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Becoming John Collins' Mistress - Part Two

I'm invited to spend a day with one of John's hunky friends
The next day, everyone was a bit hung over. I needed to pick up my car, which I’d left at the bar the night before. Joe said it was on his way and he’d be glad to take me.

I borrowed a raincoat from John to wear over my skimpy outfit, then Joe and I headed out.

Joe was making eyes at me during the drive, and I decided it would be best to come clean.

“Joe, there’s something you should know about me,” I started.

Joe quickly said, “Hey, baby, there’s a lot I’d like to know about you.”

“Yeah, well, I’m not completely what I appear to be.”


“Meaning, biologically I’m not a female.”

Joe looked at me in disbelief.

“You mean you’re carrying something extra down below?”

“That’s right… ”

“Well hey,” said Joe. “That’s cool, not a problem I assure you. I’m one of the most open-minded guys you’ll ever meet.”

I was ecstatic at what I was hearing.

“Oh, Joe, I’m so glad. I really like you.”

“And I like you. And I think you’re really hot. Say, are you and John exclusive?”

“No… ”

“Great. Then why not come over to hang out at my place tomorrow? Though, of course, you can bring John along.”

“Actually, John is going to visit family tomorrow. But I’d love to hang out with you.”

“Great. Why not come by around noon and we’ll make a day of it?”

“Okay,” I replied. “Sounds like fun.”

And so it was agreed. We reached the bar and I got out to get my car.

“See you tomorrow,” I said.

“Looking forward to it,” said Joe. “See you then.”

He drove off, and I got in my car and headed back to John’s to sleep off all the partying.

The next day, I awoke about 9:00 a.m. and went downstairs to find John finishing his breakfast. We kissed and I sat on his lap. I told him I was heading to Joe’s.

“Joe’s a fun guy. Have a great time. But I’m running late.”

So saying, we kissed one more time, I got up off his lap, and we said goodbye for the day. John headed out.

I headed to the bathroom and took a nice bath.

Then, after applying some makeup, I got dressed. I put on some white lace panties, then some black sheer pantyhose. I grabbed some cut-off jeans and slipped into them. They were very tight and cut very high, exposing part of my butt. I then slipped into a lacy white bra, and over this, a pink halter top. Finally, I put on some high-heeled sandals and some loop earrings. I was ready to go.

Once in the car, I looked at the directions I’d googled and headed off.

After driving about forty minutes, I was definitely out “in the sticks”. Woods were everywhere. I loved the woods, how great was this?

I decided to slip off my jeans as I drove. I always loved to do this, it turned me on so to be so naughty.

After another ten minutes, I turned into the road where Joe lived. I continued down the road about a half a mile without seeing a house. Then, up on the left appeared a clearing. There was a mailbox with the number one, which was Joe’s address. There was a driveway and I pulled in.

The house was set back several hundred feet. It was a cabin actually, very quaint looking.

I slipped my cutoff jeans back on, got out of the car and went to the door. I knocked.

Soon the door opened. There was Joe, dressed in a tight tshirt, tight bathing trunks, and sandals.

“Hey, baby, aren’t you going to give me a hug?” I asked.

He opened his arms wide and we hugged. I moved his right arm down to my fanny. He squeezed it with his big strong hand and I leaned in to kiss him. We kissed deeply and I grabbed his ass. I started getting hard and I’m sure he felt it. I massaged my cock against him and said, “Mmm.”

“Come on in. Make yourself comfortable,” said Joe.

So I walked into the middle of the main room and slipped off my jeans and pantyhose, leaving me in just my panties, bra and top.

“Have you got anything to drink, baby?” I asked.

Joe disappeared into the kitchen and returned with a couple of screwdrivers. I grabbed my purse and pulled out a joint. We sat on the couch, smoking the joint and sipping the drinks.

I was starting to feel quite horny.

I got onto my knees on the sofa facing the wall and began massaging my cock through my panties against the back cushions, all the while smiling sweetly at Joe. Soon my cock throbbed and stuck out over the top of the panties.

Joe reached over and slipped his hand beneath my panties, caressing and massaging my ass. I was so turned on, with this big stud ogling me and rubbing my ass while I rubbed my cock against the couch.

“Oh, Joe, I want to suck your cock!” I exclaimed. I sat back down on the couch and removed my halter top. Then I helped Joe take off his swimming trunks. After he sat back down, I leaned over and started kissing and licking his cock and balls.

