Cross Dressing With My Wife June 21, 2007
Posted by sexstory in Crossdressing Sex Stories, Femdom Sex Stories, Forced to Feminize, Romantic Sex Stories, Sex Stories For Women, Sex Story, Strap On Dildo Stories.trackback
Cross dressing with my wife sex story.
Hi, my name is Timothy and this is the story of how I came to have the best sex of my life, and with my wife of 5 years. It wasn’t always that way, and that is why I have written this story. Perhaps there are other men and women out there struggling with their sex life, as we did.
These are unusual times for married men. Masculinity is on a decline in North America. A man has to go out into the world and be ruthless, cold, and at times, uncaring. He may even be asked to fight and kill other men for his country. Yet when he arrives at his home, he is asked to set aside all of this, and become sensitive, obedient, and thoughtful. It wasn’t always that way, but now it is and if he doesn’t want to lose half of everything he owns, he is expected to conform. It’s gotten to the point, where a man can’t even disagree and argue with his wife.
For most men, the home is a prison. Resentment builds up almost instantly after vows are exchanged. And sex, well sex becomes just as confusing as his role in his own house.
I suffered with all these issues and shortly just figured the best way to deal with it was to work more and be home less. I felt I was trapped. I loved my wife, but it didn’t seem like she understood what life was life for me, as a man, in this world. She had her own agenda as a woman and it was against me. I had to make the sacrifices, not her. It seemed that she should be trying to help make my life easier, rather than making it more difficult. I began not to want to have sex with her because I felt she wasn’t on my side. I didn’t trust her, I suspected she was a selfish bitch and I was stuck with her for life.
The roles of men and women have gone through many changes in North America in a short period of time. What worked for our fathers is now taboo and even illegal. I was raised to be strong and tough by my father, and sensitive and submissive by my mother. My wife was raised to be independent by her mother, and was given anything by her father.
It doesn’t take a detective to spot the train wreck coming.
Sex is the glue to a relationship. I can’t fix the agendas of my society, but I can fix sex with my wife. I can’t change what kind of man I am, or what kind of woman my wife is, but I can change sex.
It occurred to me that perhaps my wife has no clue what it is like to be a man these days. And perhaps I don’t know as much as I think I do about being a woman. So, I thought the best way to learn more is to dress up like a woman, and for my wife to dress up like a man, and to go through a period of time studying the opposite sex.
At first, my wife had do desire to try this experiment. I told her I was miserable and if she didn’t go along with it, than I was leaving her. I actually had to move out for a month and live in a hotel room until she agreed.
Dressing the part. The first step was to go to a mens clothing store and buy a mans suit, tie, and shoes for my wife. She found it kinda cute until she saw the shoes she had to wear. We went to the costume shop and got her a fake mustache and a wig. That night I dressed her up and the result was she looked like a man with feminine features.
Just a note, we live in a world where it’s ok for a woman to wear a business suit but not ok for a man to wear a dress. Tell me that a man does not bear the brunt of this world and I’ll call you a liar.
Because when I went to buy girl clothes, it was quite a different story. It was taboo, I got looks, I felt embarrassed, it was humiliating. My wife picked out a long skirt, smart shoes, matching stockings, panties, a bra, and a blouse. I had my face and arms waxed. OUCH!!! And had extensions to my hair made.
My first lesson at becoming a woman was the discomfort I had in my smart shoes. They were not so smart after all. The bra was hot, and the panties scrunched up my ball sack and cock in a way that was not comfortable. However the feeling of silk wasn’t so bad.
My wife dressed me up as a woman, demonstrated how to apply makeup and tested me to make sure I could do it alone. She picked out matching colors and supervised me cause I could never seem to get it right.
I was surprised at how much I enjoyed my wife’s attention while dressing me as a woman. She was very nurturing and kind and I could tell that she enjoyed it. As I did. It was bringing us closer together and it was good for our relationship already.
The plan was go to our jobs as usual, but after work, I dressed her as a man, and she dressed me as a woman, and we did errands together. Simple things like going to the mall, the grocery store, and even a baseball game once
It was strange to have all the men looking at me. My wife got a big kick out it. I was starting to see how to felt to be an object of desire to every Neanderthal on the planet. It was annoying and I wanted to kick these guys asses. My wife discovered how little anyone ever looked at her and how people were much colder to her on the street and in the shops. I noticed how other woman were looking at me up and down and scoffing about my clothes. Making fun of me behind my back.
What I also discovered was just how expensive it is to keep up your appearance as a women. Makeup, the right clothes, hair appointments, waxing, perfumes, and lotions. It all adds up. My wife discovered how many decisions I made about all kinds of things. From where to eat, and what to do, to driving, and entertaining me for the evening.
It was all an eye opener and a great social experiment. But what we learned most of all, was about sex. After each evening, we would come home and continue to role play. I would put on sexy lingerie and my wife would dress in my tee shirts and jeans. I think it was also her idea to put a large dildo in her pants. I must admit that it turned me on and her too the first time I stroked it in her jeans. She moaned and reached over and fingered my asshole.
Yes, this made me a little excited, and yes it also made me uncomfortable, but after all, the whole thing was my idea and I had to follow it through. One thing led to another and the next thing you know, I was sucking her large strap on dildo. She began to teach me how to suck it correctly and then we would make love while both sucking on it. It was by far the best sex my wife and I had ever had.
Eventually, I knew that I was going to have to take it in the ass. This is not something in our culture that a man does lightly cause once he does, he is labeled a fagot by everyone. It’s not fair, but it’s the way it is.
However, looking back, it was the most valuable thing I learned from this experiment. How a women feels when she is being penetrated. It certainly made me a better lover.
After my wife made me suck her plastic cock, she turned me on my back and lifted my legs into the air.
“I want to see your face as I fuck you in the ass for the first time.” She said.
My cock and balls were completely exposed as she spread my stocking legs and pushed the head of the dildo into my virgin ass. It hurt at first, quite painful really, as she slowly pushed and invaded my butt.
“You have a gorgeous ass and I have always wanted to fuck it, you sexy beast.” She said.
I moaned and cringed and took it like a man. It felt like a giant inside of me and hurt as she slowly and gently fucked me. My prostrate was aroused and I became very hard despite the pain. I felt wonderful to surrender myself to my wife in this way. It seemed to reduce the tension almost immediately in our relationship. Sure, it was a little uncomfortable for me mentally, but the simple truth was that it did feel pretty great.
