This story takes place about 12-15 years ago. I was living in southern Connecticut at the time and had a nice apartment close to the Metro North line which could take me into Manhattan and all of its delightful culture, cuisine, and debauchery. I had experienced a dry spell and hadn't been with a man for some time, so I decided to join an alternative website that was open to crossdressers. I had some photos taken in my femme form and uploaded some of the better ones, making the ones of my face private. I put in the profile that I lived in Manhattan so that I could protect my privacy. After writing up my profile stating that I was looking for men, women, trans, and CD partners, I made the profile live and waited to see if anyone would respond.

Surprisingly, it didn't take long for interest to come in, including a nice young man named Michael who was cute and not pushy or crude at all. In fact, he came across as quite the gentleman. And he was tall at 6'4", which was a good thing as I am 6'0" tall without my high heels - and I am never without my high heels! He lived in Manhattan, which was ideal in that he was close enough to meet up with but not too close to my actual home. We began chatting quite often over a two- or three-week period and were contemplating meeting up in person.

About the same time, I got a message from a profile that informed me of a Trans/CD party coming up on Saturday in Manhattan. Men paid $100 to get in, and the girls got in for free. It was BYOB, and there would be security at the door. I replied that I was interested in attending, and they promptly sent me the address of the loft where the event was to be held. The message told me that my profile name would be at the door. I received another message with the rules of play: there would be semi-private and public areas, play is optional, watching is acceptable, consent is a requirement, "no" means "no", condoms for penetration, no drugs (including poppers), and a few others that I also supported.

By coincidence, that same day, Michael sent me a message telling me about the Trans/CD party and asking me if I was interested in meeting him there. I said 'yes' and it was a date!

On the day of the event, I checked into a Marriott property near the loft on the East Side in Midtown. The event started at 9:00 p.m. and ended at 4:00 a.m. There were no Metro North trains that ran that late at night (or early in the morning, if you wish), and I didn't want to drive at that hour. Also, if Michael and I hit it off and wanted some true privacy, we could head to the hotel. I checked in about 4:00 p.m. and took a long, luxurious bath. I shaved, applying lotion on my legs, ass, and privates. Luckily, I have very little to no body hair and keep my facial hair and crotch hair under control with regular hair removal creme for a silky-smooth touch.

After the bath, I took out the tweezers and shaped my eyebrows, then applied my makeup. I was going for a sultry look with shades of grey eyeshadow, fine liquid eyeliner, and of course long false eyelashes. I applied a modest amount of blush and a medium red lipstick that would match well with the purple satin blouse I had selected. I then glued my Aphrodite D-cup breast forms on. I applied latex to blend in the edges, making them virtually disappear.

I keep my fingernails quite long for a man, but I decided to go with longer acrylic fingernails for the occasion - a long almond shape. I used a polish on my fingers and toes that matched my lipstick. I spent quite a bit of time getting my auburn wig on and styled just right. It had long bangs, came down just past my shoulders, and the color really made my green eyes pop.

I am a lover of lingerie, so I put on a black lace open-crotch corselet with garters and black, seamed, Cuban heel stockings. Next was the purple satin blouse with 3/4 sleeves, and a gaff to keep my boybits tucked smoothly away. (I am a grower, not a show-er, my clitty is cut, 7 1'2" long, and slender with a slight upward curve.) Next was a black, micro mini skater skirt, followed by a black leather, over bust corset. I finished off the look with black d'Orsay peep-toe pumps with a 4" heel, an array of gold bracelets, and large, gold hoop earrings. I grabbed the split of Veuve Clicquot I brought for the event, as well as my black clutch. I double-checked the clutch to make sure it was packed with cash, my cellphone, my room key card, lipstick, blush, a variety of condoms, and lube.

I felt sexy, but the look was a bit too slutty for public consumption, so I wore a mid-knee-length, black, lightweight overcoat down the hall, down the elevator, and out to the street. I grabbed a cab and headed to the loft. It was 9:15 p.m. so I would be fashionably late. The old building was quite unassuming, and I was a bit nervous about it, but I hit the buzzer for the 5th floor, gave them my name, and was let in the building. After a noisy ride in a typical old, small, musty Manhattan elevator I stepped into the lounge area of the loft where I was greeted by Nate, a handsome black man about 50 years old with a fit figure in his Chinos and Polo shirt.

"Welcome, Diana. I'll take your coat, and you can check your champagne in at the bar. You know the rules, so enjoy yourself."

