Shemale Does Dating
I suppose that technically, I had already had my first real date when I went out with Steve back home but I really did not consider it to be since I had already fucked and been fucked by my athletic friend and it was more a show than anything else.
School had settled down and over the couple of months following that horrible first day, I managed to keep my head down and out of trouble. I had passed the registrar in the halls on a few occasions and, although nothing was said subsequent to them saying that I could not attend university as a shemale, he always addressed me with a side-ways grimace and the name Colleen always seemed to stick in his throat. On one particular day as I was coming out of my advanced physics class, he stopped me in the hall and asked me to come to his office. The first thing I thought was that the son of a bitch was about to blow me out of school. I followed him to his office trying to think of my response and how I would deal with him and inside, I sat across from him.
“Colleen,” he began, “you know I am not big on you being here as a shemale but I have been following your progress and I am impressed by your intellect as are all of your professors. We have a guest professor coming from the west coast late next week who is lecturing in another discipline but he has asked us to fix him up with someone to take to the Met for a Pavarotti performance. He is gay but has not come out of the closet because it would kill his perceived integrity so he asked if there were any shemales that were not boys trying to look like girls. It did not take us long to think of you and since you look nothing like a boy trying to be a girl, we told him we thought we had just the right young lady for him.”
“Gee thanks,” I said unsure about how to address the slight-handed comment. Since I too loved the opera and was a big fan of Pavarotti, I told him I would be delighted to accompany the visiting prof but was not guaranteeing any additional benefits after the opera. He assured me that there was no pressure for any extracurricular activities and his primary focus his to have a woman on his arm for the opera. I agreed and the registrar said that my opera date would pick me up at 7 on the following Friday evening.
When I got home after school, I told Linda my exciting news and then gasped. “I have nothing to wear to the Met,” I declared. “What am I going to do sis?”
Linda smiled that knowing smile and replied, “I think me and my girlfriend need to go shopping.” And did we ever shop. It took us all day on Saturday but finally found this sweet black gown that fit perfectly and, of course, the purse and high heel pumps to go with it. I had played with high heels before but this would be the first time I had worn them outside, so I practiced every chance I got. By the next Friday I was ready.
Linda and I started right after school getting me ready. She helped me make sure that there were no stray strands of hair around my cock and I shaved my underarms. This time, I really took my time putting on my makeup and once I was dressed my sister simply said, “Wow Colleen, you look awesome.”
The limo driver called up and I went down to the lobby where my gentleman date was waiting for me. Like David, he did not look or sound gay but he was clearly more dignified than my friend back home. “I am so glad you agreed to do this for me,” he said calmly. “Do I look alright?” I asked as my confidence wavered ever so slightly. “You look amazing Colleen. I know who you really are and I would never think that you were anything other than a beautiful woman.” I could feel the blush rising in my cheeks beneth my makeup as he extended his arm for me to slip my hand into. Professor Wainthrop was a consummate gentleman. He held the limo door open for me and helped me inside and then slipped through the wide opening to sit beside me. We immediately got along well. As impressed by his intelligence as I was he assured me that he was equally impressed with mine but what I did not say was that although he was twenty years older than I was, this man was really really hot. He obviously worked out a lot and his grooming was impeccable. As we pulled up at the main entrance to the Metropolitan Opera House, I was beginning to think very seriously about whether he manscaped right down to his cock.
The opera was incredible and to hear my idol in person literally brought tears to my eyes which seemed to inflame my date’s desires more as he softly stroked my thigh causing me a bi of discomfort. It was not as though I did not want the attention, but he was really beginning to turn me on which, when your cock is tucked securely under your bum, it can be a bit stressful. After the show was over and the dim lights were turned up, he asked if I would like to have some dinner at one of the finest restaurants in Manhattan. I quickly said yes. After dinner, he grew silent and, as we sat in the back of the limo I asked if I had done something to offend him. It was his turn to blush and he said no but he was trying to muster the courage to maybe ask me back to his hotel room for a night cap. Now you have to realize that I had been the proper young lady all night - well as proper as any shemale can be - and it startled him when I leaned over, kissed his cheek softly and replied, “I would be really disappointed if you did not. I have to be honest, “I whispered seductively, “I can’t wait to get out of this dress.” The tension relieved he said, “I can’t wait to get you out of it!”
Inside his hotel suite, he took off his tuxedo jacket and poured us a drink. “You look uncomfortable,” Ron said to me. I smiled in response but playfully said, “A young lady cannot get undressed before the man. It would not be proper!” He was on his feet in a heartbeat and stripped down to his boxer shorts. I was right about Ron Wainthrop working out. His belly was rippled like a six pack and his chest was so strong and muscular. I needed to hold him and beckoned him to come to me and then reached into his fitted boxers and wrapped my fingers around his swelling dick as I placed a delicate kiss on that sweet belly. I removed my hand and stood up asking him to unzip the long zipper on the back of my gown and he did. His hands felt so good as he slid them between my dress and my own flat tummy and then moved up to encase my bra covered titties. I was in heaven. I was being treated like a woman by a guy who wanted all of me. I took off my dress and stood before him in my thong and my matching satin bra and my high heeled pumps that only served to so exquisitely define my legs and I could see that Ron loved what he saw. Then, I climbed onto his bed where he joined me after he slipped his boxers off and showed me his very neatly groomed cock. Boy was he good at manscaping and better yet, he knew that he was about to put that hard cock into a very horny shemale. He was a lot bigger than Steve was an his cock kept pulsating from his excitement which really turned me on. I could not wait. I reached out and took that hot thick flesh in my hand and immediately began stroking it while he rubbed my tits through the bra that I was still wearing. My own dick was beginning to strain to get free of my thong and as I began to lick his sweet stick, I began wiggling my way out of my confines until I was finally free. Ron and I slumped onto the bed where we shared the fun of sucking on each others hard cock until I could not stand it any more. “I want you to fuck me so bad right now sweetie,” I purred when I took my mouth off his cock. “Me too,” his voice raspy from desire replied as he moved around while I lifted my feet over my head. Ron was a great lover! He started off by licking my perky little ass until it was nice and wet as his hands kept fondling my balls. Of course, I was playing with my tits all the time. Then, I closed my eyes tight as he began kissing his way up my tummy and then sucking on my titties. I could feel the swollen head of his cock now pressing against my ass and I wanted him. I reached down and grabbed his hips, pulling him forward until he started to spread my hole. I was so excited that he pretty much slipped right into me. The sensation of my own cock trapped between our bodies as he fucked me hard was way too much for this beautiful shemale and before long, he was loading my ass with his man cream and I was squirting mine between our bodies perhaps sticking us together for all time. That night, we had sex three more times together and then we showered and went to bed for the night as he held me close to his warm bodies. I knew then that being a shemale was the only way I would or could be. Before Ron left for home, he asked if he could see me again and I told him I would always be there for him when he came to town. Since he was such a great lover, why would I say anything else. I can still feel that delicious cock caressing my ass.
There will be more about Ron later in these Shemale Diaries so stay tuned. In the meantime, if you would love to meet a hot beautiful shemale like myself (or maybe you will even meet me) why not check out one of the very best Shemale Dating sites around. I am a shemale and I swear by this site. Trust me, the trannies you will find in your area will have you begging for more.
Take care for now and I do hope you will visit again.
All my love
Colleen
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