“I see somebody likes getting fucked in the ass. Don’t deny it, I am looking at your cock and it’s huge.” My wife teased me.
It did feel great, and I came very quickly. My wife kept on fucking me in every position she could think of, and when she was done, she told me she wa going to sleep and I should clean up myself.
Ummm. So that’s what it feels like. Not so good after you have just been violated in a private and sensitive area.
My wife and I began a routine during those months we were role playing. After work, we would dress each other up, go out, come home, and she would fuck me. Then I would fuck her as a man and she was a woman again. It began to blend so much that it was hard to keep track of who was who. And before we realized it, we were fucking 2 and 3 times a day. It was unreal.
Eventually, we only dressed each other up at home. Sometimes we were both dressed as women, and sometimes both dressed as men, it didn’t matter. We were fucking like teenagers and fucking everyday.
So, that is the story of how I came to have the best sex of my life with my wife. I learned a lot about what it’s like to be a woman, and she learned more about what it’s like to be me in this society. We now have more compassion for each other, and can shake off the agendas of our gender with new perspective. Our relationship is by no means perfect, but the glue is there, and the sex is fantastic, and when we have exhausted ourselves, we have forgotten whatever it was that bothered us in the first place.
Crossing dressing with my wife sex story written by Ian Smith.
This was a really wonderful story about the boy crossdressing with his wife. It’s a neat role play idea and I am going to get my husband to read it in hopes that he will allow me to crossdress him, and he can dress me up like a man. It sounds like a lot of fun and very healthy for a relationship.
my wife and I used to masturbate together alot and right away she would say things like what are you doing with your other hand and say I know your playing with your but until I finally would agree with her cuz it seemed that she wanted me to. soon she was wanting to watch me finger my butt. And before long she would say as soon as we got under the covers that I bet your thinking that your getting fucked in theass . I knew that she got off so I would play along . We would take turns telling stories. Hers were always the same . She would say that she fantisize about watching my getting it in the ass by some big dick . Well I mentioned one time that I would like to watch her getting it too. So she imediatly said lets go out and pick up a guy for a threesome and she would tell me that she would let me watch her get fucked if I would let the guy fuck my ass so that she could watch. She would cum so fast if I just talked about it for her. Well one nite I mentioned that the thought of getting it up the ass turned me on and I wanted it it bad but the idea of lying on mey back with my legs wide looking up at some guys face will he banged my ass just didn’t seem right. I said that what if he wanted to kiss me or touch me ,that I just didn’t think that it would work but if I was looking up at something hot like her that it would turn me on and that kissing someone that had the face like hers worked better and that if I could reach up and touch and suck on some tits will I was getting fucked made me so hot. Then I went on to say why don’t we first get her a strap-on and try that first. Well within a day we were at some stores in the city looking for some fun stuff and before you knew it we had decided that we both would dress in stockings ,garters sexy bras and the whole works . soon we had drawers full of corsets , waist cinchers ans all the finest underthings for both of us and she was loving fucking me as much as she could. I loved my new sexy clothes and a good ass poundins as often as I could get it as long as it wasn’t a guy. Well it wasn’t long before I showed her some videos of shemales fucking men women and threesomes with couples. Man that was it. We where looking threw classifieds and picking the hottest chicks with dicks and meeting them at bars and prtending that we where three chicks waniting a good licking and we where off to our room kissing feeling and exploring all we could . We loved it. The best fanticy that we lived out for real was . her fucking my ass while I sucked this chicks dick dry and I liked the one where I was watching her get fucked hard by this shemale while she sucked me dry . I love dressins up and getting it as much as she does and do we get it alot. That god for chicks with dicks.
One of my fantasies was to be fucking a woman, while getting it in the ass…
My greatest sex fantasy is to dress as a complete female while my wife dresses as a man and she becomes my “husband” temporarily. Then “he’ should really pamper the woman in me, dominate me lovingly while making love to me. I like to be penetrated also.
hi, i wanna be a sissy, lip_care01@yahoo.co.in
add me
I loved your story, i’m in london england and dress up in ladies underwear at times. Years ago i went to a fancy dress party where men went as molls and women went as gangsters. It was a bit of a pain with finding a wig to hire and i bought high heels and had my make up done for me. Since then and seperated i started to dress up (as i am now) and love it! i hated the fancy dressing up thing all those years ago. Now i cannot wait to get home and put on my stockings and high heels! Well done you!
I forgot my email address ianhilpus@yahoo.co.uk
Sounds like fun if you can reasonably pass for a female !
wow so much fun i have dressed with my girfriend for the last year or more and have a massive collection of clothes underware and pics of us to any one want to swapp let me know
my email id manor2825@yahoo.com
ZARINA says:
OCt 6th, 2009 at 4:00 pm
i am ZAHEER (ZARINA) a CD from India. I am married for the last 15 years
Its very difficult and tricky situation to reveal your secret that you are a cd to your wife. i told my wife that one of my friends participated in a fancy dress competition conducted by his office staff(it was a fact) and he challanged me that no one could look better than him in a female get up. That part of the story(his challenge to me) was a lie. I told my wife that i took the challenge and i wanted to out do him in makeup and dressing to look like a passable girl. I showed my friend’s picture also to my wife.
My wife laughed at the idea but agreed to take up the challange and we together shopped around buying inner garments, make up items and even a suitable wig. Then one night we started practising. When i married to my wife i started growing a mush as i genuinely wanted to give up cding at that juncure of my life. But then it is a fact that
‘ONCE A CD IS ALWAYS A CD’.
That night i shaved off my mush after many months and my wife started doing the make up on me. At the end of it we both found that i really looked like a beautiful girl. Then the unexpected happened. My wife hugged and kissed me and said i looked great as a girl. I thanked her profusely. We took some pictures and i asked her whether i could remain in that dress for some more time as both of us spend so many days for this day. She happily agreed. She then gave me the name ZARINA to me and called me by the name and asked me how i liked it. I was in cloud nine. The whole night Zarina (me) and my wife were discussing the finer points of make up, dresses etc. Then i removed my dresses(half heartedly) and went for sleep.
