Sara - My trans experience (Part 1)
I apologize for this will being slightly long. It is necessary to tell my story as I lived it and still vividly remember it.
It is February 2003 and as is normal with me either my sex-life / personal life or professional life is booming but rarely both at the same time. As life has it, my sex-life is non-existent for the last 6 months, but my professional career is booming having been made a partner in my company and given a huge bonus. Normally, I would just invest the money in a mutual fund to avoid any issues with work, as I already owned an apartment in Manhattan. At the urging of my good friend and mentor, he suggests that I buy a vacation place to get away from the hustle and bustle – as he is seeing me beginning to burn out as I am a workaholic and love what I do.
As luck will have it, my very first weekend looking at properties, I find a house down the NJ shore – 3 blocks from the beach, 6 blocks from downtown area and a little further to the train station. I got a steal on the property. It became a money pit for a couple that caused them to divorce. It was a corner property with a detached garage with a small apartment above it. The place was gutted to make an open concept. They were only able to complete the main bathroom and 3 bedrooms on the second floor before their very messy break-up.
I had to complete the first floor, exterior and landscaping. Re-modeling and all the issues occupied my mind on the weekends – a good mental health break, but it was proceeding very slowly.
I decided to take vacation the last two weeks of August (generally a slow time at work) to push forward to get the main floor (kitchen, living room, pantry and office) done. When I was working on the house, I had the same routine, waking up at 5:30AM and going to the local shop getting a coffee with either a muffin or bagel and read the sports section. Sometimes having small chitchat with the staff, usually the manager and high school/college students working the summer – they all knew my order and routine making jokes along the way. After my breakfast, I would return home and would start work or go to the big box hardware store for supplies or waiting for the contractors.
It was Wednesday. I busted my hump all day. I needed a caffeine fix and stopped to get a late afternoon coffee (not normal for me). Only one girl, Sara, was working, and I made a joke about “do you ever go home” since she is always opening at 5AM. She laughs and says she is starving and glad they are closing at 4:30 today. I tell her I am going to the diner for dinner and would love some company. (I was not hitting on her just really would like to talk to someone other than contractors.) Surprisingly, she says yes and says I will meet you there around 5 o’clock. I run home emptying my car of stuff for tomorrow’s projects and did some general cleanup from today’s work before heading to the diner.
I get to diner’s parking lot and at the same time, she arrived in red VW Beetle – very cute car, and she even has a flower in the dashboard vase. We make some small talk walking in. This was the first time I noticed her cute ass as we walked up the stairs. She is 23, about 5’6” with shoulder length light brown hair.
We get seated and started some general conversation – explaining what I do, my education, the house, my family (only c***d), etc. I ask about the car, and she tells me it is her aunt’s that she uses when staying and working at the coffee shop. I then ask her about her family (mother, father, brothers, sisters) – dead quiet – all I could think is that I asked the wrong question – a long awkward pause. She then takes a deep breath and asks me to promise not to tell anyone about what she is about to tell me. She tells me she is transgender (I had no fucking idea as she was very feminine, plain but attractive). She only sees her mother once or twice a year and her father disowned her (Boston catholic family). Her “aunt” was her godmother who took her in at 16, and the only one she views as family. I tell her I do not understand how anyone can stop loving and caring for a person they gave birth and raised – not in my world. I then decide to open up to her and tell her I am bisexual having both male and female experiences, and this is something I have never really disclosed to anyone in my immediate circle asking her to use her discretion. She nods and we are smiling at each other.
The conversation resumes and is flowing more naturally again. She tells me she is going into her senior years at FIT majoring in graphic design and illustration in the city. She did an internship with a shoe designer but did not like. She really wanted to explore illustration and computer design (animation) as a career. I explain that I have collection of animation cells (10-12) with the first given to me by an administrative assistant – Road Runner - since I never sit down. I added to the collection over the years. I tell her that they are at the house in boxes in my office – “you should come over and see them as they was pretty cool” and she replies – “I would like that.” We eat and the conversation is still good, a little all over the place but nice. On leaving, I ask if she wants to the see the animation stuff now – surprisingly she says yes and I tell her the address, follow me and to park in the driveway as parking may be tough during the summer months.
We arrive at the house walking up the stair together into a recently sheet-rocked room – dusty, electrical and computer wiring hanging and supplies s**ttered throughout – telling her my plans. My office is done but nothing is hanging up. I see myself in the mirror and I got dust, plaster and paint on me. I laughed asking why did you not say anything – we laughed together. I pulled out the boxes with the artwork and start to show her. I tell I really need to shower to get this stuff off me – “I will be back in five - ten minutes.” I tell her to make herself at home, there are various drinks, wine and beer in the small refrigerator, however – no real food. There are also great views of the sunrise and sunsets from the porches. She says, “Okay – go ahead.”
I run upstairs directly to the bathroom take my clothes off and take a quick shower. I get out and wrap a towel around me to go get clean clothes in the bedroom. As I turn into the bedroom, Sara is leaning against the slightly elevated bed; she is dressed only in a lacey sports-type bra and pink panties. In an instance, I pause entering the room, both of us are smiling and boom – fully erect underneath the towel. I move toward her slowly, and we start kissing and caressing.
