tagTranssexuals & CrossdressersBi-Curious Meets Transgender Escort

Bi-Curious Meets Transgender Escort


It had been approximately a year since my divorce was finally complete. My ex-wife and I had been married for 4 years and didn't have any children, so the divorce was relatively painless compared to other people we knew. We were still friendly toward each other, but just didn't love each other the way we thought we did when we were married.

We separated immediately after we mutually agreed we would divorce and I moved into an apartment. I refrained from dating while we were still married at the advice of my attorney; however I had a strong urge to meet somebody new and move on with my life.

Before I met my wife I had very little experience dating women. She was only the third woman I had been with sexually. When our marriage began to suffer after about 2 years into it I started looking at porn more often. Our sex life was pretty much non-existent because my wife seemed to have no interest. It seemed every time I asked she had an excuse.

It was also around this time that a friend of mine told me about an acquaintance of his who had met a transgender woman and actually dated for a while. It had never occurred to me to even think of transsexuals and sex, but having started looking at porn I stumbled across transgender pages on some porn sites occasionally. At first I ignored looking at transgender women, but after having heard the story from my friend, I took a look and was surprised how attractive some of them were. For many of them, had I passed by them while walking I would never have known and would have found them to be just very attractive women.

Also when I started looking at porn online I realized I had a particular interest in watching women give blowjobs. I found it fascinating that women would gladly let men cum in their mouth or on their face. I realized this was porn and not necessarily reality, but I had one girlfriend in the past that seemed to like it as well. That wasn't the case with my ex-wife however since she rarely took me in her mouth and she never let me cum in her mouth.

As I watched more porn I realized I wasn't disgusted by the men's cocks and was actually rather interested in what it would be like to give a blowjob. I wasn't attracted to men at all, but I was very attracted to some of the transgender women and their penis enhanced that attraction. I began to fantasize about being with a transgender woman when I masturbated.

So finally after my divorce papers were signed I decided to look into what the possibilities were. A lack of interest in men in general made going to a gay bar not very appealing and I didn't know if any transgender bars existed. So I decided to look online to see what options existed. In doing so I came across several websites that featured transsexual women offering escort services. I knew this was likely unsafe, but after reading many of the profiles I came to know that many of them expressed on their pages how serious they were about being disease-free and ensuring their partners were protected.

There was one in particular that really interested me. Her name was Sonia. She was gorgeous, and reading her reviews online turned me on. From the reviews and pictures it was evident that Sonia was quite well endowed and was able to cum, including some accounts of multiple times during a session. She was also willing to meet newbies like me and she claimed she was happy to take charge and play the dominant role.

I jerked off to Sonia's reviews many times and each time I asked myself whether I would have the courage to actually suck somebody off. If I was to attempt meeting somebody like Sonia I would have to know beforehand. So I experimented with tasting myself.

Initially I tasted my precum as I jerked off. After a few times I began to like the taste but I knew sucking off a cock would be a much different experience. I eventually got the courage to try and lick some of my cum after I came on my chest. I took my finger and swirled it in a pool of cum and brought it to my mouth. It was okay but not great by any means. I kept doing it and eventually it became a routine that I liked. I fantasized about sucking someone else as I tasted myself.

Eventually I decided that for me to experience something closer to reality I would need to cum directly in my mouth. It took a few tries of flipping my legs over my head to aim right and cum in my mouth, and it took a few more tries for me to not be afraid of it. Probably about the sixth time is when I swallowed what was in my mouth and didn't have any gag reflex. My gag reflex wasn't triggered by the taste. The taste wasn't that bad. It was more about getting over a mental block that it is okay to swallow cum.

Finally I got to the point where I was ready to see if I could meet Sonia. She had a phone number to call to make appointments. One Sunday afternoon when I was masturbating I decided to make a call expecting I would not reach her and would have to leave a message.

She answered! "Hello, this is Sonia."

"Uh, hi. I saw your advertisement on the web and I wanted to see if I could make an appointment."

"Okay Sweetie, tell me about you. Where are you from and what do you do?" Her voice was very soft-spoken and feminine sounding. I really couldn't tell the difference from a female voice.

