Pictures Tell the Story Pt. 03

This story has Non-consensual anal sex, bondage, cross-dressing with a twist and mild BDSM. If this is something you're not interested in, don't read. If it is, I hope you enjoy the story. Any suggestions. or comments are welcome.

Chapter 3 Shopping for a surprise.

I received a call from the man that had left the RSVP note. He said, I really enjoyed myself and I have a secret I want to share. Having a big dick isn't all it's cut out to be. I have dated and the moment a girl sees my cock, it's no way, and we break up.

There are a few guys who go, either way, it's the same. You were my first fuck. I really enjoyed it. I wanted to tell you that and since you agreed to do it again, I assume you were fine with me. We were amazed you could take so much, we enjoyed you for hours.

I hope I didn't hurt you. I replied that he had not but, the one who spanked my ass needs to go easier this time. I'm not sure I will heal in time for the weekend. I will bring something different to use. He said I'm sorry that was me. I was overzealous.

I was angry and frustrated, lost in the moment. My first sex was to take advantage of a stranger, that isn't who I am. You were like finding a treasure, I couldn't stop myself and I had to make sure everyone took part, otherwise someone would talk.

I told him it was ok, that I understood. I sure want to fuck you again he said. I can hardly wait until Saturday. I replied if you are that anxious, arrive a little early. I will be there around four so tell your friends to meet you at the spot, at seven.

I told him it took some time to transform into my alter ego, Michelle, but if he wanted a one on one, that would be ok. I don't want to wear you out before the party begins. He laughed and replied, no chance of that. I said You can help bind and get me ready for the boys.

He said fuck, that would be awesome. I will save up the entire week so I have plenty of stamina for the night. By the time they arrive, you will not even notice them and laughed. I will do something special to repay you for how I acted. I said that sounds like fun.

From the video, I was sure I knew what he had in mind. A blow job would start the evening off with a bang. Now I was eager for Saturday to arrive. I had to buy new items and plan a new adventure. This is going to be exciting.

I said, In return I want you to protect me. Make sure your friends don't decide to harm me. I was worried all night; it had dampened my enjoyment and been in the back of my mind. He replied, I will protect you, no one will hurt you, you have my word.

I said, cool, I am already looking forward to another night of fun. He replied, is there anything we did that you didn't like? I replied that everything that had happened was good for me, just go easy on the spankings. He replied I will.

With that, the conversation ended with, see you Saturday. I planned to take a riding crop. It hurt as well but didn't damage my ass as much. I would have to be careful to hide the bruises. My wife would shit if she saw them. She would have questions I didn't want to answer.

I went to work on Tuesday, business as usual. Wednesday we made supply runs to another city, about 100 miles round trip. Normally, someone from the office would go, but today, I informed them I would make the trip myself. I had additional shopping to do.

I know a shop that caters to my needs. It is run by an attractive, trans girl, long auburn hair, fair-skinned, and well dressed. She is always warm and friendly. I spend a lot of money in her shop, and she carries all the items I would ever need.

All I had to do was ask for what I wanted and she would pick out clothes to choose from. There is a dressing room with a full mirror. It was much better than buying online, or trying to buy in the female section of shops, never questions or judgment.

She wore turquoise jewelry and if I had to guess; she had some American Indian in her. Nice breasts, slim-waisted, full hipped, and on any other occasion, someone you would want to get close with. Her laugh puts you at ease.

She greeted me with a big smile and asked what I was looking for. I told her, a complete outfit, head to toe. I wanted everything in shades of blue. Hose, garter belt, crotchless panties, bra, sexy skirt, and midriff top, silk or satan, please.

If you have anything else that might improve the outfit, I trust your judgment. I want a riding crop as well. She said she would see what she had. You can browse or go to the changing room. I thanked her and decided to look around.

I found a light blue fuzzy set of handcuffs; they had a hidden switch that would release when I wanted and put them into a basket. In the same area, I found a blue mask and choker, I took them in as well. The choker would conceal a surprise.

