My future wife

The last couple years of my life I have not really had a steady girlfriend. I’ve seen some girls off and on but nothing lasting longer than a month or so. I haven’t had the sexual desire to find a girlfriend with all the sexual encounters I have been having with my gardener or neighbors. However I was missing the companionship that having a girlfriend brings.

There is this girl at my office that I have been pretty good friends with at work for the past few years. Her name is Samantha but we all call her Sam. We go to lunch on occasion and I have hung out with her in a group setting outside of work a couple of times, but never just the two of us outside of work. She is a pretty cool girl that shares a lot of the same interests as I do in sports, electronics, humor, etc. I have always found her attractive but never acted on it because we worked so closely.

One day Sam and I went to lunch at our favorite spot near our office. We had a typical lunch where we mixed talk about work with talk about what’s going on in our lives outside of work. Inevitably the conversation turned to relationships. I asked her if she was seeing anyone and she said that she had been single for the past 6 months. I told her that was surprising that someone with all that she has going for her to be single that long and she blushed a little and then exclaimed that she had talked to a few guys but she just wasn’t interested.

She then asked me if I was still seeing that one girl and I replied that I stopped seeing her a couple months ago. She looked surprised and then I could see a little excitement in her face but she said nothing other than a simple "Oh". After seeing her reaction to me being single I really wanted to ask her out but I prevented myself from doing so for the same reasons I had not done so to this point.

We sat there in awkward silence for a few minutes. She kept looking at me as if waiting for me to say something and I was so nervous I just kept avoiding eye contact. We wrapped up our lunch, I paid the bill and we headed back to the office.

Once we were in the car I immediately turned the radio on in order to avoid the now lingering silence. We drove for a few minutes and I turned the radio down. I said "Sam" and her head whipped around to look at me and with a happy yet curious look in her eye she eagerly replied "Yes?" I hesitated for a second and then with a shaky voice I asked her "Would you like to go out to dinner sometime?" Before I could even finish the sentence she burst out a "Yes!" and was doing this little hoppy bounce thing in the car seat while clapping her hands and she tells me that she has been waiting so long for me to ask her at.

At this point I am smiling from ear to ear and so is she. She immediately starts asking when and where we were going to go. I asked her is Friday of that week was good and she said she was available any night. I replied "Any night?" and she nodded her head yes. So I said "How about tonight then?" She gave me this look of surprise and then pure joy and said she would love to go tonight. I told her to wear something nice but not too formal and that I would pick her up around 7pm. She was so happy that she leaned over, gave me a peck on the cheek and said she couldn’t wait.

When we got back to the office I then had to find someplace to go. I was able to get a reservation for Ruth’s Chris that night at 8pm. She loves steak and I knew she had never been there so I was hoping she would enjoy. Time came for us to all go home and on her way out she walked by my cubicle, waved and mouthed the words "See you later tonight."

I logged off my PC jumped in the car and headed home. Once I got home I took a quick shower and threw on my nice jeans and a button down and headed back out. In all the excitement I had forgot to get her address. I knew the general area where she lived but not an exact address. When I got in the car I texted her saying I was on the way and for her to text me her address. She replied with her address and said "see ya in 30!"

I was starting to get really nervous as I hadn’t been on a date with someone I really liked in a while and I didn’t want to screw it up. I finally pulled up to her house and turned the car off. I got out and was walking up to her door when the door flung open and she came almost running out towards me and practically slammed into me to give me a hug. I hugged her back and told her she looked phenomenal which she did. She had the best legs and ass and the high heels and skin tight jeans she was wearing were driving me crazy. She had on this cute little top with a leather jacket and her long auburn hair pulled back into a pony tail which is my favorite.

Once we finished hugging she ran back to her door and locked it and came back to where I was standing. I walked her back to the car and opened her door for her and she got in. I got in the driver’s seat and we took off. She asked where we were going and I told her we were going to Ruth’s Chris. She turned to me with her eyes all big and asked "Really?" I said yes and she said that she was so excited and that she’s never been. I told her that is why I picked it and she blushed and said "You remember that?" I told her of course I did and she gave me this beautiful smile.