I gave him a kiss on the cheek, handed him my coat, and checked in my champagne, but not without asking the bartender to open the bottle and pour me a glass. She was happy to do so, and I tipped her well, hoping she would remember and take care of me. She smiled and we exchanged kisses on the cheek. I turned to take a tour of the loft, soaking in the environment. The lounge was filled with a couple of sofas, a padded bench, and two overstuffed chairs, all in leather. There were black curtains hanging in the loft, dividing it into small rooms where there were overstuffed leather chairs, or a leather cushioned bench, or a leather sofa, or a bed. Soft lights were draped along the top of the curtains that created enough light to see by, but kept things a blend of mysterious, and a bit romantic even. The space was tastefully done and felt very clean.

When I walked back out to the lounge area Michael was standing next to Nate, paying the entry fee. I walked up to him, and he recognized me immediately. We hugged and looked around the lounge area for a place to sit, but a lot of people had arrived during my short tour, so we walked back to the curtained area and found a bench in a 'hallway' area and sat to talk. He was as cute in real life as he was in photos, and I hoped he felt the same about me. We chatted briefly, and then he lowered his head and came in for a kiss.

It was soft and tender, and his skilled tongue tasted delicious. Our kiss became more passionate, and his hands were all over my back and ass. I placed my champagne glass on the floor, pulled him toward me, and then explored his firm, well-built chest. He obviously spent some time at the gym! His arms were firm and larger than I thought they would be from the photos. As he wrapped his hands around my waist, my hands had fallen to his thighs. We never broke the kiss, our tongues entwined, exploring each other. People were walking by to go to the rooms, so Michael finally broke the kiss and said, "Perhaps we should get a room before they are all taken."

I nodded approval and picked up my champagne. He stood, taking my hand ever so gently as we walked around the loft in search of a little semi-privacy. He led the way, bypassing the rooms with the beds and settling for a room with a leather sofa. We sat on the sofa; I placed my drink on the end table, and immediately resumed our kiss, our hands exploring each other's bodies. My clitty was straining at the gaff as my hand found his crotch. He felt well-hung and was hard as steel. I unbuckled his belt, unfastened his trousers, and unzipped them without breaking from the kiss. He was such a great kisser!

As I took his cock from his trousers—he was going commando—I guessed it was 7 or 7 1/2 inches long, cut, and very girthy. I unbuttoned his shirt with one hand and was kissing my way down his chest as I stroked his wonderful cock with the other hand. I leaned in and took the head in my mouth, circling my tongue over the head, paying particular attention to the underside of the glans. I heard footsteps in the room as I tried to take the full length of his very thick cock in my mouth. I began pumping up and down the shaft, my tongue extended in an effort to get all of him in my mouth and down my throat. But he was just too thick, despite my best efforts. I made passionate love to his cock with my lips and tongue. His hands were massaging my back and ass as I sucked his cock, making my boipussy ache with need.

As I slid off his cock to say something to him about the need I felt, I noticed the 3 or 4 guys who were standing off to the side watching me suck his cock. They were subtle, standing off in the shadows, and I gave them little mind as watching was permitted, after all. I thought about it for a moment and then thought, 'What the hell', whispering, "Would you mind putting on a condom and fucking me long, hard, and deep?"

He held out his hand as if to say, 'Hand me a condom,' so I reached in my clutch and pulled out a Magnum to accommodate his girth. As he put on the condom, I stood and removed my gaff, placing it on my clutch. I took the lube and gave my boipussy a thorough lubing. After turning to have my ass face him, I bent my knees, leaned over at the waist, and reached down to grab my ankles, beckoning him to take me. His hands put a firm grip on my hips, steadying me in that pose, and slowly he began entering me. I closed my eyes in ecstasy as I felt every inch of his length and girth pressing against my P-spot. Precum quickly formed at the end of my clitty and, in a long stream, began pooling on the floor. When I felt his balls against my ass, I opened my eyes. What I saw was quite a sight to behold indeed.

Nate was standing in front of me with his uncut 9- or 10-inch cock out of his Chinos, stroking it inches from my face. The watchers in the room all had their cocks out, stroking them slowly as Michael pulled out to the tip, only to bury his cock inside me again, his balls once again slapping on my ass. One of the men watching us moved to my right side, his 6-inch uncut cock firmly in his grip. A young black man with a cut 8-inch cock moved to my left side. I looked back at Michael with a bit of concern in my eyes, and he just smiled a huge smile and nodded his head enthusiastically.