Next saturday we received prints of the photos and me and wife sat together and scrutinised the pictures.
she was critically analysing the photos and told me there was still room for improving my make up and to my surprise asked me how about trying it that night again. I was thrilled. That night she made some corrections in my eyebrows and concentrated more on my eye make up. When it was done, i looked really stunning and my wife looked really pleased. She complimented me that i was a very pretty girl. Then we took more photographs which followed by more girlish talk. My wife told me she liked zarina, as with zarina she could talk more female oriented subjects like fashion, makeup, garments etc. My God, what a releief was it for me…that my better half liked the female side of me.
Over the days, she showed great interest in perfecting my makeup, buying more fashionable dresses for me and both of us were very relaxed and enjoying the sessions.
Now Zarina has become part and parcel of our life.
I am not suggesting that you should tell a lie to ur spouse to get it started. But that was what i did . I never hurt her. We are a happy couple with Zarina also contributing to our happiness.
Love,
Zarina.
awesome story, with a truthful slant publish this! -mmm yes
Wow is all I can say.
What a terrific story, which both my wife and I really enjoyed, particularly as we love crossdressing. I say “we” because I love dressing as a woman, and my wife loves dressing as a man. We do it at home at the weekend, but we haven’t yet tried it together in public, although my wife is keen to try.
I keep myself free of bodily hair, so that my nylons, panties, bra etc feel smooth against my skin. My wife helps me with my makeup, although I am becoming more proficient as time goes on. I have several wigs, all of which are shoulder-length or longer, because my wife prefers me to look very feminine. When I am fully made-up, have lovely long hair and am wearing pretty clothes (including silk underwear), I have to say I look like an attractive woman and my wife thinks so too. In addition, I feel feminine and I find I walk more delicately (especially in my high heels) and I behave in a ladylike manner. I can also raise the pitch of my voice to sound more like a woman. My name is Frank, but my wife calls me Francesca.
It is rather more uncommon for a woman to want to dress and act as a man, so I’ll go into a little more detail about my wife’s “gender-bender” activies. In fact, she is even more proficient than I am at becoming the opposite gender. She is actually a rather beautiful blonde, but she has had her long hair cut short so that it is hidden beneath a masculine dark wig. We found an old-fashioned tailor’s shop in a little back street and she brazenly walked in and told the elderly tailor that she was a lesbian (not true!) and that she wanted to wear men’s clothing, so would he be prepared to kit her out? She told me that he looked somewhat surprised for a moment, then said, “Business is business”, and agreed to help her! So he took her measurements and she selected an expensive dark blue cloth, which he said he would make into a classy two piece suit for her, and if they were both pleased with the result, he would make her any other male garments she wished. Fortunately, she is of a slim build and does not have an hour-glass figure, which could have made the tailor’s job very difficult. He explained that, as she did not have (as he phrased it) ” large female assets”, the cut of her suit jacket would disguise her bosom. She laughingly told me of the poor man becoming very embarrassed as he tried to discreetly broach the subject of how one side of the front of men’s trousers is tailored to be larger than the other, to accommodate men’s genitalia, and would she be likely to wear anything that would necessitate such an adjustment. She said yes she would, and he then delicately asked which side she preferred. She replied “left” (she is left-handed, and it was the first thing that came into her mind) and the tailor was about to make the appropriate note on the Customer Sheet he had prepared for her, when he suddenly said “Oh dear, I can hardly write that Madam dresses to the left. I shall have to write that Sir dresses to the left. In that case, I shall require a male name for your Customer Sheet. What shall it be?” My wife considered giving my name, but then she thought that when she dresses as a man, she should have a man’s name. Her name is Carol, so she decided on Charles. Rather than reveal her real surname, she settled on “Smith”. So, my wife has an account under the name of “Charles Smith” with a gentlemen’s tailor! And he agreed that when he contacted her, it would be in the name of Mr Charles Smith. When he phoned our home to advise that the suit was ready for a fitting, I answered the phone, and he actually asked to speak to Mr Charles Smith. I passed the phone to my wife, who said “This is Mr Charles Smith speaking”, and the tailor ended the call by saying “I look forward to seeing you soon, sir.” He presumably said “sir” because there was someone else present in his shop at the time, but my wife adored the fact that he had called her “Sir” and said that I should do the same when she adopted the guise of a man.
In fact, when she visited the shop for her fitting, she remarked how appropriate it seemed that he had addressed her as “Sir” and would he mind continuing to do so? She told me that he had looked perplexed for a moment, then he shrugged his shoulders and said, “Certainly, sir.” The suit needed only minor adjustments and she particularly liked the padding which broadened her shoulders. She wore it at home for the first time with a crisp white (men’s) shirt and a Paisley-pattern silk tie, both of which she bought at the tailor’s shop, with his assistance and advice. He also provided her with a supply of men’s underpants and socks, and she chose several sets of cufflinks. He suggested that the suit would look best if Sir actually dressed to the left while she was wearing it, but he did not pursue that line of conversation! Carol ( sorry, I mean Charles) had ideas about what she would have in her trousers in due course, but for the time being she merely used rolled-up tights. She had already purchased an expensive pair of black leather men’s shoes, with concealed lifts to increase her height, so she was fully dressed as a man. With her dark toupee, and all trace of make-up gone apart from a little black eyeliner rubbed into her chin to give the appearance of “five o’clock shadow”, she looked completely manly from a rear view, but slightly less so from the front, due to her woman’s face. However, she could easily have passed as a delicately-featured man. She examined herself in the mirror and asked me if she looked like a man. I said “Yes” and she turned sharply and said “Yes, sir!” I immediately replied “Yes, sir”, and a slight smile appeared on her face. She came close to me and looked me straight in the eye and said “I don’t need to remind you again, do I, to call me Sir.” “No, sir” I stammered. “My suit fits like a glove” she remarked, “and as you can see, I dress to the left.” I looked down at the slight bulge in her trousers and said “You’re well endowed, sir”. She laughed and said “You’ll see how well endowed I am, but at another time. For now, I rather fancy a smoke, so be a little sweetie and bring me an ashtray”. I was perplexed at this, because my wife doesn’t smoke, but I thought I’d better do as she said. I passed her an ashtray and she reached into the inside pocket of her suit jacket and brought out a brown leather case. She said “The tailor had a case of gentlemen’s accessories, and I rather liked this excellent cigar case. It looks so masculine, don’t you think?” I replied hesitantly “Yes, sir”. She continued “So I stopped in at the tobacconist’s and bought a packet of cigars to fill it”. She opened the case, took out a cigar and returned the case to her jacket inner pocket. “Give me your lighter” she said. I did so, and she placed the cigar between her lips, flicked the lighter and casually lit the cigar. I couldn’t believe my eyes as she puffed on her cigar, tilted her head back and slowly exhaled a plume of smoke. She looked at me and smirked. “A gentleman’s not a gentleman without his, or even her, cigars”.
