Not What I was Expecting



Another boring night. My name is Steve. I moved to Arizona a couple years ago. As so common, another divorce man, 51, in decent shape but living comfortably without many aggravations at the moment. My problem is that I can’t stop having the same thoughts in my mind so often. Thoughts about the kind of woman I desire to meet.

I lived in Vegas for almost 30 years and with my youth being in the 80’s and 90′, it was rock and roll, drugs and lot of play. I was no Casinova but I had my share of adventures. I found a lot of pleasure in pleasing women and of course being pleasured. It was strictly straight sex and in, truth, not very kinky but it was still a lot of fun. There were threesomes and even more a couple times. Like I said, enjoyed every minute of it, ok most minutes of it.

When I got into my late 30’s I got involved with a woman and for the next 15 years I lived a life that I’m sure a lot of you are familiar with. The sex dwindled to the point we might as well been married. Later in this relationship, I got into reading a lot of the erotic stories that are online and watching some videos when the time presented itself.

The porn at the beginning was rather vanilla but as it continued I started reading more stories that involved various kinky behaviors. I had always enjoyed women who dressed provocatively. I mean, what would you rather see? A naked woman or a woman in a corset, garters, nylons, fuck me heels. Yea, right, I know. I started watching a lot of videos with women dressed in this manner. I have to confess that none turned me on more than a woman in a black corset her garters stretching her seamed nylons high on her hips. Black boots or pumps with four inch spike heels would adorn her feet. Panties so sheer you can’t keep from staring. Then the makeup, especially the eyes that seemed to look right through you.

You can probably guess where this is heading. You would be right. These women usually had a man kneeling in front of them willing to do as told, willing to be used, or abused by these women. Dominant women. I started reading more stories involving feminine domination and couldn’t believe how some of them made me feel. What would it really be like? Could I do what the men in these stories did? I got into reading some of the stories involving cuckolding. I had never heard of it and had no idea that women enjoyed that and really couldn’t believe how much it seemed the man liked it. Damn, don’t know if I could do that.

Then got into watching the videos and reading the stories about bondage and discipline, especially the ones where the woman was in charge. What must it feel like to be bound to where you can’t stop whatever might happen? What if it hurts too badly and you can’t stop it. What must that feel like? Scary I believe to a degree but I couldn’t stop thinking about it. How would I react? Why did I feel like I wanted to find out?

Finally, the woman I was living with and I parted ways. Very amicable, which was good. The problem now was I had nothing from stopping from doing more than just watch videos or read kinky stories. Was it best just to leave it in my fantasies? I resisted for awhile but once I discovered craigslist, I knew what had to happen. It wasn’t long till women could read this ad on craiglist.

‘Middle-aged single man would love to meet a dominant woman

who likes being in charge. Very inexperienced but willing to try

anything once, more than once if told. I’m divorced, live alone and

can host. Have been reading stories and watching videos involving

smbd themes and very curious about it all and how I would reach.

If you are that special lady, please reply.


I can’t tell you how nervous I felt after posting this ad. It was about 3 days later

when I got my first answer. It sounded promising, so we decided to meet for

drinks. We met on Friday night at this nice bar. We introduced ourselves, her

name was Jessica. She was only about 40 and was attractive. Her outfit was sexy

but not over the top and not dominating looking at all and I was rather glad about

that. I was nervous she would show up looking like a hooker, making me look like

a john. We had a drink and made small talk for a short time.

I was looking at her and she had almost a smirk on her face when she looked at

me and said, ‘You look like you might be gay. Lot of submissive men turn out to

be fags.’

I couldn’t believe she just came out and said that. ‘No I’m not gay, I’m totally


‘Look at me when you answer me Stevie. It’s ok if you are. Fag boys can so much

fun. But you are way too manly for that, aren’t you Stevie?’

I look up at her and her face doesn’t look like she’s joking around with the questions. ‘I’m not a fag, ok.’

‘Don’t get prissy with me Stevie. You’re the one wanting to meet a dominant

woman, show me respect. Apologize.’

Damn, don’t think this is going well. ‘I’m sorry, I’m just not used dikmen escort to people

accusing me of being gay. I’m sorry Jessica.’