While doing business shopping I picked up a specialty order I had placed a couple of weeks before. It was a voice emulator that could be set with a variety of male or female voices. It could be attached to a choker and remain hidden.

Bobby was taking items into the changing room. I asked if she had time to put nipple holes in a bra? I want them smaller than mine. She said sure thing, sweetie; Step into the dressing room, take off your shirt and I will measure the center of your nipples.

She said, I see you have small breasts, would you like a bra that would push and help form you? I said sure, trusting she would choose something perfect for me. I found a clothing bag that would hold all my new items and fit the backpack.

I tried everything on and was pleased that I looked pretty sexy for a guy. I asked Bobby to step in to give her opinion. She looked from every angle and asked if I wanted to hide anything? I said no a birdcage that will take care of that.

She said you're a knockout. I hope whoever this is for, appreciates the effort you are putting into this outfit. I thanked her and told her how great she was for helping me. She smiled and gave me a kiss on the cheek. Hove you have fun, sweetie.

She packed everything in the clothing bag. I paid and tipped her for helping. She said you don't have to do that. I replied it will hurt my feelings if you refuse. She gave me a warm smile and accepted saying see you next time and thanks for shopping at my shop.

Recent events made my mind go to mew places. She was beautiful, but I was pretty sure any guy who dresses up as a female isn't thinking about whom to fuck, they want fucked. I have no desire to fuck anyone other than my wife.

My appearance was ready to go, Michelle was going to be stunning. These boys had taken advantage of my situation. This time, I would be dressed to stun. I wanted everyone to get an instant hard-on the moment they saw me.

I feel guilty. This time it was me, taking advantage of them. They are young. They walked around all day with a hard-on, searching for a place to stick it. Youth is a wonderful thing. As long as they wanted what I offered, we could go camping every weekend.

After this weekend I would own them. I would never tell them I knew who they were. As long as they thought they were getting something, sex with no strings attached, I expected them to take full advantage of a good thing. I consider myself the winner.

The week went fast; I tried to concentrate on work, but it was hard. Friday afternoon I arrived home and my wife called. She said I have to fly out of town to handle a problem and will miss sex, but hoped it will make you extra excited when I get home.

I told her; you got that right. I told her I had been thinking about her all day and had a raging hard-on. She laughed and said, save that for me, please. We laughed, I told her to be careful and that I loved her. She said the same.

I love my wife; we have a great marriage; we are perfect for each other. I have a peculiar need and desire. I don't want to become a full-time cross-dresser, but my part-time dressing fulfills a need that our marriage doesn't.

It won't matter where I get my appetite, she will love the way I eat dessert. Last week I was fucked and forced to eat cum. Looking back, that qualifies as shit happens. I am not fucking anyone except my wife, she is the only woman I perform oral sex with.

It would have never happened by my choice or design. It was a random act of fate. Now it doesn't matter, I agreed to repeat the experience. It will be the same circumstances, conditions, and players. The best results from a random event.

I had seen my doctor. Tests were run, no STD's. That was a load off my mind. Had someone infected me, it would have changed everything. So I am good and excited about what the weekend will bring. Never had more fun dressed up. It changed me a little.

With more time on my hands, I watched the video again and looked through my new clothes. I was going to hand wash everything, wanting them fresh and clean. As I looked through the clothing bag, admiring each piece, I took out my crotchless panties.

When I held them up, a note and a photo fell out. Picking them up, the picture was of Bobby with a huge hard-on. Her dick was twelve inches at least, it looked bigger than any dildo in my collection. The head widened like a mushroom then tapered to the tip.

She was dressed as I had seen her at the shop; the photo had been taken in the same dressing room where she helped with my appearance. On the back, she had written, love your small breasts and ass. Wish you were dressing for me. A red kiss was pressed below.

Her cock would be hard to fit in my mouth. The note read, hope this you don't mind. I flirted with you yesterday, but you didn't notice. From the way you dress and the mention of a birdcage, I gather you are a bottom. If you would like to meet sometime, I am a top.

Call me if you are interested, followed by her number. Damn, fate is on a roll, lucky me. I grabbed my cell and immediately called her. She answered in a cute female voice. I said this is Michelle, you helped dress me earlier this week, just found your note and picture.

