First Time


I'll start with a description. I'm 46 years old 6' tall and fairly thin. Oh and I'm a cross-dresser that when dressed goes by Lisa. I have been for years. Don't know why other than it pleases me. I love the feel of stockings and garters and for a few years now have gotten to where I enjoy having a nice thick dildo in my rear. I've fantasized of the real thing for years but haven't tried it yet. Until now.

I placed an ad on a web site for a likely candidate. Many men expressed interest, some agreed to meet and after many, many attempts not one man showed up. I wish they knew the effort and work that we go through.

I ended up chatting with two other cross-dressers and they had experienced the same problem. We decided to rent a hotel room and each invite two other men as dates. If none of our dates showed up, we "girls" would entertain ourselves.

As our date night approached I used hair removal cream and a razor to remove all body hair and oiled myself for several days to make my skin silky smooth. On Saturday morning Jan one of the girls and I met in the room and cleaned each other numerous times, inside and out. We applied makeup to each other, on the light and subtle side but enough to show that we had definite feminine features.

Robin, the other cross-dresser that was to meet us called saying she was unable to make it. She also said she'd been unable to reach her dates and that they may show up. Jan and I decided to go on as planned. We began dress in our outfits. Jan wore a heavily boned white corset with shear white lace top stockings and 4" slip on heels with a shoulder length, flirty reddish blonde wig.

I wore a black waist cinching corset that Jan had to help me cinch and she pulled it extremely tight. It had a shear, sleeveless top that had a tight collar around my neck. I had D-cup breast inserts in a clear poly bra under the shear top of my corset. My breasts had prominent nipples and where actually a squishy rubbery exterior with a heavy fluid filled interior cavity giving them major bounce and wiggle. The shear top gave them a subtle yet shiny appearance.

Attached to six garter straps I had coffee colored, full fashioned, seamed stockings. I wore a long blonde wavy wig and perched myself on 6" black stiletto heels with buckles around my ankles. I found walking somewhat difficult but I suspected I wouldn't be walking much.

At 5 till 6 there was a knock at the door. Ron one of Jan's men arrived. Jan and I had not gotten all gussied up for nothing after all. He was gushing with compliments about our looks and his luck. Soon the knocks came again from the door. Walt, one of Robin's men, an attractive black man, something I hadn't considered but found appealing, appeared and Tim one of my dates arrived. We all had a glass of wine and Jan and I were continuously complimented. We discussed the rules, condoms were a must and no meant no.

Shortly Mike, Jan's other date arrived as well as Jack, Robin's other date, also black. Robin obviously preferred black men. Sam, my other date arrived, bringing two brothers Ron and Larry along as well. Feeling overwhelmed I was also giddy with excitement. We couldn't get any willing men to appear and now Jan and I had eight before us.

Some of the men began undressing while some began fondling us. Jan was picked up and placed on one of the beds. I lost sight of her at this point as I was picked up and laid on a padded foot stool. My head hung off one side and my rear off the other.

Sam swung his penis in front of my face. Instinctively I engulfed his cock, sucking as forcefully as I could, trying to insert it as deeply as I could. I had yearned for this for so long I vigorously attacked it while paying close attention to my technique. Lubricated fingers probed and stretched my rear entrance while unseen hands held my legs up and apart. Soon I felt nudging from what I knew was my first cock. I lifted my rear, attempting to gain entry. I heard several comments about my slutty behavior which only excited me further. The owner of the invading cock finally granted my wish and began a slow but relentless push. Never stopping or slowing for adjustment. The incredible feeling of fullness and knowledge that a real blood pumping, semen shooting penis was wedged in me had my own penis pointing skyward.

I knew when his pelvic bone mashed my testicles that I was fully impaled on my first cock. The owner began slowly but built to a hard pounding flesh on flesh fucking that shook my whole body. My wiggling, jiggling breasts were in perpetual motion. Trying to give a first rate blow job upside down and with the my body shaking with each thrust was impossible so I simply formed a wet sloppy "O" with my mouth and let Sam fuck my mouth at his leisure. He soon came pulling his cock out slightly leaving only the head in my mouth and jacked off using my mouth as a dump for his cream which I gladly and with anticipation accepted. I relished and swallowed every drop of my first load of creamy ejaculate.

As Sam finished and softened in my mouth he pulled out and Walt, my first black man inserted his cock in my waiting mouth. He was not longer but was certainly thicker with a large plump head. I was forced to think about the penis invading my rear as the owner growled and lunged himself into me. I could feel the subtle pulsing in my anal ring and feel the man trembling. I knew how a woman felt knowing she had done her job and brought pleasure and relief to her man. It was an exquisite feeling. I felt the dick sliding out but waited only moments as another took its place.

