Dream Date

This is one of my first stories and the very first one on this subject. I hope it is not too long and boring. As with most of the things are write, it is a work of fantasy - other than the second paragraph J. Let me know if you think I did okay. Here goes nothing:

I had been anxiously waiting for this night for a week now and as I got ready I felt like a teenager getting ready for a first date. For God’s sake, I’m 45 years old I thought. I feel like I’m going to forget my own name. But it was a first date in many ways. It was my first date in over 25 years – since I met his wife. And my first date with a transsexual! So it was a mixture of anticipation, anxiety, and guilt that filled my brain.

I had come across Dani on the internet. I’d become enamored with her the second I had seen her pictures. I always had a strong curiosity but she had struck a chord like no other. We had exchanged a few emails regarding the pictures she posted. She was polite but I figured I was just some schmuck to her.

But when I found out I was traveling to her area on business I thought I’d take a chance and see if she would be interested in doing dinner or something. It took me a week and several emails to build up the nerve to ask. She asked for a day to think about it and responded with a yes with the ground rules that it was for dinner only and I was paying. And it had to be someplace nice. We would play anything besides dinner by ear. I quickly agreed and said that being a gentleman I didn’t expect anything different. We agreed upon a meeting day and time for the following week and I told her to pick the place since she knew the town.

Fast forward to now – standing in the mirror, checking my hair for the umpteenth time. Going down my personal grooming list – teeth brushed, arm pits sprayed, face shaved. The meeting at the client had run a little longer than expected so I had felt rushed to get back to the hotel to get ready, but now it seemed like the time was crawling by. The next 10 minutes would seem like hours…

It was finally time to head out. We were meeting in the lobby of my hotel and then taking a cab to the restaurant. I was a couple of minutes early and took a seat on one of the couches where I could watch the door. She walked in right on time and she took my breath away. She was wearing a stunning black dress that showed off her abundant cleavage without being slutty and hugged the rest of her body in all the right places. It stopped about mid thigh but had a slit in the back that ran right up to the bottom of her nice ass. As I crossed the lobby to meet her, I had to try to concentrate on something other than her to keep from springing an erection right then and there. With a polite kiss on the hand we exchanged greetings (to my surprise I DID remember my name) and I asked if we should go right away or if she would you like a drink at the hotel bar. She said we had better be going as she was not sure how long it would take to get to the restaurant with the traffic and we could always get a drink there. So I hailed a cab and off we went on what I hoped would be a night to remember.

Dinner went smashingly well. The restaurant was very nice and we found the conversation very easy. We had several common interests – cars, bowling, guns – that gave us many things to talk about. Guess that is the good thing about going on a date with someone who spent a good part of their life as a guy! The nervousness disappeared and the dinner flew by. As we finished the food and the wine, she reached across the table and grabbed my hand. She thanked me for a great dinner and said “How about that drink back at your hotel now?”

I couldn’t pay the bill fast enough. It took great restraint on my part not to run to the door to hail a taxi. Instead I walked out of the restaurant happy to have this beautiful woman at my side and overjoyed that the dinner had gone so well. I held the door to the cab and admired her gorgeous legs as she slid across the seat. When I climbed in and sat next to her she put her hand on mine, entwining her fingers in mine. She leaned over to me, kissed me on the cheek and thanked me for a lovely dinner. She then put her head on my shoulder and we rode in silence the rest of the way back to the hotel.

As we exited the cab I grabbed her hand to assist her to her feet. I held on to it as we walked into the hotel and to the lobby bar. I was tempted to ask if we could skip the drink and head straight to the room but didn’t want to risk it by going too fast. The bar wasn’t very busy and we picked a somewhat secluded table towards the back. We looked at the wine list on the table and picked out a bottle to share which we ordered from the waitress. We sat next to each other and caught up with the day’s sports on the four letter sports network. As we chatted and drank the wine, she put her hand gently on my thigh, lightly stroking it with the tips of her fingernails. I followed her lead and placed my hand on her thigh which she spread slightly at my touch. I circled his fingertips on her inner thigh, inching up to the bottom of her dress. We both seemed to forget about what was on the TV even though our eyes were pointed towards it. We didn’t even notice the waitress when she first approached to ask if we needed anything else. I removed my hand from her lap asked if we could have a couple of clean glasses to take back to my room with the rest of the bottle of wine.

By the time the waitress came back we were standing, both fidgety and seemingly anxious to get to the room. I knew I was for sure - I was ready to grab her hand and sprint with her through the lobby! I slipped the server a nice tip as I took the glasses from her.

