sexstories.com


Introduction:

A pilgrims progress
Bob walked down 8th Ave. and turned onto 43rd St. after a half block he reached his target. He wasn’t sure if he liked this assignment or not. His editor at the newspaper where he worked had asked him for a 1000 words on alternate lifestyles. In fact newspaper was kind of stretch, it was a weekly and not much more than a shoppers guide, one cut above the ‘Penny Saver’ types. But when your degree in journalism is from Altered State U. (Alfred State) you can’t be that choosey. So here he was in Manhattan about to visit and try to interview the denizens of a drag bar.

It was only four in the afternoon, so he was not going to get many patrons to interview. These places in Manhattan don’t get going until after 10 PM and aren’t in full swing until 1 in the morning. His editor had given him a train pass and $50 bucks to cover expenses, which would not last all that long.

Stepping into the cool of the bar, he was assaulted by the usual bar smell of old beer, whiskey with a hint of urine and a touch of vomit. It was almost frigid in the bar after the hot August sun. The owner had the ac running full blast, because he knew when the full crowd of drag queens, she-males, transsexuals and their admirers filled the joint, the temperature would go through the ceiling.

After a moment to allow his eyes to adjust to the interior, Bob looked around to find a place to sit. This place made him nervous, as did the whole assignment and he wanted to get it over with as quickly as possible. Looking around the room he saw a fat bald guy sitting with two girls at the bar, and one lone woman about half way down the bar. The fat bald guy turned out to be the bartender, who lumbered to his feet, came around the bar and placed a napkin on the bar about one seat down from the lone woman. Bob realized this was his designated seat.

Bob ordered a glass of beer, figuring to make his money last as long as possible, and was amazed to find a draft beer was five dollars. He took a sip and looked around the bar again, when he got to the woman seated next to him, she smiled and stuck her tongue out at him. Not in the manner of children, but full out and down her chin. ‘That is strange.’ He thought. Had he bothered to read up a bit on his subject, he would have realized that the tongue was an invitation, a come on.

“Hi.” Said Bob.

“Hi yourself.” Replied the woman. She was small breasted, with long dark hair that hung almost to her waist, pale skin that appeared almost translucent. No sun worshipper here. “Scoot over a seat so we don’t have to shout.”

Bob moved over. After and awkward pause he began to explain his mission, as rapidly as he could words spilling out. “Maybe you could introduce me to one the people here so I could get my interview?”

“Why not me?” asked the woman, “I’m a transsexual or she male, aren’t I good enough for you?”
“Oh, I just thought you were, well you know.” Came a tortured reply, as Bob blushed.

“Well good, I am supposed to pass. Good thing I told you now, before I was six inches up your ass don’t you think.”

“Huh.”

“Just kidding, I am Fran, or Frannie, and you are?”

“ Bob” he blurted out.

“Well Bob, let me fill you in. I am 26, and have been living as a woman since I was fifteen. I had my first encounter with a man when I was 13 and discovered my homosexual nature. That didn’t quite describe it though. I was an effete little boy, undersized and not interested in sports. So determining that I wanted to live and act like a woman was just a logical choice. Luckily I react well to hormones so no need for breast implants. Have had facial surgery, nose, cheekbones and voice box. Plus some work on my hips to make them womanlier. My equipment still works, wanna see it.”

“Ahh, no. Wow, that’s what I wanted to hear.” Said a delighted Bob. “How did you know, you know?”

“It came over me a little at a time, I knew I was gay, but doing the drag bit seemed to make it alright. Lots of straight men will go with a she-male, that would have fits if approached by a twink.” Came the reply from Frannie. “When I was 13 was seduced by one of my teachers. He kept me after school one day and had me suck his cock, it seemed the most natural thing in the world to take his cock in my mouth. Then he bent me over his desk and fucked me. I was in heaven, he chickened out though. Where I lived, in an Irish neighborhood, he would have been lynched if he had gotten caught.”

“Besides that what do you do now?"

“Oh I am a computer coder. Went to Junior college as a girl, and got a programming degree. The alternative isn’t very nice and that is porn or hooking. That doesn’t appeal to me guess there is a bit of the Irish training still hanging on in me. So I come in here, but am careful. Lots of straight guys will be in later on, some want a blow job, others want to blow a queen, and some come to get their shit pushed in, takes all kinds you know. One thing you should realize is there is a bit of sadism and masochism in all homosexual relationships, perhaps a little less with she-males, and trannies though. Guess you could say that is why we like to change our appearance so we get more loving with our fucking.”

Bob was furiously taking notes on his little pad. “Do you ever have someone, you know try and black mail you?”

“No, because anyone that knows what my real equipment is, has either had it in his mouth or up his ass, and wouldn’t dare say anything for fear of exposure himself.”

“Well you are telling me.”