The drive to the restaurant was about 15 minutes so we just chatted about how our days went. As we were getting closer I told her that she looked absolutely beautiful and she again just blushed and seemed embarrassed. She replied back that I looked very handsome and that she wished I dressed like that more often (we are casual dress at our work so I typically just wear jeans and a polo).

We finally arrived at our destination and I got out of the car and opened her door for her. We headed inside and since we were a little early we decided to have a drink at the bar while we waited. I ordered us a couple of martinis and we went back to talking. Instead of talking about work I wanted to start getting to know more about her. Even though since we have been work friends for some time and I know a lot about her there was still a lot I didn’t know.

After about 15 minutes the hostess came over and took us to our table. We were both still working on our martinis so we took them with us. We were seated and I ordered us a bottle of wine. We decided what we were going to eat and we ordered our food. We went back to talking about ourselves until dinner came. The night pretty much continued on like this for about an hour and a half. We were both having so much fun that we were both surprised when one of us looked at our watch at how long we had been there and that it just seemed to fly by. I only had one glass of wine because I was driving and so did Sam.

We began talking about what we wanted to do next and Sam immediately asked if I wanted to come back and watch a movie at her place. I said it sounded like a great idea so we headed out. When we got back to the car I opened the door for her and as she passed by me to get in the car she gave me another peck on the cheek and thanked me for the lovely dinner. I told her it was my pleasure and we both got in the car and drove back to her place.

When I got there she told me to park in the driveway so I did so and we got out of the car and headed in. When we got inside she told me to make myself at home and asked if I wanted anything to drink. I asked I would take a glass of water if possible. She said no problem and I sat on the couch. She came back into the room, placed two glasses of water on the coffee table and sat down next to me on the couch. She fired up the TV and then opened the Netflix app. She asked if I had a preference of what I wanted to watch and I said that it didn’t matter, I was up for anything.

She searched and searched and couldn’t find anything. She checked the movie channels on her cable and we settled on Pitch Perfect (I know, I know). Once the movie was starting she got up, turned off the light and came back and sat back next to me on the couch. This time she was right against me and we were touching. I took the cue and I lifted my arm and put it around her and she leaned against me and put her head on my shoulder. We watched the movie for about 15 minutes like this before she lifted her head up. I turned my head to see if she was alright and she was just looking at me. I knew what that look was so I took my hand that was behind her head and I gently pulled her in towards me and we began to kiss.

We were kissing softly at first but Sam began to get more aggressive. I wasn’t about to stop so I went with it. All of a sudden she pushes away and she is looking down and won’t look at me. I immediately ask if she is ok and whether I did something wrong and she begins to tear up. I turn her towards me and I ask what’s wrong. In a soft voice as she tries to hold back tears she says she has to tell me something. I tell her to not cry and again to tell me what is wrong. She finally looks up at me and she tells me not to be mad and that if I wanted to leave she would understand. I told her that I was not leaving.

She sat there in silence as if contemplating whether to tell me or not and she finally says "I’m transsexual." At first it caught me off guard not because the thought of her being transsexual was a problem, but because I was floored that I had no idea that this person I was friends with the past handful of years was transsexual. My initial reply was "Really?" She immediately took this as not a good reply and she began profusely apologizing and saying that she promises not to tell anyone at the office that we even went out to dinner. I leaned over, kissed her to get her to stop apologizing and then pulled away. I told her that I didn’t care that she was transsexual. I liked her and it didn’t matter.

I felt that since she had revealed something so big like that to me that I told her that I was bisexual. It was her turn to look surprised. She asked if I had been with a woman like her and I said that I had only been with a couple of men other than the women I had been with (she didn’t need to know the truth about how many men). She asked if I ever dated a man and I said that I am not physically or emotionally attracted to men but that it is more of a sexual thing.