As we stood in the elevator, Dani leaned with her back up against me. Her warmth felt so good to me. And she smelled wonderful as well – a mixture of her perfume and a hint of raw sexuality starting to seep through. As the elevator stopped and the doors opened, we stepped out and took the short walk down the hall to my room.

I set the glasses down on the table and poured some wine into each one. As I turned to give one to Dani, she took it from my hand and placed it back on the table next to mine. She then reached out and put both arms around my neck and lightly kissed me. Our lips barely touched but the shockwave it sent through my body was amazing. It was the most sensual kiss I had ever experienced. As our lips parted we both took a deep breath. She then pulled me back to her lips and this time the kiss was much more raw. Her tongue parted my lips and eased its way into my mouth, exploring my teeth and tongue. I moaned and pulled her tighter, twisting my tongue with hers. I grabbed her firm ass in my hands and pulled her tight to me. My cock was already growing and it did even more as I pressed my body against her. She reached down and untucked my shirt, running her hands up my chest and over my nipples. She pulled her lips from mine and kissed my neck.

She then dropped to her knees and unbuckled my belt, unbuttoned my slacks and pulled down my zipper, letting my pants fall to the floor. She kissed my stomach as she ran her palms over my boxer briefs bringing my cock to its full hardness. She pulled the waistband down and ran her tongue along the sensitive underside of my shaft. She then slid my underwear down my thighs and as she did I stepped out of my shoes and slacks. She slid my briefs off over one foot and I kicked them across the room with the other. She wrapped one had around my hardness and stroked me as she kissed her way back up my leg. As her lips reached my groin, she continued her kisses up my shaft and when she reached the head her lips parted and she took my cock into her warm wet mouth. She ran her tongue around the tip at which time I uttered “Oh yes baby” and ran my fingers through her hair. She seemed encouraged by this and started taking my average sized cock further into her mouth. After only a couple bobs of her head, she took the entire length of my shaft into her throat. She paused with the nose buried in my neatly trimmed pubic hair and her chin resting against my balls. She moved her tongue on the underside and damn it felt good. She then started working me with her mouth, deep throating me every third or fourth trip down while also working my shaft and balls with her hands. It was feeling spectacular. I was contemplating whether or not I wanted to cum this way or have her stop she when took a finger and ran it down my ass crack pressing firmly against my puckered asshole. As she pressed it past the entrance it was as if she was pulling me to her and burying my cock in her throat. This took any decision about cumming out of my hands. As her lips reached the base of my shaft and her finger slid in past the second knuckle and she pressed against my prostate I exploded into her mouth. My legs shook as she pumped her finger in my ass a few times and I held her head to my crotch – almost as much to steady myself as to keep my cock inside her soft mouth. After taking a few squirts down her throat she pulled her mouth off of me and pulled her finger out of my ass causing me to spasm as it slid past the outer ring. She continued to take my cum into her open mouth as I pumped out more streams of cum. Once I finished she stood and kissed me passionately. The remaining residue of my cum mixed with her own saliva tasted wonderful. I kissed her back with the same energy and couldn’t wait to taste her cum.

I pulled my lips from hers and gently kissed her neck. She tilted her head back and opened it up for me to cover it with soft wet kisses as I cupped my hand around the back of her neck and lightly stroked her skin at the hairline. As I did that, I reached around and undid the zipper on her dress with my other hand. I slid my hand from the back of her neck across her shoulder sliding her dress down her arm. As I traced a path of kisses along the top of that shoulder I slid the other strap of her dress down. She slid her arms out of the dress, letting it fall to rest on her hips, exposing her lovely red trimmed black bra which held her very large breasts. I lowered the straps of her bra in the same manner I did those of her dress as I kissed lower on her neck and over her collar bones.

As I kissed down into her ample cleavage, I slid the bra cup off her right breast, exposing her pierced nipple. Taking it in my mouth, I played with the ring and the nipple before enclosing both in my mouth and sucking quite hard. She moaned and pulled my head tight to her breast. She was obviously enjoying this. My right hand found her other breast and I freed it from its bra cup, first pulled firmly that nipple’s ring, then cupped her breast in my hand and massaged it. I alternated these two actions on her left breast while suckling hard on her right. I was in heaven and she seemed to be enjoying it very much as well.

I moved my lips to her other nipple and ran my hands down the sides of her body until they reached her dress. She assisted me in pulling it down over her hips and ass and as it fell to her ankles I cupped her beautifully firm ass. Meanwhile she reached behind her and under the clasp of her bra and tossed it onto the chair.