"I'm John and I'm local, recently divorced, and I work in the telecommunications industry as an engineer."

"I see, so what are you interested in? What are your fantasies?"

"I'm new to this, my first time actually."

"That's okay Sweetie. So what do you fantasize about?"

"I have read some of your reviews online and I fantasize about what they write about. I like that you are fully functional and exceptionally beautiful."

"Thank you, Sweetie. I do lots of things so it's hard for me to know what you are talking about. Can you be more specific?"

"Well I read some reviews that you like to be on top, so I like that. I really liked one review where you took charge and made the guy suck you off and that you came multiple times for him."

"That's interesting. I think I know what you are talking about. Would you like me to take charge of our date?"

"I think that would be best."

"I like being in charge," she laughed. "Do you have any experience being with men or with a transgender woman before?

"No to both, but I've experimented with myself."

"What do mean?"

"Um, you know, I've jacked off and tasted myself."

She laughed as though she was amused with the conversation. "How many times, and do you like it?

"I've done it several times. I worked my way into it and I do like it. I think about it a lot, mostly when I am masturbating."

"That's very kinky, Sweetie," she said with a slight giggle. "I like doing that too. Have you ever eaten your whole load?"

"Mostly, I guess." I started having visions of her in my mouth as I answered. "I've tried to cum in my mouth directly several times and sometimes I hit the target. I've also tried licking it from my hand."

"Ooh, I like that. Did you swallow it or spit? I hope you don't mind all the questions. I'm just fascinated with straight guys who try this and like it."

"I don't mind the questions. I've actually never talked with anyone about this before so it's a little embarrassing. At first I spit but now I swallow most of the time."

"That's great!" she said with enthusiasm. "I hope you like it because I find it intoxicating. So is your fantasy to do what you just described?"

"I would like to try it with someone else."

"Interesting. Okay Sweetie, what day would you like to meet me? I can meet a week from Wednesday."

"Is Friday or Saturday available?"

"Not for several weeks. I can meet a week from Wednesday at 10PM. Or we can push it out if you need to meet on a Friday or Saturday. Wednesday's are better for what you are looking for. How long do you want to spend on our date?"

"Wednesday is fine. Do a couple hours seem right?"

"That sounds perfect." She got my email address and said she would email me the address of her place.

"Perfect. I'll see you then," she said. "Don't forget the test results. It's mentioned on my website."

I hung up the phone. I could not believe I had that phone call and reserved time with an escort. I was shaking with nervousness and continued my jerkoff session while looking at photos of Sonia. When I was ready to cum I opened my other hand and tried to cum on my palm. The few first spurts hit my laptop screen and then the remainder I was able to catch in my hand. "Shit," I thought. I really didn't want cum to get on my laptop. I looked at my hand and thought about possibly getting a chance to suck off Sonia. I needed to prepare. I looked at my hand again and moved my face down to my hand and took a big lick. I then looked in the mirror behind my desk and saw my tongue coated in cum and then swallowed it. Not too bad I thought. I can do this.

The next day I made an appointment to get tested at a clinic. Also, to prepare for potential penetration, I purchased a couple penis dildos from a local sex shop and tried working one of them into my ass a few times to get used to having something in there. That took some doing but I was able to finally get the entire thing in by the weekend. I also tried sucking the other dildo so that I could get used to having something like that in my mouth. And just the day before my appointment with Sonia I did some manscaping and shaved my genital area. I normally keep my hair short and tidy but I felt being shaved would be the most appealing.

Finally Wednesday came. When I got home from work I showered and got ready. I was again shaking and nervous. At one point I almost chickened out and thought up excuses not to go, but then I looked at pictures of Sonia again on the internet and decided to go for it. I could just give her the donation and then leave if I wanted to back out.

Sonia's apartment or place of work was very nice and seemed upscale. From the outside you would have no idea that this is the place an escort invites her clients. I walked up to the door and rang the bell. The door opened. Sonia stood before me in a short black silk robe and high heels. Her blonde hair was tied up behind her head and she had thin bangs reaching just to the tops of her eyes. Her lips looked moist and almost a natural color, and she had something shiny on her face and neck like tiny little sparkles, but not overly done. She looked incredibly sexy. Her legs looked very tone and slightly muscular, and her feet were sexy and small with red-painted toenails that matched her fingernails.