She replied, oh, I thought you weren't interested; you didn't call. I told her, would love to get to know you better if the offer is still on the table. Sorry, I have to be careful when I look through my things at home. I just opened the clothing bag.

She said, well I don't know. I have been so disappointed this week, but as long as you don't mind being punished for making me sad, I guess it would be ok. What do you say? I said you can do anything you want with me. She giggled, saying, how do you want to meet?

I replied, at your place if that would be ok? She said sure sweetie, When? I said well I have confirmed plans for the weekend, I can't get out of that. This evening free, but I need to get back early, it's 100 miles round trip to your city.

Asking where I lived, I gave her the name of the town. She said, well you are in luck, I only live 15 minutes from you. I have a home close by and commute to the city. I asked what time? How about now? I told her I would need a little time to shower and change.

I told her I had just got off work. It was a little after five, so she said, how about six? I said sounds good. Why don't you bring your outfit, I will help you get dressed if that is ok with you? I said sure, that sounds like fun.

I told her, never dressed for anyone, ever. Until recently only you have seen Michelle. I have always dressed up for myself. I like to take video and photos. I get a great deal of pleasure with toys and such. She said she would love to see some of those.

Then she exclaimed, oh my, I might be too much for you. I said you have my word that if it doesn't fit; you have permission to continue as long, and as many times you want until it does. I will work to make us a perfect fit.

She laughed and said, you better get a move on it. You don't want to be late. There would be consequences if you were. I said I will try to be a little late then. She laughed and said, bad girls, need to learn who the boss is. Laughing, I and said ok.

I got her address and directions. It should be easy to find with Onstar, I told her I would be in a black BMW Ragtop. She said I will be watching for you. I will keep the garage door open, just drive in and park, see you soon.

As I took a shower, I couldn't help but think how the past ten days had transpired. The weekend of unexpected adventure, followed by a surprise invite from a beautiful girl, another new experience. Shit, I hope my run of luck doesn't backfire on me.

I was way outside my realm of experience and playing along one moment at a time. From closet cross-dresser to slut. I would have never put myself in this position, even in one of my fantasies. I have high expectations that tonight was going to be wonderful.

I wore my cock restraint since she knew that I did. I cleaned myself thoroughly and put on a flesh-toned Armor Tug, butt plug, and ring. As I dressed, I took the flash drive with the movie. I wanted to be upfront and let her know what happened.

I would also let her know that I had been tested and was free of any problems. The idea of showing anyone the movie was both exciting and scary. That it was out of my control might enrage her or excite her. I would find out later.

I smoked a bowl, put my pipe and a container in the backpack, and headed out, I arrived at her house at 6:05; she was standing outside and the garage doors were open. I parked my car, the doors closed and I went into the house.

I was impressed with her home; it was big, luxurious, tastefully decorated, and spotless. I met her inside and told her. You have a beautiful home. Business must be good. She said, thanks for saying so, I work hard to keep everything in order.

She stepped up to me, gently kissed me on the lips. Welcome to my home. Make yourself comfortable and I will bring some wine. She returned with a 1969, Riesling. A great vintage of fruity wine. I had tasted it before and it was one of my favorites.

I thanked her, and she said; I see you brought your outfit. I am so happy you did that. I said, let me say something, I definitely picked up on your flirt. I didn't respond because you are a beautiful woman. She said I don't understand.

I said I thought that you dressed that way for the same reason I do. To be penetrated, I have no desire to be the pitcher; I am a catcher. She laughed and said, you're so sweet. I understand your confusion and I am glad that we figured it out.

Then I said, so you know, I went to my doctor this week and had tests to be sure I am safe. You have no worries; I hope you won't need a condom. I want to feel the real thing. She said, well it so happens, I am also STD free. Then she gave me a wink.

She asked you are sexually active, right? I said until last weekend I wasn't. Unexpected things happened. She said, do tell. You have stirred my curiosity if you don't mind sharing. No pressure. If it would make you uncomfortable, I will understand, sweetie.