“Yes Bob, I am, but the night is still young, and you’re so beautiful.”

“Ahhh, I don’t, well you know.”

“Just a little joke there Bob honey. To use a football analogy, right now you are a ‘tight end’ spend some time with me and I will turn you into a ‘wide receiver.’” Frannie grinned.

“I guess the next logical question is: Are you happy?” Asked Bob.

“Content and accepting would be the more correct way of stating it. Have spent a lot of time in therapy asking why me? Finally decided to accept what I am and make the best of it. You know, find a good man, settle down and have a few kids. Adopted of course.”

“Well by way of thanks let me buy you a drink.” Said Bob.

“Okay, but let me order, hey Cliff, two orgasms.” Frannie shouted to the bartender.

The bartender mixed to shooters that looked exactly like a load of cum floating in the brown liquor.

“Okay Bob baby, down the hatch.” Grinned Frannie as she drained her shooter then licked her lips.

The bartender relieved Bob of a twenty for the two drinks.

Bob downed his obscene looking concoctions as Frannie had. It tasted much better than it looked, being a gooey blend of several different sweet creamy liquors. The warm liquor hit his stomach hard, and caused an immediate buzz.

“This place is expensive Bob, I saw you wince on the price of those drinks, but that is what you get for coming in a place like this. Now, my apartment is just a couple of blocks from here, why don’t you come over for a drink, and, we can continue the interview there.”

“Okay.” Said Bob, relieved that he wouldn’t have to blow his entire expenses on another round of drinks.

The apartment was more like 8 blocks, over an avenue and up to 48th St. It was a 10 story brick building with a court yard, and quite well kept. No athlete, Bob was breathing hard and sweating by the time they arrived.

Frannie’s apartment was on the fourth floor, and was quite impressive. There was a sofa in the living room facing a large screen TV, a combination kitchen dining area and a couple of doors which Bob assumed were the bath and bedroom.

“Gee, this is very nice, much better than my place up state.” Said Bob.

“Well your just starting out aren’t you Bob baby, you will get there. Have a seat on the couch, I call it the Mayflower.”

“You named your couch the Mayflower, why is that?” Asked a puzzled Bob.

“Because dear sweet Bob, many a little pilgrim has come across on it for me.”

“Sorry I don’t get that one.”

“Oh you will get it don’t worry Bobbie dear. By the way do you have a wife or girlfriend upstate?”

“A girl friend. We talk about getting married, but I don’t know, my career isn’t exactly taking off.”

“Is she a good fuck?”

“I, I, don’t know what you mean.”

“I mean Bob, does she put out for you. If she doesn’t fuck, at the least does she give good head, really suck your rocks dry?”

“Ah, well, we aren’t very good at, I kinda of well you know.”

“Oh Bob you make it sound so perfectly clear you ain’t getting any from her, maybe pussy isn’t what you really want. Here lets watch a tape, and I will get us a drink.” Going over to the VCR Frannie selected a tape, plugged it in and then went to the kitchen and fixed two White Russians.

Bob got out his note pad as the tape started. The girl in the tape was short with a long curly blond hair in the style of today. The guy was kind of fat and bald. They necked for a while. Then she kind of pushed the guy down to her crotch where in place of a cunt, was a large prick and balls. She was a she-male. The hero of the film began to eat her, first the cock, then the balls and finally her ass. Bob was fascinated, to this point he had no idea what or how any of this was all done. He became so fascinated that he didn’t realize he had consumed the entire drink Frannie had prepared for him.

The film continued and the ending was the guy mounting the she-males cock. The she-male fucked him and jerked him off, he finally spilling his seed all over her stomach as he bounced up and down on her cock.

“So Bob what did you think?”

“It ahhh, cleared up a few points for me.” Said Bob, whose throat was kind of constricted at this point.

“Let me get you another drink, and we can watch some more tapes.” Said Frannie as she took Bob’s empty glass for a refill.

Bob watched tapes for the next hour and a half. All kinds of acts and positions he could never have imagined, and it didn’t seem strange to him, since half the participants looked like girls.

Then he saw a particularly hot short. “Bob, you will like this one because the she-male is really good looking and likes to be fucked, plus they seem to like one another.”

Again his eyes were glued to the set, and Frannie had been correct. The she-male was active and enjoyed being fucked, and at the end as the guy jerked himself to a climax, she ate him with obvious delight as he came in her mouth.

“Pretty heavy stuff aye Bob?”

“Yes.” Replied a somewhat shaken Bob.

Frannie leaned over and kissed him. He was shocked at first but responded, her face was soft and smooth as she explored his mouth with her tongue. Then her hand went into his lap and began to message his cock and balls, as they continued to kiss. They kissed and necked for about fifteen minutes. One handed she reached up and pushed the top of her dress down revealing her breasts. Then she pulled up her dress took Bob’s hand and placed it in her crotch and held it against her cock and balls. Breaking the kiss, she bit his neck softly then whispered in his ear: “Just pretend you playing with yourself Bob, don’t think about it.” Meanwhile she pulled his cock out of his trousers and caressed it and his balls. His girlfriend never played with him like this.