With my hands firmly squeezing her ass checks, I pulled her close to me while moving my lips from her nipple to her lips and we kissed passionately once again. After a half a minute or so of this, I turned my body slightly and ran the fingertips of one hand along the top of her matching black panties around to her flat stomach and took the plunge under the lacy waistband and found her cock waiting for me. I was happy to find that it was not fully hard because I wanted to feel it grow.

With my hand on her cock, I guided her to the bed and had her lay down. I climbed up and knelt alongside her. I kissed her full lips again and my fingers played with her nipple rings. My hand moved to caress her smooth belly while my mouth replaced my fingers on her nipples. As my hand moved down to her panties, I rubbed her cock through the silky material. I moved down the bed until I was kneeling beside her waist. At that point I hooked my fingers in each side of her waistband of her panties and she lifted her hips slightly to help me slide them down her legs, releasing her marvelous cock. It was at half mast as she used her feet to finish removing her panties. As she did, I maneuvered myself between her legs. I took her cock in hand, stroking it as I stared at it in wonder. I felt so good in my hand – still fairly soft but getting harder. I leaned in and took it in my mouth, just the tip at first, swirling my tongue around the tip. I would never have dreamed of sucking a man’s dick, but with this beautiful tranny with her knockout body it felt so natural. I took more of it in my mouth, lowering my face over it, taking advantage of it not being fully erect to take almost all of it before triggering my gag reflex. As I slid her in and out of my mouth, I could feel her growing, filling me more and more. The feeling of her cock swelling in my mouth was wonderful. I was able to take less of it on each stroke, but between my saliva and her precum I thought I was doing an OK job for a rookie. I was stroking her shaft with one hand in rhythm with my sucking and playing with her balls with the other – cupping them and rolling them between my palm and her body. As I did that I used my fingers to press against her between her ball sack and her asshole.

I let her now fully hard cock slip from my mouth and ran my tongue down its shaft to her balls which were completely shaved (like most of her pubic hair, save for a small patch up top). I licked them with the flat part of my tongue and then took one of them into my mouth. I ran my fingers over the puckered outside of her asshole, pressing against it. I placed my hands under her thighs lifting her legs slightly. She went even further and lifted her knees towards her chest and rolled her ass into the air. I moved my hands, grabbing a handful of ass cheek with each one as I let her scrotum pop out of my mouth. I ran my tongue down it to the sensitive flesh right below and then to her asshole. I kissed it and started pushing my tongue into it. I love eating out ass and hers seemed to taste extra sweet. I alternated between probing inside it with my tongue and licking her from her crack to her balls and everywhere in between. As I executed my oral attack on her ass, she stroked her cock. It was one of the sexiest things I’ve ever been a part of. She then reached down and put her hand under my chin, pulling me up to her face. She breathlessly said “I need you to fuck me” and kissed me deep and hard.

She asked me to go grab her bag for her. I handed it to her and she reached in for condom and some lube. I knelt between her legs and she expertly put the condom on for me followed by a generous dollop of lube. She also put some on her fingers and rubbed it on her asshole, sliding a couple of fingers into her own hole. Once she felt she was properly lubricated, she took hold of my cock and pulled it to the entrance of her ass. I moved my hips forward with a firm, slow push, pushing past the initial muscle and into the soft warm passage of her ass. I continued until I was buried completely inside of her. I paused for a bit to enjoy the feeling and to look down at her beauty as she lay below me. I slowly pulled back on my cock, taking it almost all the way out before sliding it slowly back in. I built up the pace gradually, not because I didn’t think she could take it, but because it just felt so good. She had her hands behind her knees, pulling them to her body, opening herself up to me fully. As the pace quickened I loved the way her tits and cock bounced to the rhythm. Damn this felt so good and from her moans and labored breathing I could tell she was enjoying it too.

After a few minutes I was about ready to cum. I pulled my cock out of her and pulled off the rubber. With a few strokes of my hand I started to cum, arching my back and sending a load of cum that left a trail from her cock to the middle of her stomach. Several more spurts left her cock and balls with a good coating of my milky white cum.

Once my body stopped spasming, I leaned down and started licking her clean. Some cum was dripping down her balls and over her asshole so I hungrily ate it up. I continued lapping up my cum from her cock and up to her belly, making sure to still have some in my mouth as I reached her lips. As we kissed I slid my cum covered tongue into her mouth, sharing it with her. Tasting my cum from inside her mouth was even better than from her body.