“Oh, Joe, I want you to fuck my face. Would you fuck my face, baby?”

“Why, it would be my pleasure,” said Joe.

So saying, Joe stood up so I could lie down on my back on the couch, with my head braced up by the two couch pillows. Then Joe straddled me and began rubbing his cock on my face. I licked his throbbing dick and sucked his balls. He stroked his cock against my cheeks, against my eyelids, and against my forehead. His precum on my face let me know how excited he was getting.

Soon, he started stroking his cock as I licked his balls. He started to moan.

Then, still stroking his cock, he aimed it at my now open mouth and shot a large, hot, salty load onto my tongue. I reached with my hand and scooped some of the cum onto my fingers and began to wipe it all over my face. There was still a huge amount of cum on my tongue and in my mouth, and I swallowed it all. Then I sucked Joe’s cock to get every last drop.

Now Joe laid down next to me on the couch. We faced each other and he massaged my ass as we kissed deeply.

“Joe, you were really great!” I exclaimed. I slipped off my panties now and he then stuck his middle finger up my ass and I stroked my erect cock against his leg. I came very quickly, then sat up and licked my jizz off his leg and swallowed it.

After a few minutes of cuddling, we sat up. “How does a burger and fries sound?” he asked. “That is, if you still have room to eat some more.”

We both laughed.

“Yes,” I said. “Actually, I’m famished.”

“Great. I’ll get the charcoal grill going in back. While it’s heating up, we can shower.”

Needless to say, the shower was great! I scrubbed Joe and he scrubbed me. Actually, “fondled” is more like it, but we did get each other clean.

Afterwards, I dried my hair, then I put on some makeup and dressed in some pink lace panties, matching bra and a pink halter top that ended at my belly button. I then slipped into some high strapped sandals and headed out to where Joe was cooking our lunch.

Since there were no nearby neighbors, I felt quite comfortable dressed as I was. (And truth be told, I’m quite the exhibitionist anyway, and so neighbors were not a real consideration for me one way or the other.)

The food finally cooked, we sat at the picnic table and dug in.

“So,” Joe began. “How long have you been crossdressing?”

“Oh gosh,” I answered. “a long time.”

“I’m curious. I hope you don’t mind my asking, but I’d love to hear how it all started.”

“I don’t mind. But do you really want me to bore you with this?”

“I won’t be bored. Humor me.”

Accordingly, I delved into my genesis as a crossdresser.

“The first inkling I had of wanting to be female was in a dream I once had. In the dream, I was a woman stripping on top of the bar in a men’s tavern. I gyrated around, and I noticed how mesmerized the men watching below were. It gave me such a wonderful feeling, they worshipped me, and I loved giving them pleasure. I felt so free and so sexy and so at home up there turning them on! And I had the sense that I would be protected and taken care of by one of these men who worshipped me. I would give men pleasure and be taken care of in return.”

“Needless to say, when I awoke from that dream my underpants were saturated with cum!”

“And whenever I used to look at Playboy magazines, I always found myself wanting to be one of these naked lovelies. Again, the sense I got was that these women were worshipped for their willing nudity and taken care of. All they had to do was be sexy and available.”

“Then there was my elderly neighbor, Mr. Goodman. After graduating from high school, I began going over to visit Mr. Goodman. He would have me in for a coke and chat. I had no real close friends, so I enjoyed going over to pass some time. And he was obviously quite lonely.”

“One day my Mom was chatting with Mr. Goodman and mentioned she was going away for the weekend with a new beau.”

“Mr. Goodman asked if she thought I would like to spend the weekend at his house so that neither of us got lonely. As I’ve said, I did not have a lot of close friends at the time. My conflicted sexual feelings made me isolated; I preferred not to share my tastes with anyone. My mother knew of my preferences and she did not discourage me. In fact, from time to time when she returned from a shopping trip she would bring me some clothes, like panties or a nighty, that fit me.”

“My mother, who liked to drink a lot and have a good time, believed everyone should be able to do their thing as long as nobody else got hurt. And she told me she had always wanted a daughter, and said I could dress up however I wanted.”

“So I was in the habit of wearing girls’ clothing around the house, though I didn’t dare venture out dressed like that, for fear that if someone found out, I would be ridiculed and would never hear the end of it.”

“Mom was concerned, however, that I did not have a girlfriend or boyfriend.”