"Hi, I'm John. We talked a week ago Sunday."

She looked me up and down. "Wow, you are cute," she said with a big smile. "Come in." She extended her hand and I reached forward and took it. Her hand was soft and warm.

I stepped inside and there was a small narrow foyer. To the right just past the door was a cushioned bench. Across from the bench to my left were coat hooks on the wall and a small table to the right of the hooks. Above the table was a picture of Paris. There was a jar on the table that said "donations welcome." Opposite the door on the opposite wall was a large wall mirror, and to the left of the mirror was an entrance into her apartment.

"Have a seat, Sweetie."

"Sure." I sat down and she sat down to my right. She grabbed my right hand and put it in her lap and held it.

"How are you feeling? Nervous?"

"Yeah, a little," I said. I felt myself trembling.

"You have nothing to worry about. If there is anything you don't feel comfortable with just let me know. You still want me to direct our date, right?"

"Yes, if you don't mind."

"Mind? Ha! I definitely don't mind," she said with a slight laugh and smile. "I remember what you said you wanted, so if that has changed let me know."


"Did you bring your test results?"

It was folded inside the chest pocket of my jacket. "Oh yeah, it's right here." I pulled out the form which had clean results. She looked at it briefly.

"Good. Thanks for doing that. I have to be careful, you know." She folded the paper and reached inside my jacket and inserted the paper in my pocket and then I felt her fingers and palm on my chest. She squeezed my left pectoral muscle. "Ooh, you are strong," she said. "I like strong men. Why don't you hang your coat there and come inside in a minute. I'll just get ready."

She stood up and walked toward the door and then turned to face me. She was really cute! I couldn't believe how sexy she looked in person. I thought she was beautiful in the photos already and they evidently weren't enhanced. Her robe had opened partially and I could see her beautiful cleavage and something black underneath. The bottom of her robe was just barely below her crotch and I noticed how well tanned and firm her legs were. Sonia winked and then stepped through the door out of site.

I stood up and thought that this is the time to call it off if I'm going to. But I didn't want to call it off. I had gone this far I had to see it through. Sonia seemed nice and it was worth finding out more. I took off my jacket and hung it on one of the hooks. I then looked down at the donations jar and decided it would be best to put money in the jar now rather than later. I paid the suggested donation specified on her website and added a good tip on top of it. I wasn't worried about the money, so if I left early she deserved the full amount anyway for taking the risk to meet with me. Next to the jar in a picture frame were her test results from last week. Her name was listed as Sonia and the rest was hidden by a sticker over the glass.

I turned to face the mirror and looked at myself. My button-up shirt was buttoned all the way up except for the top button and I decided to open another button to look more relaxed. Had it been a minute yet? I waited for a little while longer and then stepped toward the door.

When I got to the door she was standing inside and to my right, smiling. She twirled around for me and then stopped facing me again. Her robe was removed and she was wearing a black fishnet babydoll with a deep plunging neckline that barley contained her firm breasts. The sides were open with straps wrapping around her back, and the bottom just barely concealed her matching tiny little panties. She still had on the black strappy high-heel sandals.

Behind her were French doors that were open and I could see a king size bed in the bedroom with a silky white sheet. There was a chair just outside the bedroom.

Straight ahead was a small living area with a couch and two love seats with end tables, and to my left was her kitchen.

Sonia stepped toward me walking sexily. The fishnet looked like 3/8 inch holes and her hard brownish nipples were poking through the fabric. I couldn't help but stare.

"Hey sexy," she said as she approached slowly. I turned to face her as she stopped in front of me. "Do you like my outfit?"

"Ha, yeah I love it. You look amazing." I was surprised by the question because she looked incredible.

Sonia smiled. "So why did you come to see me, John?" I hesitated, still stunned by her beauty, and was lost for words. "Do you want a big juicy cock?"

"Yes," I said. She stepped closer so that she was almost touching me with her body.

"I remember what you said on the phone. You like tasting yourself." She smiled as she looked into my eyes and brought her face closer to mine. "I think that is so hot," she almost whispered as she ran her tongue over her lips. "I love the taste of my cum."