I wiped the tears from her eyes and told her again that I have liked her for a long time and that I could care less about anything else. She just smiled at me with her big beautiful eyes and she leaned in and kissed me again. As we were kissing she swung her leg over me and was now on top of me in a mounted position. We continued to kiss and she again pulled back. I made a little joke as asked "What else you got for me?" She gave a little chuckle and said "No, that’s not it." She then tells me "I really like you and I would like this to not just be a one night thing or a physical thing." I replied that I feel the same way. I then asked her if she wanted to stop that I would be ok with that but if she doesn’t want to stop I reassured her that it wouldn’t change a thing about the way I view her or feel about her.

Satisfied with my answer she began to take her shirt off and then I reached around and helped her with her bra. She had beautiful little breasts. She seemed shy about me seeing them and apologized that they weren’t bigger. She said that she is on hormones but that she doesn’t want to have surgery to get implants so that this as big as they would probably get. I told her that I thought they were perfect and that I fully agreed with her decision. She then reached down and pulled my shirt off as well. She leaned in and began kissing my chest with the occasional nipple bite.

By now we were both getting aroused and I was starting to get a bulge and I could feel hers starting to form as well. We went back to kissing and now she was starting to grind against me a little. The more and more she did the harder we both were getting. She could tell we were both starting to get a little uncomfortable with our erections being restricted by our jeans so she got up off of me, grabbed my hand and told me to follow her.

I stood up from the couch and she walked me down the hallway to her bedroom. Once we got into the room she turned me so that my back was against the bed and she pushed me back onto it. I sat up and then she pushed my upper body back down and began to undo my belt and pants. While she was doing this I managed to kick off my shoes and socks so that she could get the pants completely off. Within no time she managed to have my jeans completely off and then she returned back for my boxers which were hiding my massive erection. She pulled my boxers off, flung them to the side and went straight for my cock.

She took the head into her mouth and played with it with her tongue for a few minutes. She knew what she was doing. It might have had a little to do with the fact that I really liked her, but everything she did felt amazing. She did this thing where she would turn her head sideways and take the shaft of my cock in her mouth and then run her mouth up and down the shaft while massaging my balls. She would always return to the head and give it a little attention. This whole time I was laying back but propping myself up with my elbows. We just stared at each other while she did all this. She was phenomenal.

After about 5 minutes of this she stood up and began to unzip her jeans. She asked if I was ready and I nodded yes with a smile. She very sexily, like a strip tease, began to move her hips to whatever music was in her head and began to slowly remove her jeans. With a minute or so she was fully out of her jeans and she was standing there in front of me with these cute little lacey boy shorts on and I could see her erection trying to escape. I sat up on the edge of the bed and pulled her closer to me. I began sucking on her breasts and kissing all over her upper body.

As I was doing this she was moaning softly and I could feel her goose bumps as slowly made my way down to her waist. When I had finally kissed my way down to her panties, I slowly began to peel them off revealing the perfect little cock that you would hope for. I gave it a little kiss on the head and it jumped. I then began to kiss all around her pelvic area occasionally returned to tease her cock. I finally stopped teasing her and I took her cock in mouth. She let out this little groan and I could feel her body relax. I reached around and took each of her ass cheeks in a hand and was squeezing them while I gave her head. After a few minutes she began to slowly and gently thrust her hips forward and back.

I was not ready for her to cum yet and I could feel that she was starting to get close so I stopped sucking her and as I held her I laid back on the bed pulling her on top of me. She laid there on top of me and we just kissed as both our cocks were pressed against each other between our bodies. She felt this as well and while we kissed she slowly moved her body ever so slightly up and down rubbing them against each other.

The edge of the bed was begging to cut into the back of my legs a little so with her still on top of me I managed to scoot the both of us up towards the head of the bed until our bodies were completely on the bed. We kissed like this for a couple of more minutes and then she kind of swung her legs around and then sat on my legs straddling me just below by cock. She scooted back up towards my cock a little until they were both touching and then she took both of her hands and began stroking our cocks as if they were a single cock.

She leaned forward, gave me a kiss and then whispered to me that she wanted me inside of her. She got into a squatting position above me cock with her back towards me. I put some spit into my hand and began to stroke my cock to get it wet and she did the same thing but began to finger her ass with her spit. Once she was satisfied that we were both ready, she reached down, took my shaft in her hand and guided my cock to her cute little ass. Once she found the target she eased down onto it until the head disappeared inside her. She paused for a minute and to my surprise she was much tighter than I had expected. I am not a big guy (average length) but I have a fairly large head and she was having a little trouble with it.