“So, as she chatted with Mr. Goodman, she said that yes, she’d like it if I’d spend the weekend with him, but that she’d have to ask me.”

“And when she asked me, I said okay, it would be a good thing to give him some company. Though I didn’t say it, I was the one really starved for company. Plus lately I’d had these fantasies of being a naughty girl for Mr. Goodman. So what the hell, I thought.”

“Early Saturday afternoon, after Mom had left on her date, I headed over to Mr. Goodman’s. He liked having a glass of wine and offered me a glass. It seemed early in the day for someone to be drinking wine, but I accepted since no adult had ever offered me a drink before. I tasted it and didn’t like it. But he coaxed me on, saying, ‘It will make you feel real nice. Don’t you want to feel good?’”

“Then he got up and said, ‘I have something to show you which I think you’ll like. But you must promise me that everything – the wine, and what I’m going to show you – will be strictly between us.’”

“Curiosity was getting the better of me and so, after taking another sip of wine, I said, ‘I promise. Our secret.’”

“‘Good,’ said Mr. Goodman, ‘I’ll be right back. Try and drink more of that wine, it’ll make you feel good.’”

“So, while waiting for him to return, I took a few big gulps of the wine. He was right, it made me feel real giddy and a little dizzy, but I liked it and I liked doing something grown up.”

“Soon he returned with a photo album. He sat on the couch quite close to me and said, ‘I think you’ll really like this.’ Then he took a pack of cigarettes from his shirt pocket and offered me one.”

“Wow, thanks, Mr Goodman, I said, taking one of the cigarettes from the pack. He lit it for me and I puffed on it. I had smoked before behind my friend’s garage, but this was the first time an adult had offered me a smoke.”

“Then he put his arm around me and opened the photo album on his lap with his free hand. I couldn’t believe my eyes (and my good fortune!) The first picture was of a teenage boy with long hair wearing makeup and dressed in girl’s panties and bra and posing sexy for the camera. The boy’s cock protruded from the top of the panties.”

“‘You know,’ he said, ‘One day I could see you in your attic window. You were dancing around in a negligee looking damn sexy. Don’t be embarrassed, it’s perfectly normal and we have a lot in common. You like to dress and tease like a girl and I like watching.’”

“I couldn’t take my eyes off the picture and my cock started getting hard. Mr. Goodman must have noticed and he moved his hand down to my cock and rubbed it through my pants. I was tipsy and feeling so turned on by this elderly gentleman who seemed turned on by me.”

“He flipped to the next page of the album. Here was the same boy with his panties down around his ankles; he was jerking his erect cock.”

“Wow, my cock stirred some more and Mr. Goodman rubbed it and said, ‘Hey, I think you like these pictures as much as I do.’”

“I said, ‘Yeah, I do.’”

“Then he said, ‘Why not get up and take your clothes off, I think you’ll be more comfortable.’”

“I was trembling with excitement as I took off my sneakers and socks, then stood up and removed the rest of my clothes. My penis was hard and Mr. Goodman said, ‘Why, you’re more lovely than this boy we’ve been looking at. I’ll tell you what. I have a camera. How would you like to pose for me?’”

“Wow, it was like a dream come true.”

“‘Sure,’ I said. ‘But I have no clothes like the boy in the pictures.’”

“‘That’s okay,’ he said. ‘We’ll hop in my car and I’ll get you some clothes. It so happens a friend of mine owns a women’s clothing shop that has junior sizes. Here, have another sip of wine and we’ll get going.’”

“I took a sip from the glass he handed me, then put my clothes back on. We headed out to the car.”

“We drove off and soon arrived at his friend’s store. There were female mannequins in the window dressed in beautiful outfits.”

“We headed in and found a heavyset gentleman behind the counter. ‘Chris, this is Steffan.’”

“‘Why, scoot on back here and let me have a look at you,’ said Steffan.”

“So I walked behind the counter and Steffen, who was seated, pulled me onto his lap.”

“‘Say, you’re a hottie. You can call me Uncle Steffan.’”

“I was seated on his lap with my arm around his neck.”

“‘Give your uncle a kiss,’ he said.”

“I moved my lips to his and my wet tongue met his. As we necked, he reached down and unzipped my fly and moved his hand to the top of my underpants; he slid the front down, releasing my hard cock, which he slowly stroked.”

(To Be Continued)

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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