‘Call me Miss Jessica and get up in front of me, head down and apologize like you

mean it.’

I can’t believe what is happening. Maybe I should just go but I don’t. I slide out of

the booth and go to her side and stand there, lower my head. ‘I’m really sorry Miss Jessica. You just kind of surprised me with that gay stuff. I’m really sorry and I hope you will forgive me.’

‘Go sit down,’ she tells me and I do. ‘How did it feel Stevie, standing there

apologizing to a woman you don’t even know. A woman who told you she

thought you looked gay.’

‘I have to admit it was embarrassing Miss Jessica.’

‘What if I would have told you to get on your knees to apologize Stevie boy?’

‘I don’t know if I could have done that Miss Jessica. Discretion is important to me.’

‘You don’t want others to know that you are a submissive boy Stevie?’

‘No Miss Jessica, I was looking for something private and discrete.’

‘Good submissive boys don’t worry about what they want. There is only one thing

important to them. I know you know what that is Stevie. Tell me.’

I look down, quietly, ‘They should want to please and obey their Mistress.’

‘Good boy, your answer to my earlier question should have, “I would have

got on my knees and apologized to you Miss Jessica. Do you understand Stevie?’

My head spinning. I’m starting to realize this isn’t fantasy roleplay like I was

thinking about. This woman really is dominant and is testing me to see if I’m

really serious about this. ‘Yes Miss Jessica, I understand but this is all so new to me and I’m trying, really I am.’

‘I understand boy, I want you to do something for me. Do you think you can do


‘I will try Miss Jessica.’

‘No Stevie, can you do this for me?’

Nervously, ‘Yes Miss Jessica, I will do it for you.’

‘Good boy,’ she says as she takes a pair of lacy pink panties and places them on the table in plain sight. ‘I want you to go into the men’s room and put these on and throw away whatever you are wearing now.’

I just look at the panties in shock then quickly grab them before anyone sees them. Looking around I see a couple middle aged women leaning over whispering

to each other and looking our way. ‘Really Miss Jessica?’

She looks over at the two women and smiles. ‘Yes really Stevie. I expect boys

I spend time with to be in panties. It seems to help their attitude. I mean, really,

how can a guy feel much of a man if he’s sitting there in panties. Now go, and

Stevie, take a nice picture with your phone showing your pretty panties so you

don’t have to pull your pants down out here to show me you did as told. Now


Again, I feel like I should leave but I don’t. I get up shoving the panties in my

pocket and go to the men’s room and get into a stall. It’s all rather scary but also

exciting, almost feel like I’m in one of the stories I always read. God, the way she

talks to me, I can’t help myself from being turned on by it even though she’s being

pretty aggressive. I take my slacks down and take off my white jockeys and slide

the pink panties up. They feel so slick and soft against my cock and I can’t help

but rub lightly, feeling my cock through the silky material and I realize how nice it

feels. Embarrassed when I realize what I’m doing and put my slacks back on. I

can feel the panties holding my cock tightly. I get ready to leave the stall when I

remember the picture. I pull my slacks back down and hold up my shirt getting a

clear picture of the panties. I dress again and look at the picture. You can see my

cock through the material and I’m surprised how small it looks in the picture. Damn, this just gets more and more embarrassing.

I go back out and sit down, hoping my face isn’t as red as it feels. Take a big drink

after seeing she had ordered us another drink. She tells me she wants to see the

picture so I hand her my phone with the picture showing. She laughs as she looks

at it.

‘That’s so cute, I think pink might be your color sweetie. And will you look at the

little cock, it’s just darling. I can see why you might like dominant women now.’

Just sit there, don’t know what to say. She keeps looking at the picture, then at

me, smiling. She looks over at the two women, they are whispering across the

table with each other.

‘I bet they would love to see this picture Stevie, don’t you think so?’

‘Please, please don’t show them. Please.’

‘I thought we talked about this and what was important Stevie. If it would please

me to show them the picture, what should I do?’

I don’t know what to say. I just keep my head down and keep quiet.

‘Look at the ladies and smile Stevie.’

I emek escort force myself to look up and look at them. They are both watching us.

‘You do want to please me don’t you Stevie?’

