Cuckold Strap On Cross Dressing Sex Story August 19, 2008
Posted by sexstory in Cheating Wife Stories, Cockold stories, Crossdressing Sex Stories, Crossdressing Stories, Cuckold Stories, Domination Sex Stories, Femdom Sex Stories, Forced to Feminize, Kinky Sex Stories, Older Women Sex Stories, Role Play Sex Stories, Romantic Sex Stories, Sex Fantasies, Sex Stories, Sex Stories For Women, Sex Story, Straight Sex Stories, Strap On Dildo Stories, Taboo Sex Stories.Tags: cross dressing, cuckold, Sex Story, strap on
trackback
Cuckold Strap On Cross Dressing Sex Story
Cuckold Strap On Cross Dressing Sex Story – Mother in law with strap on dildo turns husband into cuckold cross dressing sissy slut.
Written my Bob for kinkysexstories.org
I began cross-dressing when I was a teenager. I just enjoyed the way the soft and frilly things felt against my body. I was never gay or attracted to me, but I loved women so much that I wanted to be more like them. So although I was a closet cross-dresser, that’s as far as it went.
When I met my wife Brandy, I told her about my lingerie desires and after awhile she understood that it didn’t threaten our relationship, but in fact drew us closer and allowed us to share something very special. Since my wife accepted my cross-dressing, I knew she was the girl to marry.
My wife’s mother Alice was a very dominant woman and never liked me from the start. My wife told her mother everything we did, even our secret about my cross-dressing fetish. I was hurt by this breech of trust but what could I do? For a wedding present, my mother in law bought me a blond wig, pink panties, and red pumps to match. I was completely embarrassed and humiliated when I opened the gift while my mother in law just smirked at me and my wife giggled.
What was worse was when I discovered that my mother in law would be going with us to Miami on our honeymoon.
“You know mom. She does what she wants to do and no one can stop her.” My wife said.
The first day we arrived, my mother in law informed me that she had bought my wife a day at the spa and that would giver my mother in law and I a chance to bond and go shopping together.
cross dressing cuckold
“Oh stop putting up a fuss.” My mother in law said. “If you come with me and are a good boy, I just might by you some more sexy outfits for your honeymoon.
Both my mother in law and my wife laughed at me but she had a point. The idea of buying women’s clothes for me to use on my honeymoon did kinda turn me on. So I went along with it.
I was taken directly to Victoria’s Secret and led in my the hand of my mother in law. She marched me right up to the counter where a beautiful young blond was standing.
“Hi, this is my sissy son in law and he loves to dress up like a sexy woman. He is on his honeymoon so can you help us find something fabulous for him to wear tonight?” My mother in law said.
I was so embarrassed as the two women smiled at me. After the sales girl picked out a few items, my mother in law escorted me into the dressing room and began to strip me naked.
“I can do this alone.” I said.
“Oh stop your sissy fuss. You know you enjoy this so shut up.” She said.
I kept quiet as she took off all my clothes.
“Now turn around and let me look at you.” She said as she spun me around to look at my ass. “Bend forward just a little and stick out your butt. Very nice. Your not hung very well, but that’s ok, I doubt you will be needing that equipment much anymore. But I love your ass. It’s very inviting.”
“What about your daughter. How would she feel if she knew you were looking at me in this way?” I asked my mother in law.
“Well my sweet thing, it’s going to be our little secret for now. But after all, mommy knows best. Don’t you worry about that. I’m doing this for her anyway. She is going to be very excited about the wedding gift for her.”
My mother in law spanked me gently and then told me to step into the sexy outfit she had picked out for me. After I tried it on she stood behind me and we looked in the mirror together at how sexy she had made me.
“There, now that is nice isn’t it? Tell mommy how much you like her attention and how lucky you are that she can do this special thing for you.” My mother in law said.
“Yes, it’s true. I do look very sexy and pretty in this outfit. Thank you Alice.” I said respectfully.
To my surprise, Alice took my face in her hands and kissed me on the lips using her tongue. My cock began to grow out on my panties and she reached down and stroked it.
I skrimed back and said, “Hey, what are you doing to me?”
“Just warming you up sweetie, that’s all. Now shut up. We need to buy you some make up don’t we? And maybe some perfume as well.”
