Chapter 1 - Jessie and Wit

“You’re married aren’t you?” The clerk asked as she took my money.

“Why would you ask that?”

“Evading the question, yep married and for quite a while.” She said it with such a smile that I couldn’t help but respond.

“Yes, as a matter of fact I am.” Well, I know I wasn’t married anymore, but it was still so recent that I still felt married!

She grinned like a little schoolgirl. “I knew it! And from the stuff you’re buying, I bet she’s out of town.”

I shifted nervously without saying anything. She was more than out of town, unless Heaven counts as a town, but it wasn’t something I wanted to talk about.

She must have caught my mood swing. “Hey, it’s okay; I don’t mean anything by it. I just really like people and I’m always playing this sort of guessing game. I don’t really care what you buy, as long as I get to ring it up and get the commission.”

“You work on commission here?” I was grateful for the change of subject.

“I do, anyway. What I make depends strictly on sales. We rotate around a lot. The girls downstairs make a ton on clothing, but the movies are probably our biggest sellers.”

“I never thought you would actually work on commission.”

“Hey, are you in a rush?”

A little hesitantly I replied, “No.”

“Great. Look it’s really quiet this late in the day and I am due for my dinner break. If I don’t get one now, I might never get one. We have a bunch coming in for a party later. Why don’t you pop over that fast food place across the street and get me a number three, iced tea to drink and get your dinner. Come on back over here and we can eat together and talk for a bit.”

I walked out of there, not sure what the hell just happened to me and drove over to the hamburger joint and got her dinner, done twice, and actually went back. I felt like I was in a daze, hit by a cute little twentyish Mack Truck.

“Great! Come on and follow me, the break room isn’t being used for a while.”

Down the stairs I wondered what the hell I was doing. I make a quick stop into an upscale porno shop just north of town center, just to pick up a couple of movies and maybe a book or two. I really was surprised how nice the place was and how big. There were signs directing people to the fetish-wear sale in the basement, tons of DVD and Blue-Ray movies, and an incredible collection of toys. All I was going to do was grab a couple of movies, maybe a book and go home. I know, dull life, but I was still in some adjustment phase after my wife passed.

The next thing I know the clerk, a surprisingly innocent looking early twenty-something, starts talking to me and I am going down the stairs with her to eat dinner. She did sort of con me into buying, but that’s OK. Should I let my imagination run away with me? No way! She’s cute, probably a college student here. I am nearly twice her age, not in bad shape, but nothing a girl like her would be interested in. Maybe she’s in a psychology class and I just became an experiment. What the hell it’s better than eating a nuked-dinner alone at home!

Her nametag said ‘Jessie’. We sat down and just started talking like we were old friends. She was so easy to talk to attentive, honest in her comments, and very intelligent. She talked about college ... I was right a student, at least part of the time ... and I talked about my family, she even got me to open up about my wife. She was empathetic without pity. Jessie was wise beyond her years and for the first time, I didn’t mind talking about everything. We finished our burgers and then she hit me right between the eyes.

“Have you ever met one?”

“Uh, one what?”

“A TG.”

“A what?”

“A Transgender, just the like in the movies you just bought. Have you ever met a real transgendered girl before?”

“I don’t know.”

“You mean you can’t tell?”

“Well, I’ve seen cross-dressers and some drag queens, but I think a real TG would look just like a girl. Isn’t that the idea?”

“You wouldn’t believe all the types we get in here. Some of the TG’s are still so close to being guys they are so nervous and yet so sweet. They are more open coming here to buy stuff rather than the mall. That’s why we stock such a large clothing area. Don’t get me started on drag queens; they are so flamboyant that they are a riot and so much fun. So, you have never met one?”

“Not that I know of.”

“So why this fascination?”

“I don’t know if I would call it a fascination. I was looking at your movies and saw the cover. It looked really interesting and something completely different.”

“Look, don’t take this wrong, but you just didn’t strike me as the type.”

“Type?”

“Well, you come in and wander all through the movie section. You caught my eye when you kept stopping at that one spot, where I know we have some of our raunchiest TG videos.”

I think my face turned a bright red, because she reached out her hand and touched mine.

“Don’t sweat it. I’m not condemning you. I just found it very interesting. Sexuality should be expressed rather than repressed. The vids, books, toys, and even clothing can help bring that out. I love all of it.”

