This transgender story contains adult themes dealing with crossdressing. If you are too young to read such a story, you are offended by such themes, or it's illegal to read this where you live, then stop and don't read any further. _________________________________________________________________
Convention Center 3
Sunday morning good old Mr. Sunshine rousted me out of bed earlier than I would have liked, especially after last night. After my morning discussion with Mother Nature, I went back to bed. Stephanie was still asleep but not for long. I started pinching and sucking on her nipples. She smacked me on the top of my head and scolded me with "Stop that". I looked her in the eye, smiled, and said "Thank you for last night. It was incredible".
"Do you always sleep dressed like that" referring to my not so new lingerie. I was still dressed in my teal and pink bra & panties and stockings.
"Watch it. This was a gift from my lover" I acted hurt and turned my back to her. She snapped my bra strap as she headed for the bathroom. I followed her smacking her on the ass. After she peed, we undressed each other and got in the shower. I could not take my eyes or hands off of her breasts. They were perfect. Not to big, not to small, with large pink areolas. These are the kind of breasts I would want if mine were real I thought to myself. Before we finished showering, she bent over and wiggled her cute ass at me. I got the hint and she got impaled.
Debbie popped into the bathroom as we were drying off holding a bag of goodies. "Did I miss anything, Ladies?" Neither of us admitted to anything but we both wore guilty grins. She opened her sack and handed Stephanie some clean clothes. "Sit down and close your eyes" was all she said to me. I lowered the toilet seat cover and sat down. The girls giggled as they put a wig on me. "Open". What I saw shocked me. It was an older "Pageboy" style light brown wig. It looked great on me.
"Except for the facial hair, she's a natural" exclaimed Stephanie. Diane reached into her bag, produced an electric hair trimmer and removed my facial hair. "You can do the rest before we leave".
"Leave" I asked?
"We're going shopping you silly girl" Debbie responded. Now finish up and get dressed. As I finished shaving and stepped out of the bathroom, the girls were inventorying the contents of my "special" suitcase. They had picked out my denim skorts, a tank top with a built in shelf bra, my B cup forms and my denim shirt/cover up. Also laid out was my merry widow & petticoat which I had worn for Stephanie on Friday night. Debbie held it up against herself and said "I'll bet you were a knockout in this. Can I borrow it tonight?"
"Tonight, what's going on tonight?" I asked.
"You'll see, that's why we are going shopping, silly" Debbie responded. I looked at Stephanie. She shrugged her shoulders and said "News to me girlfriend". After dressing in the outfit they picked out with the wig and some makeup, damn if I didn't look like a real woman. Debbie handed me a purse to carry my stuff in and said "Let's go".
I stopped them. "The convention, I'm supposed to be there right now". Debbie looked at me and smiled "You look pretty good for someone with mild food poisoning." "I posted a sign at your booth an hour ago. If there's nothing else, let's go".
Minutes later, we three gals headed out for some shopping fun. I have never in my life had so much fun shopping. Debbie was on a mission and Stephanie & I were passengers. All we were told is we are going to a private party. I got my first ever real manicure and spa pedicure. I received instruction on how to best apply my makeup. I think the gal who did my makeup knew I was a guy, but never said anything. Debbie found the perfect dress for me to wear to the party. The dress was way too cute. It was a black micro fiber stretchy "off one shoulder" and it had this "poofy" ring of chiffon and lace around the hips which was perfect just in case. The balance of the afternoon flew bye.
Back at the room, Debbie grabbed my merry widow outfit and left Stephanie and I to get dressed.
When Debbie returned, WOW did she look good in my outfit. The only added items were a short Bolero style lace jacket and 5" thigh boots.
I wore my new dress, the bra & panties I wore to dinner that started all of this, my lace top stockings and my new slutty 4" ankle boots. It felt amazing.
Stephanie was in a similar strapless black dress, crotchless black tights and a pair of 5" open toed pumps. Because she was braless, she bounced with every step she took. I was jealous.
We grabbed our stuff and headed out. In front of the hotel, Debbie waved at a guy sitting in a car. The guy started the car and drove over to us.
"Good evening ladies, (taking my hand, he said) my name is Jeff. You 3 ladies look absolutely incredible tonight. Please get in". Once inside, he closed the doors and off we went. I whispered to Stephanie, "Who is this Jeff guy". To which Debbie responded "Your Date".