‘Yes I do Miss Jessica but do you have to show them the picture? It would be so

embarrassing. Please Miss Jessica.’

‘Ask me to show them the picture of you in your panties Stevie. Now.’

The look on her face tells it all, lowering my eyes, ‘Will you show them the picture

Miss Jessica?’

‘What picture Stevie?’

Realize she is trying to make it even more humiliating. ‘The picture of me in my

panties Miss Jessica.’

‘Sure sweetie.’

I can’t believe it when she actually gets up and goes over to their table and shows

them the picture. They both look at me and start laughing. Miss Ruby sits down

and they talk quietly every once in a while they look over at me. I wonder what

she is telling them. Finally she comes back.

‘That wasn’t so hard was it Stevie. I told them you wanted them to see the picture. They thought your little cock was so cute and I know it’s embarrassing for you so I told them you were gay so it didn’t really matter that your cock was so small.’

I can’t look at them. I feel so humiliated.

‘How does it feel Stevie? Is it like you imagined? I doubt it but you needed to see

what it really like to be treated as a submissive. You did quite well. Most men would have walked out of here a long time ago. But not you Stevie, you were a good boy, went and put on a pair of pink panties like some sissy boy, took a picture of it, which I did send to my phone, and asked me to show the picture to some strange women. How does it feel Stevie?’

‘I don’t know. To tell the truth, I’m a little overwhelmed at the moment. What

you asked of me was hard for me to do but I didn’t want to disappoint you. It was

so different feeling like I did. It was embarrassing and humiliating but it also was

exciting and scary, and I have to admit, it was a turn on too.’

‘Good boy, here’s my card. Call me next Friday at 6:00. We will be going out that

night so don’t make any other plans.’ She gets up and walks over to stand in front

of me. ‘Look up at me Stevie.’

When I do, she slaps my face hard then turns and walks out like she is mad at me.

I look around and see the two ladies and others looking at me. My face really

stings and I want to rub it but quickly get to my feet and get out of there as

quickly as I can. I get to my car and sit back, not believing what just happened. I

look at the card. Do I dare call her Friday?

I drive home, go in and sit down in my favorite chair and think about the night.

Unbelievable is the only word coming to me. I light up a joint and sit there and

smoke the whole damn thing as I go over it in my mind over and over. Then I

remember and open my slacks and see the pink panties. I can’t believe I did that

and that she showed the ladies the picture. I bet they really think that I’m gay, I

mean, I am wearing pink panties.

Why is my cock hard? Did doing this really turn me on? I realize it did and I find

myself standing and undressing only leaving the panties on. It feels so good when

I rub it through the panties. I close my eyes thinking about the night, the way she

talked to me, the things she made me do. Suddenly, I know what’s going to

happen and I can’t stop it. I come hard in the panties, one of the better orgasms I

have had in a while. I just lay there in my cum soaked panties till I start falling

asleep and get up and go to bed. I leave the panties on.

I couldn’t stop thinking about her and what happened all the next day. What did she have in mind for me and was I getting in over my head? It would probably be best if I found a way to end this before it gets out of hand. I had a lot of trouble concentrating at work and was so glad the day was almost over. As I was getting ready to leave I received an email on my computer. I didn’t recognize the sender and couldn’t believe it when the subject of the email was ‘bad boy.’ How did she know where I worked and how did she get my email address?

I opened the email, it was short and direct. ‘Go to Victoria Secrets and buy seven pairs of panties with at two of them being thongs. Buy two pair in pink with one being a thong, one in black, one in white and surprise me with the rest. Make sure all are sexy and fit you or I will take you there myself next time. Send me a copy of the receipt. If I don’t receive the copy by Thursday, I will post my favorite picture of you on all the computers at your work place. I wonder how they will feel knowing they are working with a sissy. Now be a good boy and do as told.

Mistress Jessica’

Fuck, fuck. How did I let myself get into this position? How could I do this? I don’t have any idea what size, maybe I can find out on some internet sites. eryaman escort Will the women working there will be thinking that they are for me. I made sure the email was deleted from the computer before I left. Driving home I felt like things were getting out of control. I was just looking for a little excitement in my life, that was all.