I began telling her about the outing, how I set up and dressed in the outfit I had purchased at her store two weeks prior, all the particulars. She said, oh I so wish I had been there, and giggled. I said, actually I am glad you weren't.

She got a sad, pouty look on her face and said, Why? I said I was enjoying the feeling of being helpless. I posed in that position for an hour. Massaging the butt plug in my ass, enjoying the random shocks to my nipples and the taste of cum in my wife's panties.

She said, ok, but I still don't understand why you wouldn't have been happy for me to be there? I said, after that hour reality interrupted my perfect isolation. It took a moment for her to digest what I had said and then, oh my god, someone found you there, right?

I said yes; It is all on the video if you would like to watch it. Then you will understand why your presence would have been bad for you. She said ok in a serious voice. I said the choice is yours, but you might find it disturbing or you might find it erotic.

She scooted close to me on the couch. I gave her the flash drive and using a small remote, pressed and an entertainment center dropped from the ceiling. She plugged the flash into the side, returned, sat beside me, and held my hand, starting the movie.

She commented on how great I looked and how prepared I was. She said you look completely innocent and vulnerable. I told her to fast forward a bit, she would know when to stop. She did, when the two men moved to my head, she watched as they pulled the wrist straps taught.

She paused and said, oh my god, they are going to use you, right? I said that and much more. Did they hurt you? I said a little, but overall I ended up having a good time. It could have gone bad, but it didn't. Watch to understand.

She watched, fast-forwarded, watched then said, oh don't tell me they are going to do that? I said yes; they did. She watched as they poured cum into my mouth, then beat me with the strap. That is awful, you poor thing. I said I got through it in one piece, so all good.

She stopped the video and asked, how many were there if you don't mind talking about it? I said there were twelve young men. they each had their way with me twice. That they had emptied eight cups of cum into my mouth. They used me for nine hours.

Tears welled up in her eyes as she hugged and kissed me. I said now you understand why I would never have wanted you to be there and gone through what I did, but to be truthful, I enjoyed most of it, although it was my first time.

I said that I had never considered having someone fuck me. It was impossible for me to even think that was possible. Although they took advantage of me and used me. It awoke something inside me I had no idea existed. The feeling of real penetration was incredible.

She said, I have allowed no one to do that, but I understand that need in some girls. I am glad you survived in one piece and I would never hurt you or take advantage of you the way they did. I said you can do whatever you like to me. I really am attracted to you.

Then she said, drink up and let's get you all dressed up, sweetie. I want to make this a very special evening for you and we will see if you want to return for more. I haven't been with anyone in years and I just had to take a chance with you. Seeing you in the dressing room.

she stopped, and I said; I saw the picture, trust me, the attraction goes both ways. It's a shame we didn't get together before last weekend. I would have loved for you to be my first. I wouldn't have been in the woods, I would have been with you.

She said, I hope you feel that way after tonight, I said, I can't think of anything that could change my mind. She knew I was happily married. We had chatted a bit on my visits and I know that she understood, I couldn't be with her all the time.

We finished our wine then I asked, do you smoke pot? She said, on occasion. I said I can't think of a better time than now. She laughed and said sure. I told her, this is superb, it works on the body and makes you feel so good, it doesn't mess with your head.

It wasn't long before we were both feeling good. She commented, your right this is the best I have ever smoked. I told her I would leave her some so she could enjoy it when she wanted. She told me I was too generous but didn't object.

She got up and took me to her bedroom. Once there she removed my clothes and dressed me. It was enjoyable to have someone change me into Michelle. Especially since she specialized in selling cross-over garments. It didn't take her long to have me looking like a girl.

She knew my name was Michael, and that my alter ego was Michelle. She said she liked it; it fit my personality. She left herself and went into an adjoining room. She was gone for about fifteen minutes. When she returned, all I could do was marvel at her transformation.

She was dressed in black leather. Hip boots, open bra, gloves, crotchless panties that left her open for me to see. She walked up and said, see anything you like little girl? I said yes, can I touch it, please? Of course you can, on your knees. I obeyed.