My mother in law undressed me, then purchased the sexy lingerie for me, then took me to buy make up and perfume. The whole time I was thinking about our kiss in the dressing room. It had really turned me on but was it cheating or just flirting? Perhaps it was ok because it was my mother in law. Would my wife be upset? Like she said, Alice is going to do whatever she wants and there’s not much you can do about it.
Back at the hotel, my mother in law unwrapped the sexy clothes we had bought while we waited for my new bride to return from the spa.
“I’m going to run you a nice warm bubble bath, then wash you, then lay out your outfit for this evening.” She said.
My mother in law kneeled next to me while I soaked in the tub then she carefully stroked me with a sponge inspecting every inch of my body. My cock began to grow as she watched it. There was no way of hiding from her how much this was turning me on. I felt totally exposed and at the same time, totally hot. She was really turning me on.
“Ok sweetie. Time to get dried off and dressed up in your new sexy things.” My mother in law said as she patted down my body with a towel. I stood there with a raging hard on and said nothing.
My mother in law began to dress me up. First pink panties, then the pink bra, then the white stockings over my legs, then the teddy over the bra. Then she strapped on my red high heels, then placed a blond wig on me. Then she began to apply make up and lipstick. And finally perfume.
“You look gorgeous. Simply fabulous. You turned out much better than I thought you would darling. Don’t your feel great now?” She asked.
“Yes, you did a good job. Thank you.” I said.
“Now stand up and lets get a better look.” She said.
I stood up and my hard on was sticking out of my panties. My mother in law quickly grabbed my thobbing cock and said, “We must do something about that. It doesn’t look right no does it? Not very girly.” She said and led me to the bed, bent me over her thigh and began to spank my pantied ass. “Maybe this will help.”
After spanking me for awhile, she turned me over to find my cock was every harder now. There was no hiding how turned on I was.
“Well, that didn’t work at all. But I know something that might do the trick.” She said.
The next thing I knew, my mother in law had tired my hands together. Then she reached into her purse and took out a large strap on dildo and strapped it on.
I began to protest. “What are you doing?” I asked.
“Hush sweetie, you know exactly what I am going to do to you, and you know how much you want me to do it to you. So just relax now.” She said as she slipped two lubricated fingers into my virgin ass.”
“I;ve never done this before. Don’t you think your daughter is going to be upset? What if she finds up like this?” I asked.
strap on cuckold
“I’m going to have to break you in first. This way, when my daughter does this, you will have some experience and not be so skittish.” She said.
My mother in law bent me over and inserted her large strap on into my ass. It was very painful at first but as began to thrust into me, it began to feel much better. Then it began to feel wonderful. I looked into the mirror and saw my mother in law fucking me and it was too much.
“I’m going to cum now.” I said as I shot my load out of my panties and onto my pumps.
“Did the little sissy like it when mommy put her cock in your ass?” She asked me. “Come on, tell me how much you enjoyed that.”
“Yes, it felt very nice. I liked it very much.” I said.
“That’s a good little sissy slut. And we finally got rid of that hard on of yours too.”
“Just don’t tell my wife what we did ok?” I pleaded.
“Why not? Don’t you think she should know what a little sissy slut you really are? And how much you like it in the ass? I’ve been recording the whole thing so I can show all my friends what a little sissy my daughter married. I can’t wait to show them.” She laughed.
cuckold
“You recorded it?” I was horrified. “Please don’t show it to anyone.
“I bet your boss would love to see it and show it all around your office.” My mother in law threatened.
“Why would you do that? What do you want from me? I’ll do anything, just please don’t show anyone that tape.” I begged her.
“I am going to make you a cuckold sissy slut husband for my daughter. And you will also be my own personal sex slave. I’m going to pimp you out to my friends. And then make you watch your wife get fucked by a real man.” My mother in law said as she began to take off her skirt and panties. I was shocked. As it began to sink in, I realized there was nothing I could do. She had me over a barrel. If I didn’t do what she wanted, she would send that tape to my office, or even my parents. I would have to go along with her until I could think of some way to get out of it.