"My date" I softly inquired through clenched teeth. I stared at Debbie with the same panic look in my eyes as I did last night when Stephanie invited Debbie to our private party. She squeezed my hand and smiled. "It's OK. It will be a night to remember, trust me?" We arrived a few minutes later at one of the "Alternative lifestyle" clubs nearby.
Jeff was the perfect gentleman. He opened the doors for us and escorted us to an available table. When he left the table to order our drinks, I glared at Debbie.
"Look, everyone here knows that Stephanie & I are together. However, to some of the locals, you are nothing more than fresh meat. Welcome to our world. Jeff is here for your protection more than anything else. OK." Debbie continued "If you don't want to do anything, then don't do it. Jeff only knows that this is your first time out in public as a woman. If you do decide to explore our world, Jeff is magnificent in bed."
When Jeff returned with our drinks, he served me first then Stephanie and Debbie. He moved his chair to sit next to me. We talked about music, hobbies and other things, nothing to serious (for a first date). Debbie interrupted us with a hand motion that we should go dance. He took the hint and escorted me to the dance floor.
The first song was ok; I was not impressed with it. The second song was a slow song. Wow, the feelings I got when he wrapped me in his arms were amazing. He held me tight. I could feel his body heat. While we danced, I felt a strange sense of calm or peace that I've never felt before. As the music ended, I kissed him. Not just any kiss; I placed both of my hands; one on each side of his face, looked him in the eyes and tongue kissed him. When we separated, I don't know who was more embarrassed he or I. I held my head down. He guided my chin upward with his finger and smiled at me. As we walked back to our table, one of the locals tried to steal me for another dance; Jeff removed his hand and said the lady is with me tonight. Our companions witnessed everything.
At the table, Debbie instructed us to finish our drinks as they were hungry and wanted to go and eat dinner. We left there and went to "Kelly's Steak House".
Both Debbie and Stephanie knew the hostess so we were ushered right in to a private booth in the back. Jeff excused himself and left us girls to gossip.
"OMG" said Stephanie "that was some kiss you laid on him on the dance floor".
"I don't know what came over me. I was one of the most incredible kisses I've ever had. It was one of those; time standing still moments" I said. "Debbie thanks for inviting Jeff this evening. If I seemed ungrateful earlier, I apologize."
Jeff returned in short order with another round of drinks. Merlot wine for me, umbrella drinks for the other two ladies and a gin & tonic for himself. He was followed by our server with two sampler trays of appetizers and menus.
"Do you like prime rib" inquired Jeff. I nodded as I had a mouth full of food. Looking at our server he said "We will have the prime rib for two, please". After the other two ordered, Jeff raised his glass and toasted "To a wonderful evening". We all shared in his toast and took a drink.
When I excused myself to go to the ladies room, Jeff stood. The three of us disappeared into the ladies room. I attended to my business and touched up my lipstick, it was still messy from our kiss. Stephanie & Debbie were going nuts with the questions. I was lost to answer some of them as I didn't know what I was feeling or where this night would end up. As we were leaving, I heard Steph bet Debbie that I would go all the way with Jeff tonight.
Dinner was superb. We passed on desert as we sat and finished another round of drinks. It was decision time for me and being tipsy did not help. Was I going home alone or with Jeff? If Jeff went with me, than I would be his woman for the duration of the evening. I looked at both Stephanie and Debbie and smiled. They knew my decision without me speaking.
Debbie took the lead and said "Jeff can you please take Stephanie & me home, both of us have to be at work early tomorrow".
Jeff turned to me and asked if I was ready to go. I emptied my glass and picked up my purse. It was a short drive to the girl's apartment. I waited in the car as Jeff walked them to their door and gave each of them a hug and a kiss on the cheek good night. Debbie spoke to him for a minute before going inside herself.
Jeff sat silently at the wheel waiting for my response to his question. Did I want him to take me home or go and get some coffee because he was having such a great time and was not ready for this night to end?
"Please take me back to my hotel and like you, I'm not ready for this night to end either. I can make us some coffee in my room." I smiled and then placed my hand in his lap. He smiled too.
At the hotel, we walked to my room holding hands. I handed him my key. He opened the door, turned on the lights and ushered me inside. Before I could ask him about the coffee, he returned the kiss from the club. He took my face in his hands, stared into my eyes and kissed me. I melted into him. I placed my hands on his crotch and gently squeezed. I was now holding another mans penis as it grew. There was no turning back now. I wanted to be his woman tonight.
I undid his belt and slacks. They fell to his ankles. I was now holding his erection in both hands and loving it. He pushed me away, looked me in the eyes and said "Diane, are you absolutely sure you want to do this? I will not force you to do anything you are unsure of or unwilling to do".