I hope that gives you a taste of our cross-dressing (and cross-gender) lifestyle. If you like what I’ve related to you, I’ll tell you more.
Wow, Francesca! Your account of mutual crossdressing with your wife is a real turn-on. As a woman, I’m very interested in her cross-gender activities and how she felt, because I’d like to learn more about it before I try it for myself. I’ve often fantasised about being the man during sex and I’ve even mentioned it to my husband, who thinks it’s kinky but hasn’t totally dismissed the idea. Perhaps if he got used to seeing me dressed as a man and behaving like a man, he’d accept it in the bedroom. After all, a woman fucking a man with a strapon is common nowadays. Oh, and I’d like to make him wear frilly lingerie and make-up while I fuck him. Role-reversal is sexy, don’t you think? Please tell me more about you and your wife, especially her.
Best wishes,
Kinksta
Hi, Kinksta, thanks for your message. I hope you succeed in your ambition to do role-reversal and I agree with you that it’s sexy. It’s certainly added a lot of spice to the sex that my wife and I enjoy. If I tell you my wife’s feelings when she “becomes” a man, and some of the problems involved in making her masculine, it may give you some clues as to what you would possibly like to try.
As I’ve said, my wife Carol likes to dress as a man and also behave as if she were a man. I’d better make it clear that she does it for sexual thrills and she has no intention of becoming a man permanently, with surgery or anything like that. When she’s had her thrills, she’s content to return to being a woman again, although there are certain aspects of her “masculine” alter-ego that she retains, such as her assertiveness. She didn’t used to be particularly assertive, but she loves the feeling of power she gets when she’s a “man”, so much so that she now likes to be authoritative all the time. By studying books on the subject, she’s perfected the art of demonstrating authority, and even aggressiveness, through body-language. As she says, nowadays everyone is accustomed to the idea of women with “attitude”, which means women who talk tough and behave tough. So Carol is tough when dealing with people, and she’s found that the tougher she is, the more that everyone gives in to her. She now has absolutely no fears about mixing it with anyone and it especially gives her a thrill when her tough attitude gets the better of men. She freely admits that it turns her on to dominate men, which ironically derives from her experiences of dressing as a man and behaving as a “dominant male”. She’s definitely become the boss in our relationship, whether she’s her normal female self or her alter-ego as a man.
There have been several problems for Carol in being a woman for most of the time and a “man” at home at the weekend, these problems being concerned with her appearance. As I said before, she has had her natural blonde hair cut short so that she can wear a masculine dark toupee. However, some blonde hairs were still visible, for example on her neck, so she has had to dye her own hair black, which now gives a perfect match to her toupee. BUT:- She still wants to be a blonde during the week, so she has several blonde wigs, long enough to cover her dark hair. Naturally, as a “man”, she cannot have long (varnished) fingernails or eyelashes, so she keeps them short and she wears false fingernails and lashes when a feminine appearance is required. For her masculine persona, she has acquired (from a supplier to the acting profession) additional items such as dark sideburns, moustaches, eyebrows and even a make-up substitute for hair on the back of her hands. She’s become expert at applying it all rapidly, so she can transform her prettiness very quickly into a man’s face. Obviously, I know that the “man” is actually my wife but, apart from a slight delicateness of features (which simply makes her look like a youngish man), she looks the part. Furthermore, she has discovered how to lower the tone of her voice and speak slightly louder, to give her voice more resonance. All in all, if you require a young, forceful from-the-hip guy, she’s your man!
There’s an old saying that “Clothes maketh the man” and it’s certainly true with my wife. The kindly old tailor doesn’t bat an eyelid now, when “Mr Charles Smith” phones for an appointment (Carol prefers to see him alone, to discuss her masculine requirements). She has quite an extensive manly wardrobe now, to match any of her moods at the weekend. In addition to several superb shirts and ties that are, quite frankly, better than mine, she has obtained from the tailor a range of excellent suits, sports jackets, casual and formal trousers, splendid gentlemen’s cardigans and waistcoats. One of my favourites is a fine tweed 3-piece suit, which Carol wears with a very nice fob-watch on a silver chain attached to her waistcoat, and I have to say she looks every inch a debonair gentleman as she nonchalantly takes the watch from her waistcoat pocket to check the time. In fact, my wife loves acting the part of a man to the extent that she has developed a taste for some rather masculine pursuits. She made me convert part of an outbuilding into a billiard room, and she had a full-size table installed in it. She arranged to have extensive tuition ( while dressed as a woman!) from a male professional player/coach and she has become an accomplished billiards and snooker player. It has become a Friday evening ritual for Carol to don black waistcoat and trousers, white shirt and black bow-tie, then she challenges me to a frame of snooker. I am considered to be quite a good player, but as Carol’s game has improved with experience, she beats me regularly. In fact, it’s not uncommon for her to rattle off a 50-plus break before I have begun to score. On one occasion, I managed to score only 8 points and my wife then cleared the remaining balls off the table, with a superb break of 132, which is a score I have never come close to achieving. It was thrilling to admire a woman, dressed as a man, playing to such a magnificent standard that she would have defeated most men easily. When I congratulated my conqueror on her mastery of the game, she haughtily replied that, as a gentleman, she owes it to herself to prove to run-of-the-mill men that she is superior!
