I kissed it, then I circled it with my tongue. It was immaculately clean. I was lying on my stomach between her legs with my head buried in her crack and slipped my tongue into her as far as I could. She moaned and writhed. It was pleasurable but I couldn't believe I was doing it. I pulled back and slapped her right cheek as hard as I could. She squealed.

It was time to take it to the next step and satisfy myself with this fine young specimen. I undressed, lay on top of her with my full weight on her and my cock between her warm cheeks. I buried my face into her neck and kissed her shoulders. That alone felt like heaven. With a few grinds, I could have come like that.

I got up from her, stood and struck har ass several more times with the belt, more rapidly than before. She muffled her screams into the bed. Her cheeks had marks from the belt.

After a half dozen smacks, I took a condom and some lube from the night table. (At least I was that much prepared.) I put some lube on my middle finger and slid it into her from behind. I applied more. Then I applied it all over my hard, pulsating cock. I like to apply lube under the condom, it makes it much more comfortable. I put on the condom and a generous amount of lube on the condom.

I lowered myself over her in pushup position and probed her hole with the tip of my sheathed cock. Penetration was slow and deliberate; I didn't know how much she could take. I wanted it to be sensual for her, not uncomfortable or painful. She seemed very accepting.

"I'm all the way."

She hummed and I lowered to my elbows for closer contact and began to stroke and hump her. She rose to meet my strokes. I don't know how long we went on, but I was feeling dizzy. I began to grunt a bit as I pushed harder and she did not object. Finally, I felt the sensation welled up inside me. I buried myself into her as deeply as I could. It felt like falling from an airplane with no parachute. We both shook.

We lay there engaged until our bodies untensed. I withdrew and disposed of the condom while she lay there tied down helplessly, just fucked. I undid the restraints, lay beside her and asked, "Did you come?"

"Yes."

"Good, I'm happy." We kissed. I threw the robe over her and said, "Go in the bathroom and clean up."

She quickly showered and I had fresh sheets out when she returned which she changed while I poured us some ice water and got the joint and lighter. It was late and the room would be flooded with light in the morning, so I closed the curtains.

She lay on her side and I on my back with my arm around her. We were completely nude and quite tired and satisfied. We smoked a little and I asked, "At what point did you come?"

"When you did, we came together...That's a good sign for our first time together. I knew there was a reason I was attracted to you."

I could feel her big, soft, tired clit resting on my left thigh when she swung her leg over mine to come closer, my first contact with it.

"In the morning I'm going to drive you home, after I make you breakfast, after I fuck you."

"Humm." We fell fast asleep.