I felt something being tied around my ankles. My legs were pulled up with my knees squeezing my breasts and I saw a stretchy ace bandage being tied to the legs of the stool under my head. My hands were tied to the stool legs under my rear. I was completely bound, unable to move away as cocks thrust in and out of my mouth and anal rings.

I thought of Jan, I couldn't see her but knew from the moans and the sound of flesh pounding on flesh that she was getting the same as I was. The sight of me being bound with stocking clad legs splayed must have been too much for the man spearing me as I felt him quiver and jab me with short convulsive thrusts. Very quickly Walt thrust forward slightly. I felt in my lips the pulses as semen rushed up his tube into my waiting mouth. Walt didn't squirt so much, as he flowed like a river. The large spongy head of his cock formed a tight seal not allowing semen to escape my mouth. A lake of creamy semen formed on the roof of my mouth and flooded my nasal cavity. I tried swallowing but couldn't at that angle. The thought passed through my mind of drowning in semen. Walt finally pulled his still hard dick from my mouth allowing me to breath. I swallowed what was in my mouth and once the sensation of drowning in semen had passed, thinking of the amount of sperm in my belly and now swimming in my sinuses was highly erotic.

I had another cock slide in my rear quiet easily. My ass was becoming pliable with the constant use. I heard Jan say she'd had enough. I lifted my head to see Jack; Robin's other black friend above me. I enjoyed watching on his face the pleasure he was receiving as I loosened and tightened my anal rings, milking his shaft. Finally I looked down, over my massive cleavage between my legs to see his beautiful shaft as he impaled me with every thrust. The veins were very prominent and a white frothy sheen was evident on the body of his cock. Then it hit me, white frothy sheen and no condom. Jack had not been here to hear the rules and whoever had fucked me last had fucked me bareback as well to produce the froth. Before I could say a word Jack fell into me and groaned with his head in my cleavage and in my neck. I felt his penis throb. Knowing I could do nothing at this point I tightened my grip on his shaft so I could feel every pulse. I knew at that moment I was being bred with my second load of sperm. Scary but powerfully erotic.

Once Jack uncoupled himself from me my bounds were released. Thinking it was over I stood and stretched. Then I bent over to touch my toes. Wrong thing to do dressed as I was amongst a group of horny men. Ron one of the brothers came up behind me and shoved his cock in me in one thrust. It slid in so quickly with all the slimy cum lubricating it I was full of his meat before I could think. He pulled me to the other bed backwards and I fell on him jamming his pole in me hard. He pulled up my legs which his brother Larry crawled between. Larry then roughly shoved his cock into me next to his brother's cock. They plowed me, both pulling out and ramming back in at the same time.

The other men crowded around encouraging them to"fuck her hard" and "fuck her deep". It was so easy to hear this and think of myself as a female and my ass as a pussy. The relentless rubbing on my prostate caused me to ejaculate, a slow deep throbbing contraction from deep inside. My orgasmic contractions caused them to cum as well, drenching my insides.

Once Larry dismounted I rolled to the side of Ron. I was in a blissful state, tired and content. I felt myself being pulled and rolled. I looked up from the bed. My legs were bent and open and the guys surrounded me. Someone began using fingers in the sloppiness of my hole. Instinctively I pulled up my knees. Someone on each side helped me lift my legs higher. I felt the pressure increase. I heard somebody say "one more" then "a little more". I was being stretched beyond any where I'd been before.

Finally I felt a pop along with some relief and I knew a hand was inside me. It was incredible. My eyes were closed as I concentrated on adjusting to the pressure. I opened my eyes as Mike crawled over me and slid his cock in with the fist and fucked me. I couldn't move or speak. I was simply a toy doll for everyone to fill. My legs were hoisted over shoulders or hooked around elbows till everyone had ridden the new ride. Finally the fist began a waving motion in me massaging my insides with slimy cream. I wondered how many sperm were swimming in me. Jan wrapped her lips around my cock and I exploded in the most intense orgasm of my life.

I don't remember anything after that. The next morning I awoke with Jack wrapped around me and Jan and Mike in the other bed. I was still dressed from the night before. When everyone awoke we had some serious discussions about the breach of rules. They told me everyone had agreed to be tested after I passed out. It turns out all were clean and we became a regular group including Robin.

Jan and I did take care of the morning wood that day as well.

I hope you enjoyed this story. You may disagree with it but it is what it is and I am what I am. It's fairly close to the facts except for the names.

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bycdandie© 8 comments/ 136315 views/ 36 favorites

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