I felt my cock start to stiffen and I was incredibly turned on by her sexiness. She grabbed my hand and led me to the middle of the room closer to her bedroom. She turned and then unbuttoned my shirt and placed her hands on my chest. "Ooh, you are sexy," she purred as she squeezed my pectoral muscles again. Then she let her fingers trail down across my nipples and to my belly. She poked me with her fingers. "I love your tight abs too." She raised her hands and pulled my shirt off of my shoulders and arms and threw it over to the couch.

"You have a sexy body. I want to lick you all over," she said giggling.

"You're beautiful," I said. It was all I could manage to say since I was stunned by how hot she was. I stared at her firm breasts and her nipples poking through her fishnet outfit. I wanted to take one in my mouth.

"Thank you, Sweetie." She stroked my chest again and then moved in to kiss me on the mouth.

"You are nervous," Sonia said. "Relax Sweetie. She kissed me again. Her tongue probed my lips and then I let it enter my mouth. It was just like kissing a girl and I began to relax a little. After a minute or two she stopped kissing me and slid one of her hands down to the front of my pants and squeezed my semi-hard cock.

"What do you have here?" she asked looking up at me smiling.

"Uh," I was incredibly slow to respond.

"It seems like you are getting a little excited. What do you want to do about that?" She smiled devilishly as she looked into my eyes.

"I want to fuck you."

"I see. That may be a possibility," she giggled. "You also want to be fucked, don't you?"


"Good, because I was planning on it. But first you are going to please me, Sweetie." She pulled both of her breasts out of her top and grabbed my hands and put them on her. "Do you like how they feel?"

"They feel amazing." I squeezed them gently and could tell she liked it.

"Don't worry, you won't hurt me. "Feel them."

I squeezed harder and ran my thumb over her nipples and they became even harder. "Mmmm, that feels so nice, Sweetie."

She reached forward and unzipped my pants. "Remove these."

I took my hands off of her and removed my shoes and pants. "Socks too," she said.

I took off my socks and threw them aside. She then massaged my cock through my boxer briefs. "It feels very big, Sweetie. I can't wait to see it."

"I can't wait to show it to you," I said laughing. Sonia laughed as well and then returned to her more serious face.

She took my hand and placed it on the front of her panties and said, "Touch me." I felt a slight bulge, but not what I expected. I think it was folded between her legs.

She dropped to her knees and pulled my shorts down. My cock was pointing straight at her face. She reached for it and stroked it a few times and then kissed it and nibbled on the shaft. "God, Sweetie. You are so big! And I love that you shaved yourself. I can't wait to play with this later," she said with an amused look on her face.

Later, I thought? She stood up and kissed me on the lips again and explored my mouth with her tongue. I used my hands to rub her bare back and explore as much of her body as I could reach, and then she stopped kissing me. She walked over to the chair by her bedroom door, faced me, and removed her panties. Her cock sprung out from between her legs and pointed down. It was large and circumcised as I expected from her pictures. She was also completely shaved. She sat down.

"Come here, Sweetie." I came over to the chair and stood before her completely naked.

"Get on your knees and take my shoes off, please." I looked down at her feet. They were as sexy as any girl I had been with. I got on my knees and she lifted one foot to my lap. I took it in my hands and found the buckle to release the straps. She then used her toes to nudge my cock and keep it stiff. She lifted her other foot to my lap and I removed the shoe.

Sonia then used both of her feet to massage my cock briefly and I felt myself get very hard. I placed my hands underneath her legs and lightly stroked her calves as she used her toes to stroke me.

"You are so hard, Sweetie. Wow."

"That feels good," I said as I looked into her eyes briefly. I then let my gaze move down her body to her sexy tits, her flat belly, and then down to her cock which was still dangling between her legs. It was probably 5 inches and mostly still soft. I had never been in front of another cock like this before. The closest I had been to another cock previously was in a locker room shower when I played sports, but I never looked at anybody then. I realized I was staring and moved my gaze back up to Sonia's eyes.

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byLuv2pleees© 12 comments/ 43667 views/ 68 favorites

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