She lifted up off of my cock and reached over to the night stand by her bed and pulled a small bottle of lubrication from the drawer. She put a small amount in her hand and began to massage it into her ass and then rubbed the excess amount on my cock. She repeated what she did the first time and slowly inserted the head of my cock into her ass and this time it went in a little easier. Once I was in I could see her get goose bumps again this time all down her back. I reach up and began to rub her back and I could feel a little tension leave her body. She slowly started to lift up and then ease back down onto my cock. Every fourth to fifth time she would push herself a little further down and each time she would let out a little sexy whimper. I was letting her go at her own pace and I didn’t want to push it so I just continued to rub her back and hips.

As she felt a little more at ease she began to get further and further down my cock at a quicker pace. Within no time I was fully inside of her and she began to pick up the pace of her movements. I sat up and put some pillows behind my back to prop me up a little and then she leaned back and laid on my chest. I took her by the hips and I began to take more control of the thrusts and movements. She moved her upper body to the side a little so that we could kiss while in this position.

I have been in this position many times (mainly with my neighbor as she loves this position) but this was special. After a few minutes Sam stood up and turned around. She lowered herself back down onto my cock and this time slowly eased my cock all the way into her on one thrust. She began to bounce up and down and we proceeded to kiss. As we kissed I could feel her cock rubbing in between our bodies as she moved up and down my cock. I could feel the pre-cum coming out of her cock as it was making our stomachs sticky.

I wrapped my arm around her and sat up. I then leaned forward and laid her on her back. I adjusted my legs so that they were behind me and she went into an almost a perfect splits. I leaned forward and place an arm on either side of her body then with one arm reached back and placed my cock in her. I slowly pushed my cock until it was all the way in. I began to slowly thrust and I leaned in and started kissing her again. I could tell she liked this position more as I was beginning to get more groans and whimpers with every thrust. The more she reacted the harder I began to thrust.

At this point I we were going at it pretty hard. She wrapped her legs around me and whispered to me to fuck her hard. She didn’t need to tell me twice and I began to thrust as hard and as fast as I could. Her moans and whimpers quickly turned into borderline screams. Every inward thrust that I made she would release a yelp from her mouth. She was starting to become very vocal and it was turning me on even more. Within seconds she began to scream that she was going to cum and I kept pumping as hard as I could. I was thrusting so hard that the bed was violently shaking and slamming into the wall. At one point a picture frame of her and her dog fell over on the night stand but she didn’t pay it any attention.

All of a sudden I could feel her ass tighten around my cock as I pumped and then she began to cum on her stomach. Her screams began to turn into load groans and then I could feel myself reaching climax as well. I said that I was going to come and she told me to come inside her. With just a handful more pumps I began to grunt loudly as I pumped her tight ass full of cum. I kept pumping and pumping until I had nothing left in me. Once I had finished cumming I leaned forward and we began to passionately kiss. We kissed until I became completely limp and fell out of her. Once I fell out I rolled over and onto my back and laid next to her. We both turned our heads towards each other and just smiled as we stared into each other’s eyes.

I gave her a kiss and I noticed that she was starting to tear up. I asked her if everything was ok and she replied that everything is perfect. She asked what the tears were for and she said that she had dreamt about this for so long that she thought it would never happen and now that it has she said it played out better than anything she could have imagined. I told her I too had wanted to be with her for a long time but I allowed work to stop me from making any move. She was glad that I finally decided to and that she was extremely happy.

We talked about us and the situation for the next 30 minutes or so and we decided that we would keep it a secret from the people at work for the time being and if things got serious we would have to let our bosses know. I asked if anyone at work knew she was a transsexual and she said no one knew. She reassured me that if someone found out that she would make sure that they didn’t know we were seeing each other. I told her it didn’t matter and that it was up to her when people found out and if they know about us so be it, I didn’t care what they think. She gave me a kiss and then rolled over and backed her body up against mine. I wrapped my arms around her and we laid there until we fell asl**p.