“From now on, you are not allowed to fuck my daughter. That;s going to be reserved for real men. I don’t want some little sissy slut to get her pregnant. We will find a stud for her and you will raise their children. If I find out you have fucked my daughter, I will send this tape to everyone you know, is that understood?” She said.
“Yes” I said helplessly.
My mother in law slapped me across the face several times and then looked at me as I began to cry little a baby.
“There there now. It’s going to be ok. In fact, you may even start to enjoy our new role as my sex slave. ” My mother in law said and then kissed me until I stopped crying. She began to stoke my cock and get me hard again. Then my mother in law forced me down to her mature and soaked pussy and told me to lick her until she came all over my sissy face.
It was very difficult for me NOT to fuck my new bride. She was a very sexy woman and I loved her very much. I bought her a dildo and explained that I was having difficulties in that department and was sorry. Meanwhile, my mother in law would secretly come over while my wife was at work and dress me up as a woman and fuck me in the ass. I must admit that I enjoyed it very much and I would cum very quickly.
My mother in law had arranged for my wife to get bi-weekly massages from a big stud. My mother in law would gag me and force me to watch as this mans giant hands rubbed my wife’s horny body all over. Sometimes my mother in law would insert her strap on while I was forced to watch.
“You are learning how to be a cuckold husband. And you are doing very well. Soon, you will no longer crave pussy at all. Only my strap on.” She instructed me.
After several months of not fucking my wife, one day while watching my wife get her massage from the stud, she rolled over and took out his gigantic cock and began to suck it. I began to get upset and cried so my mother in law took me away from the door and into the bedroom to listen.
cuckold sex stories
“Now listen to your wife sucking that real man off. Listen to how she moans, and how happy he is making her. I’ want you to lay on your back and stick you legs in the air like a good little sissy slut girl. It will help take the sting out of listening to your wife get her pussy properly fucked by a real man” She said.
I lay on my back submissively as my mother in law mounted me with her strap on. I began to hear my wife whimper and moan as she received that massive cock from her new stud. She was loving it and having multiple orgasms.
“You know he can do a much better job at pleasing your wife than you ever could. Just give into it and be glad that she is being pleased. And focus on how well you are being fucked by me.” My mother in law said.
I began to spurt cum all over my stomach as I listened to my wife climax in the next room.
“That’s a good cuckold sissy slut. Mommy has trained you well. Soon you will be allowed to watch your wife cheating on you as you wife watches you take it in the ass. Then we will all be one happy family.” My mother in law said.
Cuckold Strap On Cross-dressing sex story.
I just found this site. Thanks for the fun stories. I like some of the ideas from “Cuckold Strap On Cross-dressing sex story”. I couldn’t tell who the author is. But, I really enjoyed the animated illustration “strap on cuckold”. That image really made me laugh. Can you tell me the name of the artist? Where can I find more images like that? Keep up the creative writing.
I love what happend!! Her mother in law knew what to do and toke charge and help him be the sissy even if he didnt want that ! Im glad she toke im shopping for panties and sexy outfits he should be wearing and learn his place doing what she told him being used and pimped out to her friends love her mother in law he need to watch his wife getting what she wants and hes a sissy sex slave filmed and told what to do i loved it !
What a shot story, wouldn’t mind that happening to me!!!
Sexy looking mother-in-laws are special huh? Especially when they take control of a guy like the one in this story. One can only imagine what this guy enjoyes and endures once the little wife and her boyfriends are brought into mom’s confidence.
I love that she humiliated him in front of the counter girl when they were shopping.
How embarrassing. 
She should also send him to the drugstore and make him buy female sanitary supplies and stand in a long line to make his/her purchases. And remove some of the price tags so they have to call for a price check on the extra large tampons while he stands there holding up the line.
My clitty is very hard in my panties.
Oh my! I came in my panties twice reading this!