Her hand was warm and very tender. I wasn’t sure how to respond.

“Look at it from my point of view. A handsome gentleman comes in. Right away I and the other clerks saw you. We talk quite a bit about our customers, amongst ourselves only -- where will they go and what will they buy. It’s just a way to pass the time. Like most guys you head to the movies. Women usually head to the toys, and lots of folks head to our dungeon.”

“Dungeon?”

“Oh not a real one, that’s what we call the basement. We expanded last year into clothing and specialty items. They are down here in the basement. We used half our storage space the just the leatherwear. It’s really cool. Maybe I’ll take you on a tour later. Oh no, that party.”

“You mentioned the party before? What’s going on?”

“We have a bunch of ladies coming in for a bachelorette party. When we know they are planning to get real wild, we use part of our basement to give them some serious privacy. They can get as crazy as they like. We cater it, provide costumes, toys, entertainment, and whatever else they want. It makes a cool profit for us and we can usually have some fun too.”

I didn’t realize how big this place really was. I just assumed movies and books. Jessie was so matter-of-fact about it all. I think that helped me relax.

“Suzie, the little girl who was at the counter, figured you for a romantic, erotic movie to spice things up with your wife. Ronnie, the tall sexy blond, thought you looked too nice to be that romantic, so she guessed something really slutty. Angie was busy with another customer so I don’t know what she thought. I was real surprised when you kept going back to the transgender stuff and it got my curiosity up.”

“So what was your guess?”

“Oh I’ll never tell you.”

I sat there thinking about it. Getting those movies was a spur of the moment thing. I was probably going to find something nearer to her friend Ronnie’s idea than the other clerk, but those movies caught my eye.

“I would have gotten something more explicit, but the shemale ones just seemed to jump out at me. And back to your original question I haven’t met one that I know of.”

She said, “Would you like to?” in a real quiet voice.

I paused when her hand squeezed mine. I forgot she was even touching me.

“I am asking for real. Would you like to meet a real transgendered woman? She is very feminine, lives as a girl, and no one has a clue about what’s under her clothes unless she tells them. Would you like to meet her? Think about this before you answer because if you say no, or make a smartass crack the subject will be dropped.”

She was very serious. So in all seriousness, I thought about the answer. Did I want to meet a real TG? Jessie wasn’t offering sex or anything, just a meeting. What would it be like talking to a girl, knowing she was ‘different’? Would it seem normal to me, or would I freak out? To be honest, I wasn’t sure.

“Jessie, I don’t really know. I’m not sure I would be able to talk with her. I mean I have no experience, I would hate to say something wrong and hurt her feelings.”

She looked at me for a long minute. “Wow that was an honest answer. Some of the guys we get in here would jump so hard at the chance that it would be scary. Others get insulted and put on an ugly front, I hate that. You really thought about it and you aren’t sure.”

She stood up and gathered our trash. “Come with me.”

She held out her hand. I took it and she led me down past a couple of storerooms to another break room, this one smaller, more intimate. It had a couch, a couple of chairs and small tables, and a few nice art pieces and mirrors on the wall.

“The other room was going to be used as a dressing room in a few minutes; that party I told you about. I didn’t think you would want to be there.”

“Thanks that might be a little much.”

She sat me down on the couch and them to my surprise, she sat next to me. My arm went around her and she burrowed her face into my chest, it was a moment before we started talking again.

“You are the real deal, a thoughtful guy who isn’t afraid to be honest. From what you told me about your wife, you are also lonely and your kids are all grown and gone. Look, I’m not offering some sort of super sexual weekend; I was curious if you wanted to meet a TG in person. To talk and explore yourself little bit. Who knows what might happen. I wasn’t looking to set you up with someone looking for a sugar daddy.”

“Jessie, I wasn’t thinking that. I really don’t know how I feel. I saw the movies, they were intriguing. I’ve never given the idea much thought. I know I am not gay, but it was so different.”

“So dirty?” She said looking at me with a strange look on her face.

“No, not dirty. Maybe some scenes in the movie might be, but I was really curious, nothing more. I didn’t come in here looking for a TG, or even a TG movie. I’m not sure how I would feel meeting one. Hell I’m not sure how I would talk to one.”