She then moved her mouth to my ear where she nibbled on my earlobe and then whispered to me “Would you like to be fucked”. In my extremely aroused state I could hardly get out a “Yes please” but I don’t think I left any doubt in her mind that I was ready. She kissed me again and told me to get on my hands and knees on the bed. With my ass in the air, she moved behind me and now it was her turn to eat my ass. Her tongue felt wonderful as the expertly ate me out. She reached under me to play with my balls and my cock which was now starting to come back to life.

She picked the lube back up, applying a liberal dose to her fingers and rubbed it on my ass. She slid first one finger and then two into my ass. I was well lubed so they slid in fairly easily and she started to finger fuck me. Much to my disappointment she removed them and reached back into her bag for a second condom. She placed this one on her cock and put a coating of lube over herself. Seeing her stroke her shaft to get it slick all over was such a turn on. Knowing that she was about to stick that very large cock in my ass was a turn on but a little scary as well. I’ve had fingers, anal beads, and small dildos in my ass before, but never anything this big. And while it was a little frightening, I somehow had all the trust in the world in her to make this nothing but the pleasurable experience it should be.

She positioned herself directly behind me and placed the tip of her cock on my rosy red asshole. She put just a little bit of pressure on it and told me to relax. With that she started pressing forward. Damn, it was a little painful but it felt so good as it started to open me up. I found myself pushing back against her as she pressed it past the tight outer muscle. Shit (maybe the wrong use of words), this hurt but still I wanted more. I wanted her inside me. The pain reached its apex as the head of her cock popped fully into me. Both of us stopped pushing at that point and relaxed as my ass got used to her girth inside of me. After a short pause, I started pushing back against her again. I had to feel more of it in me. This time she stayed still and let me control the penetration. I took about an inch at a time with short pauses in between. Soon I had all 8 inches buried in my ass. At that point she said “Great job lover, your ass is so tight.” I slowly started pulling away letting her cock slide back until the head was pulling against my sphincter before pushing it all the way back in. And I did that again. I cannot begin to describe the feeling as I repeated the motion. As I picked up the pace she started moving her hips in rhythm with mine - her groin meeting my ass at full stroke. Soon we were fucking like there was no tomorrow. Her hands were on my hips pulling me into her with each thrust of her cock. I had reached up under myself and was playing with my own cock and pulling on my balls. The pain caused by my ass being stretched to the hilt had dialed back to a dull throb and actually added to the pleasure I was feeling by increasing the overall sensations I was feeling.

Suddenly she pulled out of me, slapping my ass before sort of shoving it away and telling me to turn around. As I did she peeled of the condom and stroked her cock with one hand. Still on my knees and facing her, she reached out and placed her other hand on the back of my head, pulling my face towards her hardness. I didn’t need any more of an invitation. I took her cock into my mouth for the 2 nd time of the night. I sucked hard on it, eagerly taking as much of it as I could. And this time I think between the lubrication from her precum and my high level of sexual excitement it seemed like I could get it much further down my throat this time. I definitely wouldn’t consider it deep-throating but it was closer at least. As I sucked her off, I put a finger up her still lubed ass and pressed on her prostate. Much like it had done to me previously it put her over the edge. She started to pump loads of cum into my mouth. I’ve always loved to make women cum orally and this was no different. Her body was twitching and spasming as she continued to cum. The feeling of her cock pulsing in my mouth was unbelievable.

As she came back down to earth, I made sure to save the last few spurts of cum in my mouth so as I left her softening cock slip from my mouth and rose up to kiss her, I could share her cum with her much like she had with me. We kissed wildly, exchanging her cum back in forth in our mouths. As we did she, reached down and started stroking my still hard cock. She pulled away from my lips and traced her tongue down my chest and stomach to the tip of my cock. She asked me “Are you going to cum for me again baby?” I reached down and started stroking myself as she ran her tongue around the head of my cock. It didn’t take me long to reach the boiling point. As I moaned “I’m cumming” she opened her mouth and took what little cum had left the 3 rd time around onto her tongue. When I was done and she had licked every last drop off my penis, she looked up at me with her mouth open and a pool of cum on her tongue and swallowed it down. She smiled, licked her lips, and rose up on her knees to kiss me. After a quick kiss, I pulled her down onto the bed with me. With her laying snuggled up alongside me with her upper body of luscious breasts on my chest, I held her tight and whispered in her ear “Will you stay the night?”