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Kathy Has a Surprise for Me

Graduating from high school at 18 I was off to college that fall. I was going to a community college in the nearby city in preparation for going to a more prestigious institution. My name is Greg. My grades had not been that great. I was more interested in girls than school and had made the attempt to work my way through all of the girls in high school. I must have fucked at least 20 in my class of 100. Pretty good record if I say so myself. I never stayed with one more than a night or two, especially if they wouldn't give me a blow job. I loved those more than fucking I must say. I always thought it was because they just didn't meet my standards. I later realized that I may not have met theirs.

I was not going to live in a dormitory. Mainly because this was a new college. They only had two dorms and they were full by the time I got my ass around to applying for a room there. So I went the roommate route. I checked all the bulletin boards on campus during the summer and also went to the housing authority that was kept up by student volunteers. I was having little luck until I found a notice behind several other notes on a board by the student union. It must have been covered over for weeks. It had all its little hanging tags still intact. That meant that probably no one had applied to join this person as a roommate. It was worth a shot.

I called the number on my cell phone and a girl answered. She sounded surprised and slightly relieved to hear from me, or anyone I would guess. We made an appointment I guess you would call it. Anyway I was to stop by the apartment that afternoon. I went over at the right time and was so glad I had called. This girl was gorgeous. She had short black hair cut like a pixie. She was only about 5 feet 2 inches, but she had tits that were perfect. She was wearing a cut-off t-shirt and I could see her navel. She was obviously braless and her breasts were what I always found to be perfect. They were shaped like cones, poking straight out and I could see she had the large fat nipples I loved. Her body was great, with wide hips and a fine ass. She was wearing cut-off jeans and her ass cheeks could be seen with the crease under them. And her legs were curvy and muscular. I could imagine them wrapped around my waist.

I was about 5 feet 8 inches myself with brown hair and brown eyes. I was not in great shape but I wasn't overweight or anything. I just didn't work out or that kind of thing. But I had a cock 7 inches long that some girls seemed to like a lot.

Anyway, I loved the look of Kathy. That was her name. And she was happy as hell to find someone interested in sharing the rent on the one bedroom apartment. We didn't make any big deal about sharing a room. This was the 21st century for god's sake. Besides, we both felt we were grownups. We had the bedroom and a living area with a kitchenette attached. The bathroom was off the living area, not the bedroom. Plenty of space for two young people.

Well, I moved in immediately. Classes were starting in a week and I wanted to get used to the campus as soon as I could. I already knew it pretty well but you should always know your territory like the back of your hand. I learned that in ROTC in high school. Kathy had already been there for a month so she showed me around. We were becoming good buddies and I was looking forward to testing the sexual waters soon.

I learned that she had a laptop just as I did and we were both addicted to our computers. We would both stay up late jumping from site to site. Sometimes we would do it together in our room, or one of us would stay out in the living area on one of the desks. No special routine. But sometimes when I got up from the bedroom and she was out at a desk I would notice some odd things on her computer as I passed by on my way to the bathroom. She would often attempt to hide the screen but I could tell she was on porn sites. You could always tell those. God knows I had been on enough myself.

One thing I noticed immediately the first day. She was not about to change clothes with me in the same room, either the bedroom or the living area. She kept her body to herself. Nothing really odd about that, but I had expected college students to be a little cooler about that short of thing.

Once I walked into the bedroom after having returned from the library about 10 in the evening. I wasn't creeping in or anything but I didn't make a lot of noise either. I walked into the bedroom and caught Kathy with her clothes off. The odd thing is she did nothing to hide her tits. But she was really concerned about covering her crotch with a pillow. And she expressed her huge disapproval. I apologized of course but thought nothing more about it except I had been right. Her titties were great. Like cones poking out to be sucked on.

The other odd thing was she didn't seem to care if I changed in front of her. She would not stare at me but she made no big deal out of me changing my underwear in front of her in the morning. She would glance over and then away. She would blush but she said nothing to discourage it.

Once she caught me jacking off to my computer when I was in the living area and watching some porn. This time it happened to be tranny porn. Somehow I was drawn to it occasionally. I saw nothing odd about that. Most of my buddies in high school had watched the same stuff once in a while. Anyway, she blushed but said nothing. I quickly stuffed him back inside and was checking out Facebook when she came out of the bathroom.

A couple of days later Kathy was sitting watching the tube when she suddenly spoke up. "Greg, do you mind if I ask a very personal question?"

"No, not at all. What's up roomie?"

"Well, this is embarrassing, but were you looking at transsexual porn the other night?"

"Yeah, I know, it was a little odd me doing that. Sorry if I made you nervous. I won't do it again."

"Oh, no. It doesn't bother me at all. I know guys jerk off and stuff. I was just wondering about the stuff you were watching. Do you watch it a lot?"