She has small but nice tits as I lift up the bra to suck on her nipples that were very perky. She takes off the bra as I proceed to slowly drop down kissing her belly to her panties. I pull down her panties with my thumbs – at the same time my towel falls to the ground. I am leaking a lot of pre-cum. With her panties around her knees, she has a small 1.5” flaccid cock, completely shaven that I begin to suck – quickly she is aroused – a perfect 5 – 5.5 “ swollen in my mouth. I am working her slowly but she cums quickly (1-2 min.) in my mouth. I keep sucking her gently until she is flaccid. She is giggling and saying, “stop, stop, please stop.”
I stand up and we kiss as I lift her onto the bed with my two hands on her butt. We roll over with her on top of me still kissing. She proceeds slowly down my body sucking then biting my nipples. I never knew my nipples were that sensitive. It was such a turn-on. I am still rock hard as she moved down and begins to gently and slowly work me with her mouth and hand. I explode in 2-3 minutes. She slides up my chest and shares a cum kiss with me. We crawl under the covers continuing to kiss and caress each other. Finally, we are spooning and holding each other.
As we are cuddling, we both dose off for 5-10 minutes. As I am spooning her, lying on my right arm, her hair smells like coffee. I start caressing her nipples and body slowing working around to her ass and cock with my left hand, occasionally nuzzling her neck. She is very smooth. I begin working her cock head between my thumb and fingers with her pre-cum as she is softly moaning and breathing heavy. She rolls fully on her back as I slowly masturbate her and then wow – a big load all over my hand and her belly. It totally surprised me, as it was a lot larger then when she came in my mouth. We lie silent for a couple of minutes and she then reaches for the towel to clean us up. She has a big smile and just looking at me completely satisfied. She stands and gets out of bed, sayings she has a lot to complete at home and must go. I sit up and we get dressed. I watch her dress thinking what a day; walk her to the door waving as she drives off. I was thinking she was a little intimidated to have anal sex and wanted to leave. After she departs, I am horny as all hell, needing to jerk off just to get to sleep.
Unexpectedly, I sleep late to 8:30, which is a very rare occurrence. I walk to the coffee shop. No Sara. I just get my regular order and go home. I got nothing accomplished as I was thinking about her all day. On Friday, I get up at my regular time and walk to the coffee shop, no Sara again, so I ask where is she, the owner says she returned back to school. She may have mentioned it to me, but I do not recall – a little depressed all day. Once again the house renovations begin consuming me, as the electrical contractor will be showing up shortly.
To be continued ...
It is February 2003 and as is normal with me either my sex-life / personal life or professional life is booming but rarely both at the same time. As life has it, my sex-life is non-existent for the last 6 months, but my professional career is booming having been made a partner in my company and given a huge bonus. Normally, I would just invest the money in a mutual fund to avoid any issues with work, as I already owned an apartment in Manhattan. At the urging of my good friend and mentor, he suggests that I buy a vacation place to get away from the hustle and bustle – as he is seeing me beginning to burn out as I am a workaholic and love what I do.
As luck will have it, my very first weekend looking at properties, I find a house down the NJ shore – 3 blocks from the beach, 6 blocks from downtown area and a little further to the train station. I got a steal on the property. It became a money pit for a couple that caused them to divorce. It was a corner property with a detached garage with a small apartment above it. The place was gutted to make an open concept. They were only able to complete the main bathroom and 3 bedrooms on the second floor before their very messy break-up.
I had to complete the first floor, exterior and landscaping. Re-modeling and all the issues occupied my mind on the weekends – a good mental health break, but it was proceeding very slowly.
I decided to take vacation the last two weeks of August (generally a slow time at work) to push forward to get the main floor (kitchen, living room, pantry and office) done. When I was working on the house, I had the same routine, waking up at 5:30AM and going to the local shop getting a coffee with either a muffin or bagel and read the sports section. Sometimes having small chitchat with the staff, usually the manager and high school/college students working the summer – they all knew my order and routine making jokes along the way. After my breakfast, I would return home and would start work or go to the big box hardware store for supplies or waiting for the contractors.
It was Wednesday. I busted my hump all day. I needed a caffeine fix and stopped to get a late afternoon coffee (not normal for me). Only one girl, Sara, was working, and I made a joke about “do you ever go home” since she is always opening at 5AM. She laughs and says she is starving and glad they are closing at 4:30 today. I tell her I am going to the diner for dinner and would love some company. (I was not hitting on her just really would like to talk to someone other than contractors.) Surprisingly, she says yes and says I will meet you there around 5 o’clock. I run home emptying my car of stuff for tomorrow’s projects and did some general cleanup from today’s work before heading to the diner.
I get to diner’s parking lot and at the same time, she arrived in red VW Beetle – very cute car, and she even has a flower in the dashboard vase. We make some small talk walking in. This was the first time I noticed her cute ass as we walked up the stairs. She is 23, about 5’6” with shoulder length light brown hair.
