Conversations With Jessie free porn video

"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 OK; 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 north of the city, 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 about 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.

She looked at my face in the mirror and took the hem of her skirt in her hands. I could see the tip of her penis pushing at the material of her skirt. She waited, building my suspense until I wanted to scream at her to let me see.

She flipped the material up and I got my first real look at her penis, her cock. It was beautiful! My hand was squeezing the base, just like I love when my wife did it to me. The blood had filled it and its head was a dark red-wine color. There was moisture on the tip. Stroking up and down it felt even better than it looked. Each time I pulled down, Jessie would push her ass against me in such a sexy way.

I think she was close to cumming! I grabbed her hair and pulled her face around to mine, somewhat forcibly. She fought for a second, until I kissed her.

I was kissing the hell out of a a TG . . . . no, I was kissing Jessie . . . and I loved it! She turned, my hand felt so empty, but then she pressed against me, almost laying on me and she kissed me back; our hot, stiff tongues fighting each other. Her body was so vibrant against me, her cock pressing against mine as I parted my legs to let her in closer. Before I could get my breath back, she got up and pulled me forcibly to one of the chairs. She sat down and pushed me to my knees.

I looked at her cock from only an inch away. The veins were standing out; there was a dark seam along the bottom. My hand held her testicles again and my other hand grasped the base of her shaft.

I looked up at her and she still had that angelic smile that told me all was right with the world. Without any prompting, I tasted her cock and licked the very tip lightly. It felt hot and tasted somewhat sweet. I ticked her glans, and was rewarded with a sigh. Stroking her cock at the same time I was fascinated by how the head would expand and contact. I popped the head in my mouth and I could feel it as it changed. Jessie was moving now, pushing against me. She was fucking my face, it was great. When she pushed forward, I sucked her completely in my mouth. When she pulled out I tighten my lips as tight as I could. She grabbed my hair and started getting frantic. Suddenly, with a huge scream, the first jet of her cum caused me to choke a little. I swallowed the bitter stuff as best I could, but here was so much, I could feel it dripping down my chin.

When she fell back, her cock had softened, and there was cum on it. I stared at it, unable to believe what had happened. I don't know if it would ever happen again, so I placed my head back in her lap and licked the rest of her come from her cock.

"Knock, knock."

Jess stirred. "What is it?"

"Miss Jessie, we have a problem upstairs, Ronnie really needs you."

"Just a sec."

"Honey, I gotta run for a few. Suzi is a good girl and a good friend. She'll help you get cleaned up." She pointed down and I could see the mess I made when I came. I didn't even realize I had. "It's OK, baby, just don't leave until we can talk. This may take a little while."

She kissed me and stood up. A few brushes of her hands down her skirt and, other than her tight nipples, she looked like an angel again.

When she opened the door, a pretty little Asian girl peeked in. "I am so sorry, but it is important."

"Fine, I'm going already. Look, Suz, would you help my friend get presentable again. I'll be back in a few."

Suzy came in and I struggled to my feet, still dazed.

"She's pretty amazing, isn't she?"

"That she is."

Suzi caught some of Jess' cum from my cheek with her finger and licked it off. "Delicious too!"

We both laughed and any feeling of embarrassment at my predicament evaporated against Suzi's laughter.

"Let me get you a couple of wet cloths and a towel. Go look at yourself in the mirror. You have that 'just fucked' look that I love in a man."

I looked like a wreck. My hair was matted, my shirt wrinkled and cumstained. My tan Dockers look like I pissed in them because the cumstain was huge. I also had a smile that refused to go away.

Suzi came back in, all business. "We aren't a department store, so you'll have to make do. Get undressed."

Her no nonsense attitude got through, but her hands with those two warm and wet cloths wasn't business-like. She cleaned me in places only my doctor ever touched before. It was getting to her as well. "I gotta stop this, Miss Jess will kill me."

I grabbed her hands. "I can't have your blood on my conscience." I took the towel and dried myself off in the mirror, Suzi sat on the couch behind me.

"How old are you?"

I told her.

"Wow that's the same age as my dad, but if he was in as good a shape as you, I would be in a ton of trouble with my mom." She smiled her exact meaning. Suzi also had her own hand up her skirt. "I heard Miss Jessie cumming while I was outside the door. I've never heard her scream like that, not even with me!"

I felt a weird kind of pride at that, but soon my attention was on Suzi. Her skirt rode up and she had no panties on. She was rubbing up and down and several not very father-like things popped in my head.