"Well, geez, Kathy, I watch it sometimes. Not all the time. I just get curious sometimes I guess."

"Okay, sorry to embarrass you. No big deal or anything. I don't even mind you doing it in the bedroom when I am there. It wouldn't bother me. I have three brothers. I have seen guys jerking off before. No big deal."

"Wow, Kathy, you are always surprising me. You are great. I won't really do it a lot, but thanks for the okay!"

So anyway about a week later I was on my bed looking at porn. And I was jacking off when Kathy walked in. I stopped but she just grinned and said, "Go on dude, have your fun. I told you it doesn't bother me in the least."

So I continued jerking off, and she came over to see what I was watching. It happened to be tranny porn again. Well, I liked it. Anyway, she looked at it and then she began squeezing her tits as she looked over my shoulder. I couldn't tell if she was watching the porn or my cock. Either way it was a turn on and I shot my wad into the tissues I had by the bed. She laughed and then went to the bathroom to change for bed.

Later that night as I was just drifting off to sleep I could hear her bed squeaking. I imagined she was rubbing her pussy, getting off like I had earlier. It made me hard again and I started beating off once more. I heard her stop, then I heard her get out of bed quietly and she leaned over and said, "Greg, can I help you please?" Help me? How I wondered, but she showed me. She drew the sheet down and took my hard on in her hand. Then she leaned over farther and began licking the head of my cock. She was good. She licked slowly up and down both sides and then sucked my balls into her mouth and rolled them around. Releasing them from her mouth she held them in her hand and began fucking my cock with her mouth, up and down. Then she jerked it with both hands while sucking on the head. Finally it was too much and I shot my seed into her sweet mouth. She drank it all.

When I let loose with my cum I automatically reached over and tried to feel her pussy. I wanted to finger fuck her as she sucked me. Damn. I found out why she had never changed in front of me. She had a cock. A big cock. One bigger than mine. Fuck. What now. That had been a great blow job. I wanted more. I did not want this set up to end. But a cock! I wondered why I had stayed hard after I shot my cum. I must have been turned on. Hell. I liked trannys!

"Now you know Greg. Do you hate me? Do you think I am a freak? Do you want to move out?" She was in tears. She was wiping my cum from her mouth and wiping her eyes at the same time. Oh hell. She was still Kathy. She was still the girl I had grown really fond of.

"We can work this out Kathy. No problem, really. I have seen plenty of trannys on my computer. Maybe not in real life but you aren't a freak. There are thousands of trannys out there. O hell, let's just sleep on it and talk about it tomorrow."

So we did, or tried to. I am not sure either of us slept much, but I do know I was awakened by Kathy closing the front door on her way out to class. I was late myself but I could care less right now. I was in a dilemma. I liked Kathy and I had loved the blow job she gave me last night. It was the best I had ever had, and I'd had a few. This did not take a genius. I liked her. I liked what she did to me. I was staying.

That evening we went out for dinner. It was a Friday night. No school tomorrow for either of us. It felt like a date, with me out with a little pixie of an adorable girl. I saw envious stares from some of the single guys and even some with dates of their own. I was proud to be seen with my Kathy!

When we got back to the apartment something was definitely different. The most immediate difference was that when we went into the bedroom to change to more comfortable sleeping gear Kathy did not seem to mind changing in front of me anymore. We both removed our outdoor clothing for sleepwear. In the process we both got naked. I had a hard on. So did Kathy! Hers was bigger than mine. And I was wondering if it was her tits or her cock that was making me hard. After all I loved that tranny porn. And loved to see the hard cocks being used in them.

"Kathy, do you mind if I just touch your cock? I mean, I know it sounds odd. But you did give me a blow job last night. I just want to see what it's like. Okay? Do you mind. I have never seen a girl with a cock in real life. I would like to see if it is like mine. Okay?"

A blush passed over her face and a shy smile appeared. "No, it's okay. Really. Okay, touch it Greg. It's okay, really."

I was sort of tentative. I had never touched another guy's stuff. I had touched Kathy last night but that had been more of a surprise than a touch to really feel. I slowly walked over. Kathy was hard. I was hard. I touched her cock, then I moved my hand up and down. She moved into my hand and almost starting fucking it. I dropped it.

"It feels just like mine. Only bigger. Damn Kathy, your cock is bigger than mine."

She laughed and then she started jacking it off. I don't know why this surprised me. But she kept doing that to me, surprising me. She was feeling up one tit while she jerked off her cock. A look of ecstasy passed over her face and then she looked up and said, "Jerk yours too Greg. Please let's do this together. It can't hurt anyone. Jack off with me, please? I have never done this before. It feels so good Greg, please, jerk off with me."