Well, I did it. I can’t tell you how embarrassing it was. The clerk at Victoria Secrets was probably about 35 and was very attractive. I told her I was buying the panties for my girl friend but I don’t think she believed me. I know my face being red from embarrassment didn’t help anything and the way she kept looking at me with a smirk on her face. As I left, she said that she hoped that I would enjoy my panties. That was all so humiliating.

When I got home I mailed her the receipt. An hour later I got an email back telling me that I was being a good boy and that she was proud on me and that she couldn’t wait to see me in them. She gave me an address and told me come to that address at nine o’clock on Friday and to wear a nice pair of slacks and a dress shirt that we would be going out. She told me to make sure and wear your new pink panties.

It was only Wednesday and I had to worry about it for the next two days but I couldn’t think of any way to get out of this. Finally Friday arrived and I was a total wreck at work. After work I went home, smoked a big joint to try and help me relax but it didn’t help much. When it was time to get dressed, I slide the pink panties on and had to admit that they did feel nice. Luckily, they seemed to be the right size. I went to the mirror to see how they looked I was surprised how obviously my cock was displayed. Damn, I wish it looked bigger. I put on a pair of black slacks and a long sleeved black shirt and got busy working up my nerve. I have to admit I was a nervous wreck by now and smoked a little more weed to try and help me through this.

I drove to the address she had given me. It was a high end high rise apartment building and I went up to her floor and knocked. I was surprised when a man answered the door.

‘You must be Steve, please come in, Jessica will be here soon.’

I followed him in not believing what was happening. He looked to be late 40’s to 50’s and reminded of the pictures of top level executives you see in the magazine. He was probably about 5’10”, slender, his hair light brown and pulled back into a pigtail.

‘My name is Matt’, he says extending his hand. We shake and the softness of his hand surprises me. “What can I get you to drink Steve? I’m having scotch.’

‘That will do,’ I answer still trying to deal with the fact that I’m standing here with another man and not Jessica. He leaves to fix our drinks and when fixing mine he put in several drops of Jessica’s special formula. It is similar to the way Viagra makes you feel, the heat in your body, the feeling of arousal strong, but opposed to Viagra it makes it almost impossible to get an erection. He comes back with our drinks and sits on the other end of the couch from me. I assumed he would sit in one of the soft chairs and seemed weird he would join me on the couch.

‘Jessica said I should ask you about how you two met.’

That is the last thing I wanted to discuss but I didn’t want to do anything that would make it worse when Jessica arrived. ‘We met on the internet and then met for a drink at a bar.’

‘Jessica is a special woman. I hope you realize how lucky you are that she has decided to spend some time with you.’

‘Yes, she made quite an impression on me.’

Laughing, ‘I bet she did.

‘What do you do for a living Steve?’

‘I work for an accounting firm. How about you Matt?

‘I’m a fashion photographer, I have a book containing a lot of the pictures that I have sold if you would like to see them.’

‘Sure, that sounds great.’

He leaves and comes back with a large book and sits next to me on the couch putting the book on the coffee table in front of us.

‘Go ahead, check them out Steve.’

I start looking through the pictures. They are pictures of beautiful women in gorgeous dresses and the quality of the pictures is outstanding. Figure he must be a very popular photographer. He is leaning next to me and I can smell his cologne. As I look through more pictures they start becoming more erotic. The makeup becomes more seductive, the clothes changing from one scene to another. One woman looks shy and embarrassed. The next picture she is there standing meekly in front of a woman in black leather. I’m shocked when I realize the woman in leather is Jessica. I can’t stop staring at her.

‘I know how you feel Steve. She does have a presence doesn’t she?’

Realize how long I have been staring and quickly turn the page. The next picture is of a man standing there looking back over his shoulder at the camera. The only thing he is wearing is a pair of black jockey shorts that fit tightly outlined his ass. He looks to be mid 20’s black hair, five o’clock shadow and is a total stud.

‘His name is Tony. Gorgeous isn’t he?’

Realize that I’m staring again. ‘Yea, I guess if you are into that.’

‘I could introduce you. We are good friends. I bet he would like to meet you.’

‘No, that’s ok. I’m not gay.’

‘Neither is he but he does like gay men.’

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