"I want to be a woman, your woman tonight. I want to satisfy you the same way any other woman would." As I spoke, I continued to squeeze his (now my) cock. I pulled down his briefs, sat him on the bed and finished undressing him from the waist down. As I knelt before him with his cock in my hands, I felt no apprehension. He was large but not huge. I started licking the underside of the head, playing with my new toy. I had sucked my dildo to its base before, so Jeff was in for a treat (I hoped). I played with his balls while I sucked on his pole. The harder he got the less of him I could get in my mouth. So I wrapped my right hand around its base and concentrated on keeping his mushroom in my mouth. After a few minutes, he started breathing faster. I pulled on his sack and fingered his G spot with my left hand and started pumping him faster with the right. When he grabbed my head, I let go of his cock and relaxed my throat as much as I could. He was now in charge. He was fucking my face. I continued to pull his sack and squeeze his balls but now that my right hand was free I started to finger his ass. His grip on my head tightened while his cock expanded. He was getting close. I increased the finger pressure on his G spot and his anal ring. He started shaking then pulled back to where just the head was in my mouth and erupted. I swallowed and swallowed and swallowed some more. As he softened, I was able to deep throat him and sucked even more out. He had to push me away to get his cock out of my mouth.
"I did not want to cum in your mouth but that was incredible" Jeff mumbled.
I smiled at his complement. I had the feeling that Jeff was straight and yet he knew from the beginning that I was different. He never once treated me like anything but a lady. I continued to play with his balls and run my pink nails up and down his legs. He was starting to get his second wind. I was ecstatic. I was still fully dressed in what I had worn for the evening. It was such a wonderful dress I never wanted to take it off.
"Would you like to slip into something a little more comfortable" asked Jeff.
"I would, except Debbie borrowed it to wear to the club tonight". I could not help it, I started to laugh. He started to laugh with me. Before I knew it, I was telling him the entire story from the note in restaurant Friday night about my bra strap from Stephanie, meeting Debbie on Saturday when she hand delivered the pink & teal lingerie to the convention center, today's shopping adventure and how incredible it was. The entire time I babbled on and on like a teenage girl about the last 3 days, he just sat and listened and watched a private fashion show. I was the only thing in his universe at that moment in time and he was not going to miss a second of it. I paused when he placed his finger to his lips.
"You are one of the most incredible ladies I have ever met. Now I know why Debbie and Stephanie spoke so highly of you. It has been my privilege to spend tonight with you." He motioned with his finger for me to approach him. I obeyed. He started to undress me. It was all I could do to just stand there, this was uncharted territory. When he could not find the zipper to my dress, I lifted my arm. The zipper opened and he removed my dress. I don't know why I stopped him from removing my bra, panties and stockings but he seemed to understand and he respected my wishes. He laid me on the bed on my back dressed only in my lingerie. He picked up his trousers from the floor and produced a condom. Holding the condom between his fingers he spoke. "Would you like the honor or shall I".
I smiled and said "No thank you, please put that away". He smiled too and returned the condom to his pants pocket. What happened next still amazes me. He pulled my "clit" out a leg opening and started masturbating me. I came almost immediately. He then rubbed my juices on my "pussy" and his now very erect cock. Placing my legs over his shoulders, he started penetrating my pussy. He moved very slow, watching my face the entire time for any indication of pain. After several minutes, his cock (my cock) was completely buried in my pussy. Then he started to fuck me slow at first gradually picking speed. I heard myself moaning and using my legs to impale myself deeper onto his cock. He held my hips tighter and picked up speed. Soon he was slamming his cock into my pussy. At one point, I heard myself scream "Please fuck me forever". He continued to dominate me by fucking me harder and faster. Then I felt it. I felt his cock getting larger and stiffer. Payday was moments away. His grip on my hips tightened more as he pulled me onto his cock one last time and held me there. It was amazing to watch his face at the same time feel him pumping more cum into my pussy. He held tight for quite a while; he even slapped me on my ass because I was trying to fuck myself on his magnificent tool. My panties were soiled because I had cum from the incredible stimulation and pleasure Jeff had given me.
When he pulled his cock out of my pussy, we heard the pop. He excused himself and went to clean up. I was standing up waiting for him to return. As he re- entered the room, I wrapped my arms around his neck and kissed him. "I now feel like a woman thanks to you. I kissed him again as I helped him get dressed.
"Thank you Madame for an incredible evening tonight" was the last thing he said as he departed.