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My new gurl

My new gurl

This story is pure fiction/fantasy. Nothing in this story is real, and never actually happened. If you like bd/sm, gay, dominant story, then I hope you enjoy.






My name is Thomas, or big Tom as I like to be called. I am a traveling trouble shooter for a national chain store. I travel so much, that I practically live, for the most part, out of my company paid vehicle, and motels. I travel so much, that I have never had time for a conventional relationship. I learned a long time ago, that I was actually bisexual.


Now, part of the problem with women, at least I think so, is that I stand at 6'5", weigh about 320, hardly any fat, and I am about 113/4" long by about the size of a man's wrist. I know, sounds far fetched, but I swear it's true. Hell, I had to loose my virginity to a sloppy old whore my buddies from work paid for. I am a white male, 45yrs old.

I was getting ready to head from Austin Tx, to Sault St. Marie Mich. The store there was having computer software problems, and needed me there. They won't pay for airfare, so, I drive. As I was filling my tank up, I saw this skinny looking k**, trying to catch a ride on the highway, north bound. I finished filling my tank, went in, grabbed a twelve of soda, went to the check out, paid for everything and a few packs of smokes, and a pack of cigars.

I pulled into traffic, and put my blinker on to turn. As I turned onto the on ramp, I saw a car quickly speed away from the k**. He was trying to run after the car, and looked like he was yelling at it as it sped away. He stopped swung his arms in anger, then lowered his head, and looked like he was crying. I pulled to the side of the road just before him, put my hazards on, got out and approached him. I told him my name, and asked if he was alright. He looked up at me, and I swear my heart skipped a beat.

He had sandy blonde hair that was just past the top of his shoulders, he was skinny, almost scarecrow looking in body size. His eyes, they were a medium frosty blue. He said his name was Robert, but liked to be called bob. I asked again what was wrong, and he said that he was trying to get to Michigan. I asked him where in Michigan, and he said a little town about 5 miles before sault st. marie. I looked at him stunned.

He asked if he said something wrong, and I said no, but that is where I am heading to. He also said that the car that took off had his bags in them. It also had all his money in it. I told him not to worry, and get in the car so we don't get a ticket for holding up traffic. He looked like he was going to decline, but, I gave him a stern look, and he shrugged his shoulders, and got in the car. He kept saying he didn't want to be a bother to me, but I told him I would love the company, because it got boring on long legs like this.

We had not even reached Dallas, and he was sound asleep. Because of the later start from Austin, we were coming thru Dallas about 9-9:30 at night. As we went under the lights, I was able to check him out even more. he was skinny, about 5'7", I would guess his weight at about, 135-140 at the most. I drove for another 5 hours, before I started looking for a motel sign. Another 30 minutes, and I spotted a motel sign. As I pulled in for the night, bob woke up, and asked where we were. I told him the name of the last town we had went thru, and said I was stopping for the night.

After checking in(luckily getting the last room they had), and getting my bag up into the room, I said we were going to get something to eat, and then crash for the night. He started to say he had no money, and I just sternly interrupted him, asking him if I had said anything about him paying for his food, he hung his head, and said no sir. I felt my cock throb at those words.

I said lets go. He followed me out the door, waited for me to make sure the door was locked, and after I started walking, he fell in step, just behind me. After we ate, we walked back to the room, and I told him to strip, and go take a shower. He looked like he was about to protest, when I looked at him, and in a stern voice, said did you hear me? yes sir he said with head bowed. Then do it I said. He stood up, and slowly took off his shirt first, exposing a completely hairless body. from his pants waist line, all the way up to his head hair, eyebrows, and such.

He then tried to turn away from me to take off his pants, when I told him to stay facing me as he stripped everything off. He resumed taking his pants off, his face turning a crimson color as his pale blue lacy panties came into view. I then knew what kind of a boy he was. As he took his panties off, I saw his little dick. It was only about 4" long, and it looked like he was hard. he had almost no hair around his dick. Actually, it looked like an extremely large clit.

I told him go take his shower. I watched that little ass sway going away from me, and I actually felt my cock getting rock hard. After he finished his shower, he came out with a towel wrapped around his waist. I told him to sit, watch tv, and I went, and took my shower. I was tempted to stroke one out, but decided to wait, and see what might develop. I wrapped a towel loosely around my waist, and walked out of the bathroom. I saw bob, no, bobbi, sounded more feminine to me in my head, sitting on the bed dressed again. I looked at him, and said I did not tell you to get dressed, now take them back off. He looked at me, and I looked him right in the eyes, and said I told you to take them off.

He slowly stood up, and took his cloths off again. I stepped to the bed, sat down, and as he turned to look at me, I grabbed his wrist, and pulled him face down over my knees. When I grabbed, and pulled him, he let out an adore-able little girly squeak. I put my left hand against the middle of his back to hold him down, and raised my right hand, and brought it down with only a quarter strength.

The crack when my hand hit his ass was loud to my ears. the squeal that came was not fully from the pain I thought. After each swat on his ass, there was a squeal, and now a few sobs. I also thought I was feeling something wet on my leg. After 10 swats on his cute, now red ass, I told him to sit next to me on the bed. I then told him to tell me why he was going to Michigan, and not to leave anything out.

He sat there for a moment, and then slowly started. It was about two hours later that he finished. Turns out that mom, and dad were divorced , and dad had died in a freak accident at work. His mother had remarried to a real idiot. when he found out that bob/bobbi, was gay, he forced mom to kick him out. He was on his way to his grandfathers to live. The money that was stolen, was his complete life savings, all 300 dollars.