I have to mention one additional masculine pursuit that Carol has become very fond of, and that is cigar-smoking. I mentioned in my previous account that she had purchased a brown leather cigar-case and had filled it with cigars she had bought from a tobacconist’s shop. Although she’d never been a smoker, she actually lit one of the cigars and smoked it. Actually, she took only a few puffs and then, having demonstrated that she could behave like a man, she extinguished the cigar. She admitted to me later that she hadn’t really enjoyed the taste (her cigar was only cheaply-bought), but she did enjoy the feeling of holding the cigar and the act of smoking it, which made her feel very masculine. She had also looked at herself in the mirror and she adored seeing herself with a cigar between her lips and slowly exhaling cigar smoke. Finally, it thrilled her to see the look of astonished admiration on my face to see her smoking a cigar like a man. So she resolved to incorporate cigar-smoking into her manly activities. Just like her billiard-playing, she didn’t do things by halves. She learned all she could about cigars, and quickly discovered that the cheap one she had smoked was greatly inferior to hand-rolled cigars. She studied different nationalities,types, shapes and sizes of cigars and made copious notes about each brand of cigar’s individual strength/mildness and flavour. She also learned about correct cigar behaviour, such as cutting a cigar, lighting it and ensuring an even burn. She was then ready to visit a specialist cigar shop and sample different cigars before purchasing a selection to bring home (by the way, she visited the cigar shop as a woman, although she made it absolutely clear that the cigars she would choose were for her to smoke). She returned home with several boxes of cigars, an expensive humidor to store them in, and a solid, masculine cigar lighter.
Carol declared that we would dress in separate rooms for dinner that evening (Saturday), because she had a surprise or two in store for me. She instructed me to set the table formally, although I was to prepare salads, to cut down on the cooking. I did as I was told and went off to get ready. I chose a lovely blue dress with a plunging neckline, just showing a tantalising glimpse of my lacy bra. I wore a long, sexy brunette wig with sparkling earrings and necklace and I ensured that my eye make-up, lipstick etc were perfect. Elbow-length gloves and peep-toed shoes completed my look and I chose a lovely, delicate perfume to enhance my femininity. My wife was already waiting in the dining-room and I gasped when I saw her. She stood proud and erect, looking tremendously manly in an army officer’s dress uniform with gold braid and buttons, and a silk sash with a scabbard holding a gold-handled sabre at her side. Her moustache was turned upwards at both ends, giving her an air of bristling authority. She was smoking a long, slim cigar and a row of medals on her chest enhanced her heroic look. She approached me, said “You look ravishing, my dear” and promptly fondled my bottom! I replied “And you look dashing, Sir. But I’m afraid I don’t know your military rank.” My wife haughtily said “It doesn’t matter.Tonight, I want you to address me as Commander.” As I meekly said “Yes, Commander”, she raised her cigar to her lips, took a long draw and calmly puffed her cigar smoke in my face. It made me cough, but she simply placed her cigar in the corner of her mouth and smirked at me. Fortunately, she put the cigar in an ashtray and we settled down to dinner. It was a fabulous role-reversal occasion. In her deep resonant voice, my wife regaled me with tales of her prowess with her sword and her battlefield exploits, while I told her of my admiration for her swordmanship and her bravery (she told me later that she had collected tales from military accounts and novels, but her officer’s uniform had been specially made for her, at considerable cost, by her tailor). At the end of the meal, she escorted me from the table to a sofa, and she seated herself on a leather armchair near me, carefully positioning her sword by her side. She calmly poured herself a brandy, looked at me and said “Only for men, sweetie.” She drank some of her brandy and announced “I need a cigar.” She strode powerfully to the far end of the room and opened her humidor. “This should be perfect” she said as she selected a thick, dark cigar that must have been at least 8 inches long. Returning to her leather armchair, she took a silver cutter from a pocket and carefully clipped the end of the cigar. She then flicked her lighter and gently toasted the end of the cigar, turning it expertly and evenly. When this was done to her satisfaction, she placed the cigar between her lips and puffed slowly, still revolving the cigar slowly. Gradually, the amount of smoke emanating from her mouth increased in intensity until she took one long draw and exhaled. It was a fabulous sight to see my wife, dressed as a military Commander, sitting upright in her leather armchair and looking superbly powerful as she smoked her large cigar! She saw me admiring her and asked “Have my surprises pleased you?” I whispered “More than you could ever know, Commander.”How do I look?”, she asked. I replied “You look masterful, Commander”, which obviously pleased her as she smiled and said “I have one last surprise for you, sweetie. ” She stood up and pointed to a bulge in the left side of the crotch of her trousers. “Unzip my trousers,” she ordered. I did so and she reached down and moved her underpants to reveal a long, thick, flesh-coloured, strap-on penis with a lifelike head. I stood there with my mouth open, gazing at it. “Look at me,” she ordered. My gaze moved to her face, looking in disbelief as she smoked her cigar with evident satisfaction. She slowly and expertly blew a series of cigar smoke rings in my face. “As you have seen,” she said, ” I have a big cock and I intend to use it tonight. Guess who is going to get fucked with it?” “No, please, Commander,” I pleaded, “you can’t use that on a man.” My wife laughed hard and said “As far as I can see, I’m the only man in the room” She clenched her cigar between her teeth, folded her arms and stood with her legs apart and her cock jutting straight towards me.
I’ll tell you what happened next, if you’d like to hear it.
Of course I’d like to hear it, Francesca. I can hardly wait to hear what your wife does to you with her cock. And I loved reading about her dressing and behaving like a man, like her beating you at snooker. I want to be able to challenge my husband at something and beat him, but I’m not sure what, but I’ll think of something. Your wife’s cigar-smoking makes her feel like a man because cigars have always been a guy thing, but she seems to enjoy it so I think I’ll try it myself. My husband will get quite a shock when he sees me smoking a big, fat stogie! One more thing, your stories are fascinating but I don’t think many people see them because they’re hidden in the archives. Why don’t you put them on the current board?
Love,
Kinksta
Perfect!! A very beautiful road to soul a warming climax….gain and again.I love my wife of 5 years to much to admit I’ve cdressed as long as I can remember.I dress on the sly but dream that she’d find out and not care.I prodict we’d be even closer.
I’m sorry I can’t continue my story at present, as I’ve been working away from home for several weeks, under extremely tight time pressures. I’ll post again as soon as I can.
Hi, it’s me, Francesca. I’m back home now and I can continue my account of the evening when my wife cross-dressed as a military Commander and first demonstrated her strap-on to me. As I said, she placed herself in front of me, with her cigar clenched between her teeth, her arms folded, her legs apart and her cock jutting straight towards me. She was leaving me in no doubt that she intended to fuck me with her strap-on. To say I was apprehensive would be an understatement! What happened next….