Fuck it. I was hard. I wanted to cum. Why the fuck not. It wouldn't hurt anyone, she was right. Kathy was right. So I started jacking my cock off. I watched her cock and she watched mine. We were synchronized. Jerking at the same time, and getting faster and faster. O god, I could not hold off much longer. She shot her cum first and it went about 5 feet in the air. I shot just after her. But I hit her. I got my cum on her tits and she rubbed it in. Then she licked her hand. We both went to bed happy that night.

We had an unusual arrangement now. Either one of us could be jerking off at any time in the apartment. It was no big deal for me to walk in on her rubbing one out or for me to just walk over to the computer and bring up some porn and jack off. In fact, she would sometimes come over and finish the jerk off for me and then suck my cock for the cum. This was all giving me ideas that had never really occurred to me before. Oh, I had often imagined what it would be like to suck cock, but only when I was watching porn. Not in real life.

Finally, one night we were both naked, as we often were in our room now, and I was watching some tranny porn and Kathy came over. She watched with me and watched me jerking my cock. Then she did something she must have dreamed of often in the past few weeks. Her cock was as hard as mine. She leaned over and kissed me and I kissed her back. She was a beautiful girl. It was good. But then she put her hand on the back of my head and pushed her cock into my mouth. I say into, because I just automatically opened it to take her cock. I must have wanted this deep inside for some time.

I was not that good at it. This was my first time. But she guided me into doing it well enough to make her cum in about 5 minutes. I tasted cum for the first time. Hers tasted like flowers. I swallowed it and she kissed me again. I think that was when I truly began to love Kathy.

From that point on we often sucked each other off. Sometimes we would even 69. It was always good for her and for me too.

We would have to move on to something else soon.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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Posted 04 Jan 2014 10:51
I really enjoyed your story.
Posted 14 Dec 2013 20:37
I love this story. I hope you write more.

Posted 22 Nov 2013 18:32
My first Trans story, I liked it. It did however end too quickly, so that sucks. I liked it otherwise.
Posted 22 May 2013 12:43
Fantastic story

Posted 12 May 2013 20:18
Ended too abruptly
Posted 09 May 2013 10:40
great story very sexy, got me very hard
Posted 07 May 2013 14:10
Posted 18 Apr 2013 13:30
Good story! I think all guys think about Tranny's and have fantasys..Thank you for sharing!
Posted 05 Apr 2013 03:17
hey I liked your story, I really did, it was solid, I mean the details of activity you provided, the detail about the relationship these characters were developing was just great. The description of the setting was so complete. I reall felt this was a real place you know. You really built up the tension for the "surprise", though I would have like more description of how her cock felt in his inexperienced mouth and, what her cum tased like, etc... maybe a little bit more detail in that scene, i dont know. the accidental discovery things is of course good, oh I already said that. I hope this is useful feedback that is not ire inducing.

be well

Posted 23 Mar 2013 07:31
That was a very good beginning to thsi series. "V=5+++."
Posted 18 Mar 2013 20:20
Don't normally read this type of lit,Encountered two surprises, Kathy is a trany.. I enjoyed the story. Well written, nicely developed story line,& now Ill read the rest of the story... (-:
Posted 17 Mar 2013 14:27
Great surprise, loved the story keep it up.

Posted 16 Mar 2013 10:44
Great story and it was so sexy. Nice job. . .didn't know you wrote like this. You're awesome.

Posted 16 Mar 2013 09:11
this is well written and has a good story to it that flows smoothly
Posted 16 Mar 2013 06:59
Posted 09 Mar 2013 09:03
Love the story need a follow up now.
Posted 15 Feb 2013 23:04
Why wasn't that me at uni. Great story writting. Keep my little gurl clitty hard all the way through. xxoo
Posted 07 Feb 2013 15:05
good story and fulfilling - hopefully you will write more

Posted 05 Feb 2013 14:50
Great story! Love to hear more.
Posted 05 Feb 2013 11:11
This is good but you should keep on with the story!

Posted 04 Feb 2013 19:45
An excellent story, very well done!
Posted 03 Feb 2013 16:00
Well written story and something I'm sure a lot of us in the same situation would have done. I like that the story was written in sort of a real world situation. Looking forward to reading more.
Posted 03 Feb 2013 14:54
Very nicely written, hope you share what they move onto with us.
Posted 03 Feb 2013 02:30
Wow I loved this story and feel so envious of your experience, I hope there is more to come from this situation.
Posted 02 Feb 2013 23:10
very nice ,i wish i could meet a tranny like kathy
Posted 02 Feb 2013 22:43
Awesome story got me so turned on
Posted 02 Feb 2013 21:52
Good story.....surprise
Posted 02 Feb 2013 05:08
great jerk off story

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