We get seated and started some general conversation – explaining what I do, my education, the house, my family (only c***d), etc. I ask about the car, and she tells me it is her aunt’s that she uses when staying and working at the coffee shop. I then ask her about her family (mother, father, brothers, sisters) – dead quiet – all I could think is that I asked the wrong question – a long awkward pause. She then takes a deep breath and asks me to promise not to tell anyone about what she is about to tell me. She tells me she is transgender (I had no fucking idea as she was very feminine, plain but attractive). She only sees her mother once or twice a year and her father disowned her (Boston catholic family). Her “aunt” was her godmother who took her in at 16, and the only one she views as family. I tell her I do not understand how anyone can stop loving and caring for a person they gave birth and raised – not in my world. I then decide to open up to her and tell her I am bisexual having both male and female experiences, and this is something I have never really disclosed to anyone in my immediate circle asking her to use her discretion. She nods and we are smiling at each other.
The conversation resumes and is flowing more naturally again. She tells me she is going into her senior years at FIT majoring in graphic design and illustration in the city. She did an internship with a shoe designer but did not like. She really wanted to explore illustration and computer design (animation) as a career. I explain that I have collection of animation cells (10-12) with the first given to me by an administrative assistant – Road Runner - since I never sit down. I added to the collection over the years. I tell her that they are at the house in boxes in my office – “you should come over and see them as they was pretty cool” and she replies – “I would like that.” We eat and the conversation is still good, a little all over the place but nice. On leaving, I ask if she wants to the see the animation stuff now – surprisingly she says yes and I tell her the address, follow me and to park in the driveway as parking may be tough during the summer months.
We arrive at the house walking up the stair together into a recently sheet-rocked room – dusty, electrical and computer wiring hanging and supplies s**ttered throughout – telling her my plans. My office is done but nothing is hanging up. I see myself in the mirror and I got dust, plaster and paint on me. I laughed asking why did you not say anything – we laughed together. I pulled out the boxes with the artwork and start to show her. I tell I really need to shower to get this stuff off me – “I will be back in five - ten minutes.” I tell her to make herself at home, there are various drinks, wine and beer in the small refrigerator, however – no real food. There are also great views of the sunrise and sunsets from the porches. She says, “Okay – go ahead.”
I run upstairs directly to the bathroom take my clothes off and take a quick shower. I get out and wrap a towel around me to go get clean clothes in the bedroom. As I turn into the bedroom, Sara is leaning against the slightly elevated bed; she is dressed only in a lacey sports-type bra and pink panties. In an instance, I pause entering the room, both of us are smiling and boom – fully erect underneath the towel. I move toward her slowly, and we start kissing and caressing.
She has small but nice tits as I lift up the bra to suck on her nipples that were very perky. She takes off the bra as I proceed to slowly drop down kissing her belly to her panties. I pull down her panties with my thumbs – at the same time my towel falls to the ground. I am leaking a lot of pre-cum. With her panties around her knees, she has a small 1.5” flaccid cock, completely shaven that I begin to suck – quickly she is aroused – a perfect 5 – 5.5 “ swollen in my mouth. I am working her slowly but she cums quickly (1-2 min.) in my mouth. I keep sucking her gently until she is flaccid. She is giggling and saying, “stop, stop, please stop.”
I stand up and we kiss as I lift her onto the bed with my two hands on her butt. We roll over with her on top of me still kissing. She proceeds slowly down my body sucking then biting my nipples. I never knew my nipples were that sensitive. It was such a turn-on. I am still rock hard as she moved down and begins to gently and slowly work me with her mouth and hand. I explode in 2-3 minutes. She slides up my chest and shares a cum kiss with me. We crawl under the covers continuing to kiss and caress each other. Finally, we are spooning and holding each other.
As we are cuddling, we both dose off for 5-10 minutes. As I am spooning her, lying on my right arm, her hair smells like coffee. I start caressing her nipples and body slowing working around to her ass and cock with my left hand, occasionally nuzzling her neck. She is very smooth. I begin working her cock head between my thumb and fingers with her pre-cum as she is softly moaning and breathing heavy. She rolls fully on her back as I slowly masturbate her and then wow – a big load all over my hand and her belly. It totally surprised me, as it was a lot larger then when she came in my mouth. We lie silent for a couple of minutes and she then reaches for the towel to clean us up. She has a big smile and just looking at me completely satisfied. She stands and gets out of bed, sayings she has a lot to complete at home and must go. I sit up and we get dressed. I watch her dress thinking what a day; walk her to the door waving as she drives off. I was thinking she was a little intimidated to have anal sex and wanted to leave. After she departs, I am horny as all hell, needing to jerk off just to get to sleep.
Unexpectedly, I sleep late to 8:30, which is a very rare occurrence. I walk to the coffee shop. No Sara. I just get my regular order and go home. I got nothing accomplished as I was thinking about her all day. On Friday, I get up at my regular time and walk to the coffee shop, no Sara again, so I ask where is she, the owner says she returned back to school. She may have mentioned it to me, but I do not recall – a little depressed all day. Once again the house renovations begin consuming me, as the electrical contractor will be showing up shortly.
To be continued ...
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