I was tremendously excited by my wife’s dominance and I secretly wanted her to take me with her strap-on BUT I’d never done anything like that before and I was terrified that it would be so painful as to destroy any pleasure I could derive from being penetrated by my wife. I thought that it was best to say outright how I felt, and to my surprise, Carol (or should I say, the Commander) didn’t sneer or anything like that. Instead, she put down her cigar and put her arms around me, gently fondling my bottom and parting my cheeks. She whispered in my ear that she understood my concern, but I had nothing to worry about because we would take it step by step and she would be gentle with me. She rubbed her strap-on against me and quietly said “My sweet little Francesca, you know you want my cock inside you, and I want to put my cock inside you, so why don’t we make a nice, slow start?” I murmured “Alright, darling” and she pouted and put a finger on my lips and said reprovingly “You really must remember to address me as Commander, because I like it.” I replied “Yes, Commander” and she smiled at me. I helped her take off her scabbard and sash, then her officer’s gleaming boots and her trousers. From a pocket of her military jacket, she produced a black condom and she instructed me to unravel it over the length of her cock. She casually picked up her cigar (which was still at least 6 or 7 inches long) and expertly re-lit it, exhaling her smoke down her nostrils at me, as I knelt obediently before her, rolling the condom over her strap-on. If I’d thought, we could have had a wonderfully surreal photo of a man (dressed as a woman) putting a condom on the imitation penis of a cigar-smoking woman dressed as a masculine military officer, complete with moustache! When I had the condom in place, the Commander suggested that I would become more accustomed to her cock if I caressed it and kissed it. I did so, while she stood still, calmly smoking her cigar, and I have to say I felt so excited and also submissive to my wonderful he-wife. I told her so, and she purred with approval as she pulled me towards her strap-on and gently guided it into my mouth. She told me to “suck her cock” and I willingly filled my mouth with it, licking it feverishly with my tongue. She had me do this for several minutes, then she said “My cock’s nice and wet now, so it’s time to find somewhere else to put it, don’t you agree, sweetie?” I was so enthralled that I could barely whisper “Yes, Commander” as she took me by the arm and led me upstairs to the spare bedroom, where she switched on the comforting glow of the bedside lamp and said that I should get undressed. Meanwhile, in an oh-so-matter-of-fact manner, she picked up a jar of lube and smeared it generously on her strap-on. I was watching, fascinated, when she gently told me that as I was now naked, it was time for me to kneel face down on the bed and put my bottom in the air. She applied copious amounts of lube around the crack in my cheeks, then used her fingers to insert even more into my hole. Her probing wasn’t particularly pleasurable, but not too uncomfortable either and I found that I was losing my fear as excitement took over. My darling wife’s tender treatment of me was reassuring and I was actually beginning to look forward to her mounting me. She got me into a position, over the side of the bed, that was the right height for her and told me to stay still while she went to the bathroom to wash the excess lube off her hands. When she returned, she re-lit her cigar and stood behind me, quietly smoking. From my position, all I could see was a blue haze as she exhaled her cigar smoke. Then she calmly announced “I’m going to fuck you now, Francesca. Are you ready for my cock?” I hoarsely replied “I’m ready, Commander” and I began to feel my wife’s strap-on probing the crack in my cheeks.
To be continued….
Francesca here again. I’m sorry I had to end my previous message so abruptly, but I suddenly caught a whiff of cigar smoke, which could only be my beautiful wife’s cigar smoke and I suspected that she was coming to fuck me (I was correct!), so I’d better stop typing. Anyway, she’s had her way with me (which I’ll tell you about, some other time), so I can continue with my account of the first time she fucked me….
Her strap-on was touching my bottom and I just remained perfectly still, listening to her soothing words: “Relax, my sweet angel. You have such a lovely little pussy, and my cock wants to caress it. Just relax.” I liked how she had referred to my ass as my “pussy” and I loved how she called her strap-on her “cock”. I did relax and she gently guided the tip of her cock into my ass. She kept asking if I was OK, as she ever-so-slowly penetrated me even further. She frequently stopped to allow me to become accustomed to having something up my ass, and she occasionally withdrew to apply more lubricant. Each time she re-entered me, her cock slipped in more easily and I discovered that each re-entry was relatively free from discomfort. Only when she ventured further into my ass did it cause me to flinch, but she proceeded agonisingly slowly to ensure that she did not really hurt me. I lost all track of time as I relaxed, enjoying the fact that my lovely wife was fucking me, but doing it in such a caring, loving way. It must have been ages later that I sensed a change in her routine: instead of always withdrawing completely, she began to partly retract her cock, then slowly move it forward again. It dawned on me that she was actually riding me, and it thrilled me. I told her so, and she purred with satisfaction. I experienced the sensual pleasure of her cock touching my prostate gland, and she heard me let out a little gasp. I explained what was happening and she told me to relax and enjoy it. As she penetrated further, I began to feel randy and I asked whether she would allow me to hold my penis. I adored how she replied, with a slight laugh in her voice, “Of course you can, sweetie. Why don’t you have a nice wank while I’m fucking you?” I grasped my penis and started moving my hand up and down the shaft, feeling more and more horny as my wife toyed with my insides. As my masturbating became faster, she responded by increasing the frequency and strength of her thrusts. I gasped to her that I was going to cum, and she told me to do it. Fortunately, she had prepared for this by placing a large towel over the bed, which was just as well because I exploded, spurting semen all over the towel. By this time, my wife was riding me hard, but if there was any discomfort I didn’t feel it. When I had spent myself, she stopped riding me and kept her cock motionless inside me. She asked me if I wanted her to withdraw, but I said no, I wanted her to fuck