Bob was amazed at how hard he gotten, and how nice Frannie’s package felt in his hand as he explored the area. They continued kissing and sucking each other’s tongues while their hands continued the mutual masturbation. Frannie broke the kiss and leaned down into Bob’s lap and took him in her mouth. Bob was shocked by the sensation and started to quiver. She only licked him a couple of times when his body went ridged and he shot into her mouth. Frannie sucked him dry, sat back up and grinned at Bob and kissed him deep and hard.

After another fifteen or so minutes of this heavy petting Frannie leaned back and with her right hand she held her cock in the air and with her left she gently guided Bob’s head onto the waiting member. “Please Bobbie, eat me raw, suck me off.” She slipped her cock into his mouth and he was powerless to resist the action. “Oh Bobbie honey that is good, kiss it lick it, suck my balls.” The cock end was covered with pre fuck lubricant as Bob slobbered over the head, finally having decided to copy what he had seen in the videos. For the next twenty minutes Bob copied every thing he had seen on the videos, as he explored Frannie with his mouth. He sucked her dick, her balls, then licked her asshole as she wiggled and cooed encouragement to him. His hand stole into his own crotch and found the unique pleasure of playing with his prick as he ate Frannie’s cock and balls.


Finally Frannie felt herself ready to catch a nut: “Oh Bobbie, that is so good, eat me Bobbie, eat me.” Whispered Frannie as she began to fuck his mouth. “That’s really what you want isn’t it, now hold still Frannie’s going to cum in your mouth.” Frannie held Bob by the ears and with his head still shot her load deep into Bob’s mouth and like the she-male in the film he gobbled it down, he was happy.

“Bobbie that was so sweet of you, now I am going to fuck you, here take your trousers down, and I will make a woman of you.”

As if in a trance Bob undressed, as Frannie stretched out on the couch and jerked herself back to and erection, then with personal lubricant made her cock extra slippery.

“Just like in the video Bobbie, straddle me and sit on it.” It was rough on Bob, but Frannie was patient and finally had her cock worked up his ass. With a slow rhythm she fucked him playing with his cock at the same time. Bob’s guts were in turmoil over this first ever intrusion, but he got a raging hardon from the attention to his ass. It was about fifteen minutes before Frannie could cum again, but when she felt her nuts tighten she pulled Bob down on top of her and kissed him as she pounded out her orgasm up his ass. His cock shot as she came, pressed as it was between the two bodies as it was.

They lay in each other’s arms for a while, kissing and enjoying the after glow, glued together at their stomachs by Bob’s cum.

“You’re a perfect little girl, you came when I did. Oh Bobbie, you are sweet, how did you like your first real fuck?”

“I, don’t know, didn’t know I was gay.”

“Well, we live and learn don’t we. Hope I didn’t get your pregnant didn’t wear a condom.”

“That can’t happen can it?” Exclaimed an upset Bob.

“No silly, I was just making a joke for you. No go to the bathroom and get me a washcloth. Then I will teach you how to 69, you can’t tell whose cocks is whose.” So it went that evening, the two new lovers fell asleep with their heads in each others groin.

The next morning Frannie took Bob into the shower, then introduced him to an enema. Afterwards she taught him to play horsy. He was of course the mare and found he loved being ridden high, tight and hard. After that morning he looked forward to getting on his hands and knees and having his ashes hauled from behind.


Epilogue:
Bob gave up his apartment upstate and moved in with Frannie. He got a job on a New York Weekly writing political commentary. He has decided to remain a male, but behind closed doors Frannie uses him like a woman. Occasionally they will have a third over for fun and games. Bob has found he likes to have both his ass and mouth stuffed at the same time.
20 comments

anonymous readerReport

2013-01-26 18:25:47
I think this a great story!!! I have had 10, or 12 and really get along well with the nice ladies, in fact I like them better than women. I have never been with a man just shemales...all very passable have taken them out on dates now I want to meet one that's not a working girl. I want one to live and love, but she has to be passable. I love to top and bottom.......

Anonymous readerReport

2009-11-24 22:48:02
great story just wish it was me

kenbReport

2008-09-12 15:29:07
Great story!! I fantasize being fucked by a tranny.

READERReport

2008-03-09 10:42:14
i am a young male and i really want 2 get fucked and fuck a shemale i cant stop thinkin of havin a chicks dick in my ass and in my mouth, n e 1 interested?

READERReport

2008-02-21 02:11:06
Im a she-male and i find this story delightful

SUBMIT A COMMENT
You are not logged in.
Characters count: