Never on the First Date

I guess I can be described as a part time Crossdresser and full time Cock loving Sissy. Although I'm still very much in the closet and only very few people are aware of my sexuality. Especially in my professional life.

Last year my company was implementing a new computer program and all Department leaders had to attend a week long training event in a Midwest city. I was looking forward to seeing some old colleagues and putting faces to names of newer colleagues I had only talked with on the phone. In particular Bob Williams who recently took over our South West region. I have talked with him several times and he seemed very knowledgeable and not arrogant at all. He also had a very sexy phine voice.

After checking in Monday afternoon there was a meet and greet in the hotel conference room to go over the week's schedule of events. I caught up with some guys I've known for a while and finally met Bob and found out he was the same age as me, single and absolutely gorgeous. About six foot, brown hair, beautiful brown eyes and very fit. Anyway he had a very nice smile.

We sat together for the meeting and as our CEO wrapped things up Bob asked if I wanted to grab dinner with him and I agreed and jokingly I said "Just so you know I never have sex on the first date" He laughed and said he would keep that in mind.

We got an Uber to a nearby Steak House and as we exited the car Bob noticed there was a Bowling Alley next door and suggested we should bowl a few games after dinner.. I told him that sounded good with me.

It was a good dinner and we were getting to know each other and afterward we walked to the Bowling Alley and soon we were getting along as if we were longtime friends, joking and laughing alot. He kept reminding that we were on a date, throughout the night. And whenever he got up to bowl I couldn't help but stare at his fine ass perfectly encased in his tight jeans.

I don't drink but Bob had about five beers and was feeling no pain by the time we got back to the hotel. We were both in the third floor and as we walked down the hallway he announced this is me at his door and as he was taking out his key card he joked about being a gentleman on our first date and and jokingly said "Since sex is out of the question how about a little kiss?" with that he closed his eyes and pursed his lips. I'm sure ti his total shock I gave him a quick kiss and he almost fell inside his door and his eyes were wide open and I could see the absolute confusion on his face. I just laughed and said "see tou tomorrow handsome " and made my way to my room.

The next day in training we broke for lunch and Bob sat down next to me and learned over to me and in a very hushed voice asked "I know I drank a bit last night but was I drunk or did we kiss good night?"

I said "You asked for a kiss and I thought it was more appropriate than a handshake " and added "It was pretty funny at the time "

"I guess I was asking for it by teasing about the date thing. Pretty funny though I'll give you that." He chuckled.

We were set to wrap up for the day at Three O'clock he asked if I wanted ro hit the hotel gym afterwards and I told him I had to catch up on some Emails and stuff and that I'm not really a Gym type of guy.

About five O'clock I went to the lobby for a snack and drink and ran into Bob getting in the elevator as he was finished with his workout. He was wearing tight spandex shorts a tee shirt and had a towel draped over his shoulder. I could see his bulge was not obscene but very nice. We exited the elevator and stopped and he asked being as we are both hockey fans we can hit the sports bar in the Bowling Alley grab some food and catch the game. As we spoke I thought his bulge was getting a little bit bigger. Or maybe just wishful thinking.

"Are you asking for a second date Bob?"

"Ok very funny " he asked "You in or what?"

We agreed to meet in the lobby at six thirty.

He was really milking the whole date thing all evening staring with opening the Uber door and ordering all the food and so on.

I had made up my mind I was going to do everything I could to get this Stud to fuck me. So When I set up the Uber back to the hotel I added a stop at a 24 hour pharmacy telling Bob I had to pick something up on the way. So when we got to the pharmacy he said he needed something also, luckily the pharmacy chek out was open in the back of the store so I quickly grabbed a four pack of douche and had them double bag it so he wouldn't see it and he got what he needed up front. And was waiting in the car.

We got to the hotel and when we got off the elevator we reached his door and he opened it and turned to me and said "I'd like a good night kiss " and pursed his lips and I leaned in and gave him another quick peck but this time he wrapped his arms around my waist and pulled me tightly to him and planted his lips to mine a kissed me hard as he opened his mouth and forced his tongue in my mouth. After about a minute we separated and all I could say was "Wow" he reached into his pharmacy bag and pulled out a single rose and handed it to me and asked if I would join him in his room and I said I needed 30 minutes to get ready we kissed again and I went to my room and cleaned inside and out in the shower. Put on a pretty pink babydoll and matching satin panties and robe and headed back to Bob's room.

I knocked on his door and when he opened it I know my jaw hit the floor because he was standing there wearing only his tight jeans flashing that sexy smile. I stepped inside and we were immediately making out. I reached down and rubbed his crotch and could feel his cock getting harder so I started fumbling to get his jeans open when he stepped back and said "Here let me help you out baby " as he undid his pants. As he was stepping out of his jeans I dropped my robe and he gasped out loud "Wow baby that's so sexy" when he saw what I was wearing and I definitely took notice that he had called me baby twice now and it felt really nice.

He stood up from pulling his pants off his feet and I saw he was completely naked now and I almost blew my first load just taking in the sight of this ultra masculine beauty. His cock was perfect approximately six inches in length, not to thick, cut and soaked with pre cum. His black pubic hair totally neat and trimmed short.

Almost involuntarily I fell to my knees and started licking all the nectar I could off his cock while trying to insert my whole tongue into his piss slit to get more I had two thirds of his cock in my mouth and I heard him moan lightly and I was so turned on that I wasn't giving this man head I was making love to him through his mangood, so much more than a blow job. After a couple of minutes I could tell he was getting close as he pulled his cock out of my mouth and stood me up and we were back to making out as he was groping my ass hard over my panties. I worked my mouth down to his right nipple and gently toungued and sucked it as it got hard as a diamond and switched and repeated my actions on the left one. He suddenly lifted me by my ass and walked me to the bed and deposited me on my back onto the bed and ran his hands up my legs and commented on how smooth they were. When he reached my panties he pulled the aside and told me how sexy it was that I was completely hairless and my tiny three and a half inch cock was very cute as he took it in his mouth, it felt so good that I only lasted about a minute before I warned him I was going to cum he removed his mouth and said "good baby that's the whole idea" and went back to sucking my cock but this time he inserted two fingers into my pre lubed cunt and I exploaded into his mouth with at least ten ropes of cum that he swallowed as if he was starving for it. When I calmed down he removed his fingers and stuck them sensually into my mouth and I aucked and licked them clean. He put his forearms between my legs as he worked his way up to his knees spreading them out obscenely. I reached down and pulled my panties all the way to the side as he lined his cock up with my hole. And without hesitation he plunged his entire length into me, it hurt a bit but OMG it felt so good. He went crazy and started pounding me with everything he had and he was hitting my prostate with every stroke and within about two minutes we were both cumming, him deep inside me and me all over my belly. When he stopped shaking he lowered my legs and while still inside me he kissed me deeply.

When his cock slipped out of me he rolled onto his back and pulled me over so my head was resting on his chest he was rubbing my hip very gently. I have never felt so safe and satisfied when he asked "Are you ok baby?"

"Oh yeah I am perfectly fine" then I added that I could get used to him calling me baby.

He said "Isn't that what you're supposed to call your boyfriend?"

"I that you're way of asking me to go steady?" I asked.

He said "No that's my way of telling you that you belong to me now and I know we haven't known each other long but I think I am falling in love with you." then said with his sexy voice cracking " Please don't think I'm nuts."

I replied through some actual tears"I don't think you're nuts babe because I feel exactly the same. Now bring that beautiful cock up here so I can lick it clean in the proper way it deserves."