"Oh fuck, Daddy. Please Daddy, eat me, I need to come!"

Her eyes were closed, but her voice got to me and my dragging peter jumped up.

She looked right at me and opened her legs wide. "Make your little girl scream, Daddy."

That was too much for me and once again I was on my knees. My hands holding her legs wide open and my mouth feasting one a delicious wet and hair-free pie. Suzi was a wild one; she was pushing herself against me with complete abandon.

"Ahhhheemmmmm!"

Suzi jumped up. "Oh shit, Miss Jess, I'm sorry I couldn't . . ."

"Oh pipe down you little slut. I was expecting more self-control from you." Her eyes frozen against me.

When I tried to get up, she pushed me back down. "You might as well finish what you started. This fucking slut will be bitchy the rest of the night if you don't finish."

Suzi cried out in glee and pulled my head back down. For a few moments I wasn't into it. I felt like I had betrayed someone, but Suzi tasted so damn good I got back into things and soon had her back on the edge of the couch fucking her pussy against my face.

Jess got behind me and started paying with my balls and my ass. She leaned her body against me and was whispering in my ear.

"Tongue fuck the little slut, she loves it."

She was heavy against me, but so damn sexy. She was kneeling there and soon I felt her cock pressing. Jess was getting excited! She licked down my back and started tonguing me; she spread my ass cheeks and started licking my asshole. I was scared and excited, finally Suzi screamed into another world and came hard.

When she got up, Jess was once again at my ear. My asshole was wet and her cock was pushing against me. I knew what she wanted, but I wasn't sure about it.

"Get out slut, I'll deal with you later. In a few minutes send Ronnie down."

Suzi scampered to obey and Jess pushed me against the couch.

" I imagine you know what I want to do. Have you ever had anything in your ass?"

"No." I replied nervously.

"Hey, hey, I'm not mad at you. I just have to keep Suzi in line or she would fuck anyone who walked in. She really is a sexy little slut. I am not surprised you went down on her. Hell, I would have been more surprised if I came down here and found you dressed.

I breathed a sigh of relief, and then she touched my asshole again."

"I really want this; the question is will you give it to me?"

She pressed against me and I felt her bare chest. She had heavy breasts and she ran them up and down my back. Her cock was free and it pushed against mine and my balls.

She got up and pulled me over to a chair. "Here, now you can see us in the mirror."

She lay back against me and the sight of her sexy female body against my back got to me. She pulled back and forth on her knees, pushed her cock, teasing the tip along my balls, then laid back on me and pushed those breasts along my back. Three times and soon I was rock hard again. Her finger touched my asshole and she pushed in the tip of her finger.

"You have such a tight little pussy, honey."

The door opened, but I didn't see who came in. I was watching Jess in the mirror mime at fucking me. It was so hot.

A tall blond climbed into the chair. She was naked, slim, nice chest, and another fully shaved pussy. She pushed me away from the edge of the chair, opened her legs and without a sound pulled me to her pussy.

"Eat her as well, honey. You were so hot eating Suzi that I thought you would like a taste of Ronnie as well. While you eat her I am going to take your cherry."

I was nervous, but I was also putty in her hands. She pulled out of the mirror view for a moment and when she came back she had something in her hand. Some type of lotion. She put some on her hand and then she touched me. It was freezing!

I yelled into Ronnie's cunt, but that only made her pull harder. She lifted one of her legs and while it got me a great mouthful of cunt, I couldn't see the mirror anymore.

Jess's hands massaged my ass and balls. The lotion was a lubricant obviously. She pushed one finger in and slowly fucked me with it.

"Oh damn, you have a tight pussy, honey. I can't wait to fuck you!"

Her voice was in my ear again, but Ronnie was bucking nicely. Then she turned over and opened her own ass cheeks. I heard her voice for the first time. Very low pitched and very sexy. "Eat my ass, bitch."

Jess's hand slapped Ronnie across the ass. "Honey here is not a bitch. You are to be nice or I'll send you back upstairs with an itchy pussy and no relief."

"I'm sorry Miss Jess. I got carried away."

"Don't apologize to me, apologize to Honey."

"I'm sorry I am such a bitch, Honey. You have a great tongue and I need it real bad."

I wanted to tell her my name wasn't Honey, but Jess pushed me back to her ass and my tongue sunk in as far as it would go.