Morning came and we were woken by her alarm. She reached out, shut it off and then rolled over to face me. We were both on our sides facing each other and in the cutest voice she said "Good morning". I gave her a quick kiss on the lips and said "Good morning beautiful." She pulled herself in towards my body and we both wrapped our arms around each other and laid there just holding each other’s naked body.

After about 10 minutes Sam asks "Do we really have to go to work?" I smile and tell her that didn’t know about her but I can call in sick if need be. She is silent for a few seconds and I could tell that she was thinking. Finally she says that she thinks she has nothing to do today and that she might be able to call in sick as well. She gets up out of bed and retrieves her phone from her purse in the other room and comes back into the bedroom and jumps on the bed. After a few minutes of playing with it she exclaims in an excited voice "Yep, I have no meetings!" So she begins to type on her phone and in a few seconds says "There, I just sent an email saying I’m out sick." I ask if I can use her phone and she hands it to me and I log into my email and send a similar email to my boss. I hand her back her phone and say "Looks like we both got nothing to do today." She lets out a "Yippee!" and plops back down next to me on the bed.

She begins to kiss me and in between kisses asks me what I want to do today. I tell her that this was her day and that anything she wanted to do we were going to do. She lays back and looks at the ceiling for a few minutes pondering what to do and then she asks me "Do you know what it means to be versatile?" I said of course I know what versatile means. She asks "Do you know what it means in regards to transsexuals." I wasn’t quite sure what she meant so I said "Not really." She explained that it means that the person likes to be the receiver but also the giver. She says "I’m versatile. Is that something that interests you?" I told her that I would be more than willing to do that whenever she wanted. She got this big smile on her face and gave me a kiss.

We laid there for a few minutes in silence and then she jumped up out of bed again and said she had to use the restroom. I watched her perky little ass as she walked away and as she disappeared into the restroom I could feel my cock start to stir. I go up as well and yelled out that I was going to use the other restroom and that I’d be right back.

When she finished she came by the restroom out front and obviously since I wasn’t out yet she knew I was not peeing. She gently knocked on the door and told me that if I wanted, there was a disposable enema kit under the sink. I knew what she was hinting at so when I was done I used the kit to clean myself up.

When I was done I headed back to her room and I could hear the water running in the bathroom. At first I thought it was the sink but I quickly realized that it was too loud and that it was the shower. I laid on the bed when all of a sudden she appeared from the bathroom. She didn’t say a word, she just did the "come here" motion with her finger. I jumped up off the bed and walked over to her. She put out her hand, I took hold of it and she pulled me into the bathroom and closed the door behind us.

She had a huge master bath. She had a very large shower with a built in seat and a hot tub. She had the shower running and she pulled me into the shower and closed the glass door. It was a pretty nice setup as the sinks and mirror were opposite the shower and since it had crystal clear doors and walls you could watch everything that was going on in the shower through the mirror.

Once we were in the shower we both stood under the stream of water and kissed until we both were completely covered with water. She reached over to the rail and grabbed the washcloth that was hanging from it and began to soap it up. Once it was full of suds she began to wash me. I have taken many showers with a girl before but never did one wash me before. I found it very arousing to be taken care of like that. She washed me from head to toe and then handed me the washcloth. I followed her lead and I washed her from head to toe as well. Once we were both completely soaped up we again returned to the middle of the shower and held each other and kissed under the water until all soap was gone. She then reached over and grabbed the soap and gave it a squeeze. She put it down and then from behind me she reached around and began stroking my cock. I was hard in no time flat and I could feel that she was starting to get erect as well as her cock was starting to poke into the bottom of my ass cheek.

After a minute or two of this I too reached over and got some soap in my hand and I turned her around so that she was facing away from me. I reached around and began stroking her cock. While doing this I got down on one knee and began to eat her ass while stroking her. She began to moan and grind her ass against my face. We did this for a few minutes and then she turned around, put her hand under my chin and then lifted letting me know to stand up. We kissed and then she whispered in my ear "Can we do what we talked about earlier?" I looked her in the eye and said, "You don’t need to ask me that ever. If that’s what you want to do then that’s what we will do." She grabbed me and gave me a big kiss."