me some more. She started again, not thrusting but gradually penetrating even deeper, and she told me to keep my hand off my penis. I felt her grasp my hips as she pushed her cock steadily further into me and I heard her say “Good girl” to me as I began to push back against her. I wanted to stroke my penis again, but she refused me permission, saying that she would be in charge from then on. I could feel discomfort now as she thrust into me, but all I wanted was to masturbate some more. I couldn’t help myself getting aroused again and apologised for approaching another orgasm, when to my surprise, she reached forward, grabbed my penis and wanked me in rhythm with her thrusts. As she sensed me cumming, she banged her cock right into me and I screamed from the pain mixed with the ecstasy of ejaculating another load of cum. This time, she did withdraw fully and let me flop on the bed. I lay there with a sore ass, sore insides and an over-sensitive penis that I could barely touch, but I had experienced the most fantastic sex ever. I looked lovingly at my wife as she calmly cleaned her cock with the towel, propped a pillow against the headboard of the bed, sat back against it and casually took her cigar from the ashtray and flicked her lighter. She took a deep draw on the cigar and I watched admiringly as she let a large ball of smoke escape from her mouth. It seemed to hang motionless, then it disappeared up her nose as she expertly french-inhaled. She tilted her head back and satisfyingly exhaled a thin plume of smoke into the air. As I’ve said before, when she puts her mind to something, she can soon become very good at it. She had quickly become an expert cigar smoker and I knew that she would rapidly become a master of strap-on sex. I giggled and pointed to her still-erect cock pointing upwards from between her legs. She smoked her cigar deeply, turned her head towards me and slowly puffed a thick cloud of smoke into my face. “Do you like my cock?” she asked. “I adore it, darling” I replied. Her eyes blazed and she said “What did you call me?” I was shaken by her sudden display of power as I hastily stammered “I’m sorry. I meant to say Commander.” “Don’t make that mistake again, you fucking bitch”, she said sternly, adding “I can of course call you bitch now, as I made you my bitch when I fucked you.” She continued, “I’m glad you adore my cock because you’ll be seeing and feeling a lot more of it from now on. By the way, I like the idea of a woman’s cock being bigger than her husband’s and it surely won’t have escaped your attention that my cock is bigger than yours, AND my cock doesn’t go soft like yours. No matter how often or how long I fuck, I have an erection. So I reckon I’m more manly than you.” She clenched her cigar in the corner of her mouth, leant forward and looked me straight in the eye. “So we’ll have me as the man more often, and naturally I’ll expect you to be the perfect woman for me to fuck. Got it?” She forcefully blew cigar smoke in my face as she impatiently awaited my reaction. “Yes, Commander”, was all I could think of to say.
To be continued….
Sorry for having to interrupt the story again, but I realised I was rapidly running out of time to get on with some work I really HAD to complete. Anyway, I thought I’d better relate the finale of the special occasion when my fabulous wife Carol first fucked me….
I had been quite taken aback at how suddenly her loving, caring sex with me had turned into a tirade from her. When we’d relaxed for a while, I hesitatingly asked her what I had done wrong. She had calmed down by then, and she actually apologised, saying that she had felt somewhat resentful that her considerate love-making had made my first strap-on fucking so good for me and had given me two great orgasms, but she had been unable to enjoy herself as much as she had hoped she would, because she had stopped to prevent the experience becoming too much for me and leaving a strongly negative impression on me. So, in other words, she was feeling sexually unfulfilled, while I had enjoyed myself enormously! I gently told her how much I appreciated how skilfully and lovingly she had penetrated me and fucked me, how much her love-making had turned me on and that I wanted her to fuck me again and again in future. I added that I would never stop wanting to be her bitch and having her drilling me as hard and as often as she wanted. I ended by whispering in her ear that I admired and adored her big cock and there was no contest between her and me that she was the “hard man” in our house. Finally. I moved down the bed, kissed her strap-on penis, looked adoringly up at her and said ” I’ll run a warm relaxing bath for you, clean your cock thoroughly, select some of your gentlemen’s clothes to relax in afterwards, and bring you a nice drink.” She seemed pleased with this, so I arranged everything for her as I had promised. I tidied my hair and re-applied my make-up and feminine clothing, adding an extra touch of perfume to make me smell nice for her (and possibly get her aroused again!). When she had finished bathing, I towelled her dry and helped her into her gentleman’s outfit of discreetly-checked shirt, cotton underwear, smart flannels with a razor-sharp crease, comfortable shoes and, as a final touch, a paisley-pattern cravat. As she was about to sit down, I said “Allow me, sir”, unbuttoned her flies and inserted some packing into her underpants. She said “That’s very thoughtful of you, Francesca”, as I adjusted her bulge to her preferred left side of her crotch. She had dispensed with her moustache, but had applied neatly-trimmed sideburns to complement her “clean-shaven” face. She had no wig, only her own short hair, and her look was that of my wife dressed as a man, and I have to say she looked suave and debonair. I poured her a whisky and soda, while she opened her humidor and selected one of her cigars, a medium brown slim panatella. She carefully lit her cigar, settled down in her leather armchair, took a satisfying drink of her whisky and raised her cigar to her lips. I looked at my wonderful wife and thought admiringly how much she gave off an aura of calm control and authority. She was smoking her cigar powerfully and confidently, looking for all the world as if it were the most natural thing in the world for an attractive young woman to smoke a strong cigar and dress as a man. She exhaled jets of cigar smoke down her nose and said ” I rather fancy that I’ll fuck you again tomorrow evening, Francesca, my lovely bitch-husband. Now that I’ve broken you in, I’ll fuck you a little bit harder and see how you take it. All right?” The abruptness and certainty of her statement thrilled me. Once again, all I could think of to say to her was “Yes, sir.”