I made my husband into a Cuckold to. He was out of work and losing his self respect while I was working. He is a little man and I suggested that we have wilder sex. I blind folded and bound him and took out my strap on that I bought and he didn’t know about. I forced him to suck it and I mean I forced it into his mouth and told him I would throw his ass out if he didn’t submit to me. That turned him on he had an instant hard on. Then I remended him of how he used to always fuck me in the ass and I said it was time now for me to take over. I rolled him on his stomach loosened his legs seperated them and slowly but firmly inserted my strap on. He resisted at first but gave in right after it got into him and inch or two. I slowly sunk it in all the way. By the time I was done he loved it. He wouldn’t admit it but he was cuming like crazy and so was I. I told this was the way it was going to be from now on. I was in charge. I also told him I wanted to get fucked by other men, real men and I was going to do it even if he didn’t like it. After a few days of me fucking him and him sucking my strap on. I got him some clothes that I wanted him to wear. I got him pink panties,and white lace panties and some teddies. I told him when I came through the door at night he had better be dressed in something that I liked. The first day he wasn’t so I put him over my lap and spanked his ass really hard for him. When he complained I told him if he didn’t like he could get out and I would divorce him. Then I made him get dressed in panties and a bra. I made him suck my strap on for at least and hour then I ordered him to lean over the back of the couch and I fucked him real long and hard. Now that I had him broke in it was time for the next step.
I told him I wanted to get fucked by a couple of big black studs. he wimpered a lot about it,but I told him that just the way it would be and he was going to watch it happen. He really started to complain. We were in route to a hotel where I had a reservation. So I pulled over and made him take his pants down and I spanked him rather hard again. He then said he understood and would obey.
When we got ot he room I told him to strip. Then I gave him a little see threw blue night gown to wear. I told him to get into the closet and stay right there no matter what happened. I ordered him to stay there until I let him come out. I then dressed in my little black dress and took all the other clothes down and locked them in the cars trunk. from there I went to the bar. Where in very little time I picked up not one but two handsome well built marines. One black and the other hispanic. I asked then both up to my room. They both agreed. We weren’t in the room for more than a couple of minutes and I was on my knees in front of the black man sucking his cock he was eated in a chair. I sttod up and dropped my dress off got no my knees again and told the other man to enjoy himself frm behind me. Every one was undressed pretty quiklyand both of them took turns on me doing every thing they wanted. This was my very first double penetration and I loved it. This went on for at least an hour. Then I told them I had a suprise for them. I went to the closet and told my cuckold husband to crawl out. he obediently did. I then told them that he would blow both of them and that they could fuck him all that they wanted. They both had him suck them off and he did a good job. I stood right there and watched. They didn’t really want to fuck him but I promised them that they could finish the night out with me. If they would both fuck him really hard. they riped his night gown off and threw him on the bed and each took a turn on him. When they were done I ordered my husband to sit in the chair and watch as these real men serviced me. As usual he did exactly as ordered. When each man was done with me I told them to have my husband lick their cock and balls clean. They both got a kick out of this.. After they left I ordered my husband to get down on me and lick all of their cum out of me. And finally since my little slut let them rip off his night gown I made him walk nude to the car and ride home the same way.
Can I please be your long distance slave too? Kinda like an pen-pussy?…I’ll do whatever you say. Please? (puppy dog eyes)
I am Missey’s sissy. She ordered me to come here and write about my training. I have to say that I am lucky now to be almost completely trained. It has at times been a long hard road. But now I understand that I can’t please my wife I am not man enough. She needs men that are better than me. When I make mistakes or I don’t obey Missey punishes me. this helps me learn my place.
For instance a couple of months ago I made the mistake of talking when not being spoken to and to top that off Iasked a stupid question. I asked my mistress if I would ever be allowed to fuck her again. She lauffed at me. Which was humiliating all by it’s self. I was completely nude at the time. Which is required of me almost all of the time. She then looked at me in a very sexy way which made me let my guard down. She approached me, softly touched my shouders and then kneed me in my nuts. When I was down she kicked me several times. When I was finally on my feet she then cuffed my hands behind my back. She does this for my own good. So that I don’t make her mad at me by trying to stop my punishment. She then took her hand and squeezed my nut as hard as she could. This hurt so much after being kneed, but I knew that I needed these lessons. She then went around behind me told me to spread my legs and bend over. I thought she was going to fuck me with her largest strap on. She puts me in this position often to do that. But instead I got kicked from behind in my nuts again. While on the floor she positioned me face down legs spread and stepped on my nuts. I couldn’t believe the pain. Then she asked “do you think that I would ever let you fuck me again?” I wimpered that I was sorry for asking and that I never would ask again. I love misey and how she has trained me. She has taken most of my man clothes away from me. I only have enough to go to the store or do things like that. She has me dress almost all the time in womens clothes. Missey likes to get gang banged and my job is to see that the men who are waiting are hard and ready for her. I have to suck their cocks, but I can’t make them cum. I have to have them ready for her. They can fuck me if they wish but I am not suppose to let them cum then either. When these real men are done servicing Missey, I then am ordered to suck any one or all of them off as these real men wish. When they leave my next job is to suck and lick all of their cum out of Misseys ass and pussy.