It also turns out he was a submissive, and had to leave his part time(as he said) dom behind. I said that I will be his dom, at least until we reach his destination. I then asked him if he liked dressing in women's clothing, and he replied that he was too small, and only p*****ns, or young teens would fit. I then told him to take my towel off, and see what he is now going to have to satisfy, but to do so on his knees.

He got down off the bed, sank to his knees, and crawled between my knees. He reached up with his hands to my waist, and tugged the towel ends from each other. As he opened the towel halves, he was looking up at me with those eyes of his. when he had reached the outer limits of the spread towel, he looked down, his got wide as golf balls, he gasped real loud, as his jaw almost hit the floor. He looked back up at me with the question in his eyes. I said 11 3/4" long, and a little bigger than your wrist around.

I looked at him, and said yes, you are going to love it by the time we get there. I said you can start out slowly sucking me, to start getting used to my cock, and be able to take all of it down that throat of yours. He started licking my cock making it get to full erection. he took as much of me as he could, about 2-3 inches. He kept going for about 30 minutes, he started saying his jaw was starting to hurt. I told him as my sub, it was his responsibility to get his dom off, and that he wasn't done yet.

He said his jaw hurt too much to continue. I looked at him, and told him that he was going to become a woman a lot sooner than I had originally planned. He then looked at me with a puzzled look on his face. I then grabbed both of his hands in my left hand, and shoved a ball gag in his mouth before he could react. The ball gag had Velcro on it, so it was easier to put on. I let go of his hands, and quickly finished off putting the straps for the gag on. He was hitting me, I think with all his strength, which still felt like light slaps on my chest and arms.

I quickly grabbed his hands, and forced them behind his back, and securing them with a double wrist leather shackles. I then told him that if he relaxed, it would not hurt as much, and there would be no injuries to either of us. I then pulled him over onto the bed, trying to decide how I wanted to take him. I put him on his back, and pulled his legs apart. I found I needed to be standing on the floor next to the bed, with him on his back at the edge of the bed. I reached under my pillow, and grabbed the lube I had put there while he was in the shower.

As I lubbed up my cock, he was watching with wide eyes. I put some lube on my finger, and started to massage it into his asshole, slowly pushing my finger deeper until I reached my last knuckle. I started fucking my finger in, and out of him for a few minutes, adding a second one, and a short while later, a third finger. I fucked my fingers in, and out for 10 minutes. I re- lubbed my cock before approaching his hole with it. I looked up at his eyes, and they were staring at my cock as it slowly approached his ass.

I told him to look into my eyes, and take a few deep breaths, and relax. As I waited a few minutes, I saw his breathing getting slower, and when I felt his legs relax, I shoved my cock head thru his sphincter muscle, and stopped. He let out a squeal that was thankfully muffled by the gag, his whole body locking up. As he was like that I was rubbing the outside of his thighs, and saying soothing words to him. Every time I felt his anal muscles relax, I let slip in another inch before stopping to let him relax. It took about 20 minutes before I was buried to the hilt in his tight ass.

I waited until I felt him relax, and then started a slow, but steady in, and out rhythm. I slowly increased the speed, and stroke length, until I was pulling almost all the way out before going back in to the hilt. After going at it for about 25 minutes, I noticed his cock was hard, standing straight up, quivering, and leaking pre-cum in a very large amount. I asked him if he was liking it, and all I got was a thrust of his hips, a long drawn out moan, and his head shaking back, and forth.

I was by this time, really fucking him hard. I said out loud, bobbi my sweet little girl, daddy's cumming in your little pussy, and thrust all the way to the base, and came so hard, it hurt. I must have shot a pint of cum into her. It was coming back out around my cock. I looked down and saw that she had cum too. I slowly pulled my spent cock out, and a deluge of cum came pouring out. I looked down at her/him, and said in a soft loving voice, you are now a woman, and you should be proud, you took all of me on your first time. As I looked down into those eyes, I saw acceptance, submission, and I believe love too.

I asked if she was going to scream, try to run, and she shook her head no. I first turned her over, and released the shackles, and gently rubbed her wrists to make sure nothing was hurt. I then removed the gag from her mouth. She, wow, that's how I thought of this person in front of me. Anyway, she just wrapped her arms around my neck, and planted her lips on mine, trying to suck my tongue out by the roots.

I pulled back, and said what, and that's as far as she let me get before putting fingers to my lips. She then told me that it had always been a dream/fantasy/desire of hers to be taken by a big strong bull of a man, to be forced to submit, and to have his virginity taken. When I had started telling him what to do, he started hopping that I was going to be the one. Then when he saw my cock, and it wasn't even hard, he got scared. Then when he saw it hard, he thought that I would rip him apart.

She then went on to say, that after I was fully inside, and she relaxed, it started feeling real good, and when I started slowly fucking her, the feelings grew to every point on her body, and then when I came she said, it felt like a pleasure bomb went off in her head, and her heart, especially after I called her daddy's little girl. Every night on the trip(which I purposefully made a few days longer) she was practicing her blow job skills, perfecting them by the time we got there. She ended up traveling with me for 10 years. 10 years of bliss until 9/11, and took my bobbi away.

Yes she did start taking hormones, but never got the surgeries. she developed into a small, 5'7", 128lbs, 34b, 20 inch waist, and a 26" hips, a total sexpot. She became the love of my life.
Published by chefjohn2112
6 years ago
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grbimeat4u
grbimeat4u 6 years ago
Bobbi sounds like a dream come true
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