Ronnie yelled and pushed back, forcing me against Jess who was now rubbing my ass with two fingers. I was hard as steel every time her fingers found my prostate.

Ronnie went into light convulsions as Jess pressed something larger to my virgin ass. The head of her cock popped in and the pain was bad for a few seconds. It took my breath away.

She left it for a few moments and I got my head up to see the mirror. The distance was just enough that all I could see was something connecting her to me. When she slowly leaned forward the bar of iron in my ass felt like heated steel. She went all the way in and stayed there. The picture was incredible. She was pressed against me and I was supporting her whole weight. It felt like the only place I was holding her up was my asshole. It burned then cooled, then she moved and it burned again, but not as much.

By the time she pulled almost all the way out the burning sensation had stopped. The feeling of fullness remained and I squeezed my sphincter hard, she moaned.

"Oh Honey, you feel so fucking good. I can't believe how perfect you are."

She fucked me again with infinite slowness. Ronnie slipped off the chair and I was leaning on her for support. She pushed her ass against me and we were soon a sandwich and I was in the middle. My straining cock found her cunt. I couldn't move, but every motion of Jess’s instantly went through me and into Ronnie. Ronnie's hand found me and repositioned me. My well-lubricated cock pierced her asshole in one motion. Now we were fucking. Jess was moving harder and faster. In self-defense my movements mirrored hers and that meant I was fucking Ronnie as hard and as fast and she was fucking me.

I couldn't believe the sensation. My heart was beating a mile a minute and my cock was like a piston in and out of Ronnie's asshole. I closed my eyes and gave into it all. I don't know how long we went, but I couldn't stop myself from cumming. I filled Ronnie’s ass but I stayed hard. I couldn't believe it. Jessie in my ass was like the ultimate Viagra. I kept fucking Ronnie not caring if she had come yet or not. Jess was pounding me harder and harder. The mirror seemed to be rocking with us and I couldn't see much. I felt her tense up, like she did before my first taste of cum. I drove into Ronnie and heard her scream. Jessie came in my ass! She kept going until I think I passed out.

I woke up on the couch. Ronnie, Suzi, and Jessie were there. My head was in Jessie’s lap, Ronnie was looking worried and Suzi was cleaning me up.

"That was incredible Honey. I've never seen a guy do that, Little Death, Le Petite Morte."

"It never happened before to me."

Ronnie looked better. "Honey I couldn't believe it. You fucked me unconscious and when I came to, you were still fucking me! "

She turned and ran upstairs.

Suzi was smiling. “That was pretty impressive, Honey."

"My name isn't . . ."

Jessie stopped me. "Here you are my Honey. I hope you can live with that. You know your life has changed tonight?"

I looked at Jess. "It changed to moment you tucked my hand under your skirt.”

She smiled. "There is one last little detail."

Ronnie came in with a couple of things. She handed me a bracelet. It was in between masculine and feminine and it just said "Honey". I put in on, rather proudly when I realized Suzi and Ronnie also were wearing similar bracelets.

The next item was an envelope. In it was a shitload of money.

I was floored.

"Don't get angry. The mirrors have cameras and everything we did was seen by the bachelorette party in the other part of the basement. These are your tips. I think they all have a daddy fantasy."

"And when you went down on me “ Suzi added, " half of those girls went nuts. The other half went totally insane when Jess popped your cherry. Right now we have a room of 15 women who were frigging themselves out cold."

"No, Jess! This isn . . ."

She stopped me. "I know Honey. We could have let you walk out of here none the wiser. But we don't lie to our loved ones. You have a right to know it all, and we will live with the consequences. If you hate us, we will understand. There is only one copy of the video and here it is. You can destroy it if you want"

"Why the recording?"

"We do this and things don't always go well. Sometimes the file was the 'evidence' we needed to stop someone from getting all legal on us."

I thought about it. Jess asked, "What I loved about you from the first moment we met was your honesty. Please believe me that this is the only copy."

"Oh, I believe that. I am not sure I can destroy it."

She smiled. "You can leave it here in safekeeping. You can come back anytime you want to watch it, or whatever."

"Whatever?"

"Whatever! Honey, you are welcome here anytime for any reason. You are honest and sexy, and willing to explore. We can help you explore, if you wish, or you can just stop in and say hello. This isn't a whorehouse, and the money you received you earned, even though you didn't know it. You are a member of the family now."

I smiled, and then was surprised when my eyes teared up at one word: "Family!"