Once she let go I turned around and put my hands on the shower seat and then bent at the knees a little since she is shorter than me. She got down on her knees and as I did with her, she began to eat my ass. While eating my ass she began to slip a finger or two into to loosen it up. Like the night before, this is nothing new to me, but my feelings for this girl were making it all the more enjoyable. After a minute or so she stood up and placed a hand on my ass. With her other hand she took her cock and guided it to my ass. She inserted the head of her cock into me and realizing that there would be no resistance she quickly inserted her cock all the way inside of me. She was of average length and girth but she knew how to use it. As she thrusted she would make these little swirls and movements that was hitting certain spots inside me that would give me pleasure.

We were in this position for a couple of minutes and then she turned around and sat on the shower seat. We stayed in the same orientation so I was facing away from her and sitting on her cock. I began to bounce up and down on her as she guided me holding onto my hips. While in this position she would run her nails up and down my back and it felt like I was in heaven. I took my cock in my hand and I began stroking it as I was so excited and filled with pleasure.

By now she was holding my hips up off of her and she had begun upward thrusts into me. She was pumping in and out of me and I matched the strokes of my cock to the rhythm of her thrusts. In a matter of minutes I yelled out that I was going to cum and she began to fuck me even harder. As she thrusted in and out of me I began shooting my load all over the shower floor. I kept jerking as I watched my cum circle around and then finally disappear down the drain.

I collapsed into her lap as I recovered from cumming and then she stood up and told me to lay on my back. It was a huge shower so I was able to lay almost full length; I just had to put my feet up a little around the seat. Sam got down on her knees and I lifted my ass in the air giving her easier access. She took her hand and lifted my ass up higher and with the other hand placed her cock back in my ass. She leaned forward and placed her arms on either side of me and we kissed as she began to slowly fuck me again.

As we lay there on the floor of the shower and my dream girlfriend was fucking me I just kept thinking about how excited and lucky I was to be with her. The further along we went the hard and harder she began to thrust. A couple minutes in she sat in a more upright position and just began to jackhammer me. She hooked my legs with her hands and as she was thrusting into me, she would pull me towards her increasing the f***e of each thrust.

I could tell she was getting ready to cum because like the night before she began to get really loud on the verge of screaming. She was thrusting with all her might and then with a yell of "I’m cumming!" she thrusted and then stayed all the way inside of me as she pumped load after load of cum into me. Every spurt was accompanied by a yelp and then eventually the yelping and cumming stopped. She then continued thrusting for a few more seconds until she went limp and couldn’t stay inside me anymore. She leaned back against the bench and let out this big sigh.

She reached down and began to finger my ass facilitating her cum draining from my ass. I pushed a little as well to help and eventually it all drained out into the shower and down the drain. I sat up and moved next to her up against the bench. I put my arm around her and she leaned against me and put her head on my shoulder. We sat there with the water hitting us for about another 15 minutes until the water started to get cold.

We got out of the shower and toweled each other off and returned to the bed. We laid there for a while just holding each other and enjoying the moment. Sam eventually asked if I was hungry and I said yes. She asked if I liked pancakes and I replied "I’m a man, all men love pancakes." She chuckled and then said she would make me some. She stood up, put on some underwear and a t-shirt and then left the room. I put my boxers on and my under shirt from the night before and headed into the living room.

I helped her cook breakfast and we just sat around the house talking and relaxing all day. We have been together ever since. I think she may be the one…
100% (46/0)
 
Categories: AnalShemales
Posted by handiman1980
7 months ago    Views: 4,799
Comments (8)
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6 months ago
Great writing, I've got a serious hard on!
7 months ago
That, was a good story, one of the better ones. Nicely done.
7 months ago
great story thanks for sharing!
7 months ago
Great story, we'll written and very sexy. I'm rock hard now. Thank you.
7 months ago
Well written, loved it
p-bass
retired
7 months ago
Great story, I loved it!
7 months ago
Love it.
jimchitwo...
retired
7 months ago
A very hot and sexy story! Had me hard and stroking! Thanks!