Taking this as his cue that his feelings would not be hurt, I turned my head forward, grabbed Nate's beautiful, huge cock in my right hand, and pulled him toward my mouth. I reached out with my left hand and took that lovely 8-inch black cock in my grasp and began stroking it. With Nate's huge cock firmly in my lips, I let go and grasped the 6-inch cock to my right and began stroking it as well.

Michael began fucking me with more force and speed, pushing Nate's cock deep in my mouth and throat. My hands were covered in precum from the stroking I was giving the two former watchers. I glanced over at the line of men standing there stroking. The room was filled with the delightful scent of musky men, which did nothing but heighten my experience, driving me mad with desire. One of the men slid under me, taking the head of my clitty in his mouth, sucking the stream from me as Michael pounded me with that thick cock of his. I gently pushed his lips away from my clitty head so I wouldn't cum too quickly. He stayed beneath me, drinking my precum as if my clitty was a fountain.

Nate's shaved cock was so smooth and soft and delicious, his foreskin a delight, my tongue swirling around the head on the out stroke as Michael's pumping forced Nate to skull fuck me with that magnificent big black cock of his. Time passed in a most surreal fashion as my red-tipped hands pumped hard cocks, my mouth treated to a beautiful cock, and I was being masterfully fucked by my date. After an unknown amount of time, I could feel that Michael was close to cumming as his pumping was reaching a fervor pace. I then felt his cock throb and pulse as he filled the condom with rope after rope of cum, slamming into me as each rope left his cock. It seemed like he would never stop cumming. He stayed buried to the hilt inside me, basking in the afterglow for a time. He then pulled out and sat down on the sofa to watch.

Nate pulled out of my mouth and walked behind me. After a brief delay to put on a condom, I felt him begin to enter me with that magnificent cock of his. I pulled the man in my right hand around to my face and engulfed his cock in my mouth, balls deep, crying out in ecstasy over it as Nate filled me with his full length. He began pounding me balls deep with a maddening pace as one of the watchers walked over, placing his hard, pre-cum-soaked cock in my right hand. I was stroking in rhythm to the fucking I was getting as I deep-throated the man in front of me. The cock in my right hand was of average length and girth, shaven smooth with huge balls. The long, black cock in my left hand was soaked with precum and close to cumming.

The one in my throat didn't last long, and he warned me that he was about to cum. I nodded my head in approval and moments later the first of many ropes of cum began shooting down my throat. He filled my mouth with a creamy, sweet and salty reward that I eagerly swallowed. As I cleaned off his cock with my tongue, I pulled the cock in my left hand around to the front and slid him into my hungry mouth as Nate continued pounding my boipussy, causing me to me to sissygasm into the awaiting mouth beneath me. Cum poured from me in long, steady streams, my body convulsing with pleasure, my legs quivering with delight.

With my left hand now empty, I motioned to the group of watchers/strokers and one of them walked over to fill my hand with his hard 7-incher. Fully loaded with cock I once again, I was over-loaded with male delight. Time was once again a surreal state as I was cock bound and loving it. Nate was picking up his speed and pounding me harder, so I knew he was close to cumming, as was the young man in my mouth, so I pulled my mouth of his cock momentarily and called out, saying, "You two cum at the same time - drill me and fill me!"

They took the cue and began sawing back and forth down my throat and in my ass in a fevered pitch. I felt Nate pulsing in my boipussy as the first rope of cum shot down my throat. He filled my mouth with another tasty treat as Nate's cock throbbed and pulsed, filling the condom as well. As the cock in my mouth pulled out, I swallowed once again and pulled both cocks in my hands around in front of me, placing the heads of both cocks in my mouth at once. I began pumping their cocks faster as my tongue ran over their glans. In just a few minutes I was once again rewarded with a delicious double load treat of cum. I let it sit in my mouth for a time, letting it coat my tongue and cheeks before swallowing it down. Oh, how I do love the taste of cum!

My legs were shaking from exhaustion, and I could barely stand. Michael helped stand me up and then guided me down onto the sofa. Nate appeared with a fresh glass of champagne, handing it to me with a broad grin on his face, mouthing 'Thank you' before walking away. I was thoroughly spent, having swallowed four loads of divine spunk and getting fucked long, hard, and deep twice in a row. After finishing the champagne, I put my gaff back on, and Michael helped me to my feet. We exchanged phone numbers on the way down the elevator, and he waited with me as I hailed a cab. We kissed goodnight and made plans to get together just the two of us the following weekend. I returned to my hotel satisfied and exhausted.