“You talk to one just like you are talking to a girl. I mean she is a girl, isn’t she?”

“Yes, she would be. I guess I’m not making myself clear. You really hit me with this out of the blue. Look, she must be a friend of yours?”

“You can say that.”

“Then what do you think I should do?”

She twisted around and knelt on the couch next to me, looking at me. “You don’t even know me, how can you ask me that?”

“You have pretty good head on your shoulders and so far you haven’t done anything to make me think you would have me do anything bad. What do you think I should do?”

She took my hand again, and then opened my palm. She slipped my hand under her skirt and I was holding testicles, just like that. She held me tight so I would have a knee jerk reaction. Jessie was/is a transgendered and for the first time in my life I was holding a set of balls that weren’t my own. I was totally shocked. I tried to speak, but she placed a finger over my mouth.

“Shhhhhh, just go with your feelings.”

I held her sac in the palm of my hands and curled my fingers around it until it rested comfortably. She let go of my wrist and in an amazing feat of dexterity curled back up against me with my hand never leaving her balls.

No words, nothing at all but me holding a lovely young woman in my arms with my hand under her skirt. If anyone walked in they might raise an eyebrow, but they wouldn’t have a clue.

I held her sac very carefully, letting its weight rest in my hand. Then I gently applied a little pressure, just like I do when I am masturbating, or my wife did when we are fooling around. Jessie inhaled sharply. She was very responsive.

I gently kneaded her balls, feeling them through the material of her panties. They felt warm and heavy. I was starting to get turned on. Across the room was a small mirror and I could see Jessie clearly, her eyes were closed and her tongue would come out and quickly lick her lips. She was the picture of excited femininity. I could see my hand under her skirt and see my movements through the material of her skirt. Her hair smelled nice, something I couldn’t place, but most of my attention was on the mirror. It was such a sexy picture and knowing what I now knew, there was an element of mystery that anyone who could see us there wouldn’t have a clue.

The door burst open and two girls carrying a bunch of stuff burst in and then quickly backed out muttering apologies.

“Damn, I forgot to lock the door.”

Jessie got up and my hand felt cold all of a sudden. She locked the door, paused and turned to look at me.

“No one will interrupt us now, unless I tell them to. I have the only key to this room. The question is do you want to continue, or do you want to leave?”

I thought again, hard! I should leave. I know I was excited, Jessie would see it if she looked down. Her face had an earnestness to it. She didn’t want me to leave. At the same time the spell she had weaved was broken and I am not sure we can get it back.

“I would rather stay but I do have one wish”

“Only one?” She said with a small smile.

“Take off the panties, please?”

She looked surprised. “Anyone else would have wanted me naked by now. You just want to feel me without the panties?”

“I’m still not sure what I want, but before the evil twins there broke the spell, I was thinking about what you would feel like without the cotton panties.”

“Suzi was right, you are a romantic. You want to go slowly and relish the feelings as much as I do. You have no idea how happy you made me when you didn’t fly off the handle.”

She turned away from me and reached under her skirt. I got a glimpse of the most perfect and feminine rear-end I have ever seen as her white cotton panties went down her legs. She had a pair of great legs! She bent at the waist and kept her legs straight. As sexy a pose as I had ever seen.

She came back and slipped against me again, this time her back was pressed toward me, but it gave me better access to her legs. I ran my hand over her thighs and she sighed. Then, unable to prolong it any longer, I felt her testicles again; this time I could feel her warm skin. There was a third thing hanging there that surprised me, but it shouldn’t have. Without her panties to hold it in position, her cock hung down with her balls and it all made a nice package in my hand. Rolling them and teasing them lightly made her penis jump a little. She was getting excited! I still couldn’t see anything because of her skirt, but when I tried to lift it up, her hands smoothed it down.

In the mirror she was smiling at me. I smiled back and then she took my hand and made me squeeze her harder. I thought I might hurt her, but her penis definitely liked the firmer attention. A minute later I was holding an erect penis, and I was jerking it off like it was mine. Jessie must have liked it because her ass was pressing into my hip with every move. My own cock was straining at my Dockers and a small precum stain bled through the khaki material.

Jess finally spoke. “Would you like to see?”

“Yes, Jess, very much!” I gasped out.