The following evening, while we were quietly watching television, my lovely wife Carol announced that she was ready for a good hard fuck. By that, she meant that she was ready to fuck me hard with her strap-on penis. She ordered me to go upstairs and make myself pretty for her, and stay there until she summoned me. When she did so, I was surprised to see that, although she had dressed as a man (once again, I was thrilled to see, in her officer’s military uniform), she had made her head look very feminine. She had applied the most lovely make-up, including long eyelashes and gorgeously shiny lip gloss, and she was wearing a long, silky blonde wig which cascaded over the epaulettes of her broad-shouldered uniform jacket. She noticed the surprised expression on my face, smiled and informed me that she was enjoying a variation on her gender-bender activities: she was being part-man, part-woman. Besides, she continued, why shouldn’t there be a beautiful woman Commander, particularly when she is more manly than the men she commands. As she said that, she pointed to the bulge in her trousers, which seemed to be straining to break free (she must have positioned her strap-on horizontally, to make it seem even bigger than on the previous evening). She complimented me on how ravishing I looked as a woman, and said how much she was looking forward to fucking me, then she took my arm and escorted me to the bedroom. As before, she produced a wicked black condom and ordered me to unravel it over her cock, then she turned to admire herself in the mirror and began to run her hand up and down her cock, as if she was wanking slowly. She then stopped and took a long, thick cigar from her uniform inside pocket, meticulously going through her ritual of cutting and lighting the cigar, before pausing for a short time to admire herself in the mirror as she smoked. When she turned round to look at me, I gasped at the sight of this beautiful blonde woman looking so magnificent, with a powerful dark cigar between her glossy lips, and her feminine face and hair contrasting with her masculine uniform and sword, and finally her black-condomed cock jutting menacingly at me. She commanded me to apply the lubricant to her cock, then take off my knickers, hitch up my dress and put plenty of lube on my “pussy” (i.e. my ass crack). Then, she ordered me to lie on my back, with my legs in the air, because she wanted to see my face as her cock penetrated me. When it did, I let out a gasp, and she smiled wickedly. She wasted little time in entering further into me, which was not wholly pleasurable for me, but I had received my pleasure the previous evening and now it was time for the Commander to enjoy herself. As she thrust into me, she leaned forward threateningly, her powerful cigar clenched between her teeth. The tip of her cigar was so close to my face that I could see it glow and feel the heat as she drew the strong smoke into her mouth, and I could see the look of triumph on her face as she exhaled her smoke over me and continued ramming her large cock into me. I orgasmed, shooting semen over my stomach and chest, but I don’t think the Commander even noticed, so intent was she on fucking me hard. She ground her crotch against me and the base of her cock, becoming more and more frantic, enveloping both of us in her cigar smoke as she climaxed with such power that she thrashed wildly on top of me. She looked briefly at me, said “Give me more, you fucking bitch” and started ravishing me again. She had four more climaxes before she finally stopped, leaving me feeling sore and well-used, as well as covered in ash from her cigar, which she had not once removed from her mouth while she was fucking me. She withdrew from me, breathing heavily and saying that I was the best fuck-toy in the world. At least I’d pleased her!
I’ll tell you next how our sex lives have developed since these first two occasions that my wife fucked me….
Final instalment for the time being….
My gorgeous wife Carol derived so much pleasure from the first two occasions that she dressed as a man and fucked me with her strap-on penis (especially on the second occasion) that she wants us to do role-reversal as often as possible. However, we both appreciate that it takes a long time for me to apply my make-up perfectly, and for Carol to alter her face and hair with moustache, sideburns, toupee etc. We’ve decided to save these time-consuming (but tremendously satisfying) procedures for occasions when we have plenty of time to get ourselves looking “just so”, and we can leave the clearing up until the following morning. So, it makes sense to have these full-blown “drag and pegging” sessions on Friday and/or Saturday evenings, when neither of us has to go to work the following day and we can therefore have a lie-in (which I certainly need after Carol has fucked me hard for ages) before tidying up and returning everything to normal. However, Carol has a high sex-drive and she usually fancies several bouts of fucking during the week as well, so we’ve devised a strategy to accommodate her urges. Some evenings, we’ll just have normal husband/wife sex, which requires nothing more than us being naked in bed. When she wants to be the man, we simply cross-dress without altering our face/hair genders. So, I’ll dress in women’s clothes but still have my normal masculine face and hair; Carol dresses in some of her manly clothes, but retains her long hair and feminine face, complete with make-up, long lashes, perfume etc. After all, her face and hair were beautifully feminine when she was dressed as a military officer on the second occasion she fucked me, and it certainly didn’t spoil our pleasure, far from it. To tell the truth, I prefer her to have feminine features when she dresses as a man, because it’s terrifically thrilling to me to see my wife looking feminine but dressing and behaving in a dominant, masculine manner (especially when she produces her “cock” from her trousers and fucks me with it!) It does give Carol an extra thrill when she goes the whole way and adorns herself with her moustache, sideburns etc, and she does like seeing me in make-up, because it reinforces the scenario that she’s the real man of the house, but I think she’s gradually becoming more turned-on by the idea that she’s a beautiful woman whose head looks utterly feminine, but her persona is that of a suavely dressed, masculine, powerful man. I think this is the direction we’re heading, with both of us being part woman and part man. It’s just that I will be more feminine and my wife will be more masculine. It may sound confusing, but our role-reversal is hugely exciting sexually for both of us and it’s a natural extension of our both being turned-on by Carol’s dominance.
There is one final thing I’d like to mention, which sounds totally unbelievable, but is true…..
I started my post dated July 15th by saying that I could smell cigar smoke, which could only be my beautiful wife’s cigar smoke, and it was likely that she was coming to fuck me, which is what she did. That probably seemed an odd thing to say, but it is a fact that Carol feels incredibly butch when she smokes a cigar, so much so that she invariably wants to don her strap-on penis and fuck me. So, to avoid her fucking me every moment of every evening, and also to cut down on the not-inconsiderable expense of her cigar-smoking (her cigars are wonderful but expensive), we agreed that she would only smoke a cigar when she planned to fuck me. Therefore, when I said that I could smell her cigar smoke, I guessed she was going to have her way with me, and so it proved. But there have gradually become more occasions when she likes to dress as a man in the evening without having any intention of fucking me, and she fancies a smoke, so what could she do? She won’t touch cigarettes, which she says are so sickly after the exquisite flavour of her cigars, so what else would she smoke as a man? Yes, believe it or not, she learned all about pipe-smoking and she bought several pipes and many different types of tobacco, which she is experimenting with to discover her favourite combinations. As I said, she’ll happily sit in her leather armchair, dressed as a man and quietly smoking one of her pipes. And if you think that’s unusual, I said that she likes to simply be a woman much of the time, so it’s now completely normal for her to sit, dressed in her feminine clothes, reading a book while puffing gently on her pipe. As I knew she would, she’s quickly become an expert pipe-smoker, playing delicately with the smoke in her mouth and exhaling beautifully. She loves it, and I’m thrilled at the sight of such a beautiful, feminine woman smoking a pipe so sexily.
Kinksta, and everyone else, I hope you’ve enjoyed my accounts of Carol and me. Please feel free to comment if you so wish.
Love,
Frank (aka Francesca)