Missey has in the last few months been fucking her boss at work to, when she gets home she orders me to eat his cum out of her. I have now grown to really like the taste of mens cum.
Missey Part III
As I mentioned before Missey has been fucking her boss while at work and at parties. Also on some buisness trips. Missey works for a company that is unaffected by the econaomic slow down. They still have large parties when they close big deals. The parties are for the employees and their families as well as the clients. misseys boss has a thing for hidden cameras all over the offices. He has a small room off of his office with console for screens he watch every where in the offices from. He doesn’t know that I am a chuckold, he takes great pleasure in fucking Missey at parties and watching me on camera at the same time. He also sits in n office chair and has her suck him off while he watches me on camera. I get a thrill out of this to. Missey alway fills me in on where I was while he was fucking her or she was sucking his cock.
When we get home after the party I always get to lick up his old dried up cum off of Misseys pussy.
The whole time I was reading this I was hot and horne but at the same time wanted to kick his ass and tell him to man up. Good story. The other in-law was just looking out for her daughter
Im a pussy boy that wold love 2 treted the same
I’ll treat you the same. Just for e-mail fun. e-mail me and i’ll have you sucking my cock while you dream of my dick in your mouth… I’ll send you a photo of me first even. I’d like a friend thats into this.
im a pussy boi and want to treated like that, my email is dave70001@hotmail.co.uk
Seriously your all self abusing yourselves be men ,…women only have these fantasies as this is what they want done to them .if your wife wants this then your relationships are over.
Women who treat men like this well you need to end the relationship and marry one of the hunks you fantasize about.
I wish I was a pussy sissy and had a dildo up my little virgin ass pussy
my wife noticed that inserting a finger in my ass while giving me a blowjob made me more erect than she had ever seen before. so she experimented with that and talked me into aggreeing to let her use a vibrator on me. I couldn’t hide my pleasure, although I tried by squirming around and pleading “no! please stop!” but I noticed that the more I whined nd complained, the more turned on she became…
then one day she told me that she wanted me to go with her to an adult wharehouse on the interstate that we passed by once. Thinking that mabye she had some idea of a new sex toy we could have fun with, I agreed emphaticaly! Excited, I went to our new “home way from home” with her. After she pointed out the dark entryway into my new world, I followed her without a clue of what lay in waiting for me.
She directed me into a hallway of doors, pasing by many men waiting in the cooridors. She opened a door marked “vacant” like on a plane. we watched a porno while she sucked my little nub into a stiff pencil with no interuptions. then she pushed a button, and the porno change into two men in a sixty-nine. The views turned me on in the small room until I realized that the volume was so loud! The sound of two men getting off on each other filled the room unexpectedly! Then it happened…..
A man’s penis emerged from a small hole to the right of the video screen. My wife grabbed me by the back of the hed and guided my mouth to the semi hard dick comming thru the wall.
I took it into my mouth like a seasoned sissie, shocking myself. before I knew it, the sides and back of my tounge tasted salty. And I knew that I had a mouth covered in another mans cum!
I looke at my wife and said,”Thats it, I’m a sissie now!
Are you satisfied?
She wasn’t
All day I spent Sucking mens cock and drinking cum!
But she said she had something else in store for my training.
I thiught to myself. Oh no! What have I become?
I made a serch recently on google it returned with a disturbing story on your site that have the author with my name. Is there a way that I can have the name deleted from this site please e mail me back with any information please thank you
I am a young, full breasted Italian girl named Christine (Chris, for short.) if any of you wanna have fun over email, email me anytime at chris.blackwell33@yahoo.com
hi chris i wanna have sum fun