Crossdressing with my wife

Recently I put in my wife’s panties to see her reaction when she woke up and saw me in them. She got horny and loved it, she giggled and took pics. I’ve done it more and the last 2 times I wore one of her skirts and last time wore a bra. How do I get my wife to want me to dress even more? What I mean is I wanna wear makeup, shave everything and wear a wig and have that turn her on too, but I don’t wanna go too fast and freak her out. How do I progress this or find out how much she likes (hopefully all the way) til I end up completely dolled up with her? I really really want to have sex with my wife dressed like a hot woman, fake boobs and everything if I could just find out how

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  • Darling your post has started to get a fair way off the original subject but still interesting anyhow how are you going sweetie.
    I know you both will just adore lingerie and cross dressing with make up and everything feminine for you.
    Love you both enjoy xxxx

  • Everything has been perfect. Our love for each other has never been stronger and she’s really into it too. She even suggested we go to a comicon out of town later this year and I dress as Princess Leia for her. I am SO thankful for your advice, you’ve helped me make us happier and more open with each other about everything ;)

  • OH Darling you have brought tears to my eyes, this is such the greatest outcome, I have just finished making my husband up he looks so nice, I got him a Latex catsuit with thigh high shiny boots/black heels he does not want to get out of them and I can't stop touching him cuddling and feeling, a bit expensive but very much worth it, he spends hours shinning and cleaning them after use and they have pride of place in our wardrobe now.
    I just was so certain you would be accepted by your wonderful wife, bet you cannot wait to get out in the open all dressed and made up that is one thing we have not done, we have married friends where the husbands cross dress and about once a month go to each others homes, males all femme for an evening meal, so great, the home owner dresses as a French Maid, cooks, serves and all the gurl's wash and clean up.
    Love you Darling xxxxx

  • That sounds like fun too ;) If only other people knew what they were missing out on. They were prob like me and thought they were of the few, had I not told her we would have still been very happy. It’s just that telling her both increased our love for each other and made me very happy being accepted for something I hid from everyone my entire life.

  • Thank you Darling your such a sweetie, you have inspired me to start thinking when I am going to get my husband all Femme and out in the open we have talked about it a couple of times but now I am so very keen to do it, we have a large town not too far away so I think we will book into a hotel there drive over with hubby dressed and made up book in then go to a plaza purchase some new lingerie for him and have a nice meal together, we should be very horny when we get back to the hotel. Next morning I will get him dressed and made up go for a long breakfast and then drive home xxxxx

  • I love the idea! You’re going to have an amazing time, I hope to hear about it someday how it went!

  • We had a bit of a turn at it today just driving around town we stopped at a park and sat outside having a coffee, I dressed him in a sexy hot pink pantie and padded bra set, suspenders, stockings, heels, peach almost see through blouse and short leather mini, very nice makeup with lashes and a curly, blond long wig, he looked so wonderful and so very sexy.
    It went so well he just didn't want to come home I am so very happy he really looked like a girl we are so lucky that when slack his cock and balls form a nice tight bundle so he can easily wear off the rack lingerie although he does have a couple of gaffs that pull him right up if necessary, he is getting OK with his heels but does need a lot more practice out of the house.
    So glad he is now so confident, I really hope you are going great and sure your wife is also loving you being so happy, keep up the good work Honey.
    We have decided to ask another couple to accompany us next weekend getting the guys out dressed will be fantastic xxxxx

  • He is obsessed now about getting dressed femme and going out in public we did it again this morning to have coffee and breakfast near the park there were a lot of people around and he sat with legs partly open so a few could see his sexy red panties, I am certain noone suspected he was a cross dresser.
    On the way home we went to the adult store and purchased a double ended strapon dildo, he has a bit of a sore bum at the moment but we both loved it, I lubed him well and he got into the doggie position it took a while to ease his end in, he moaned while I started riding him but liked it after just a short time, maybe you should try that Darlin xxxxx

  • That sounds like you had an amazing time. I wish I could be hot enough so people think I was a woman too. So do you pick out what he wears when you go out?

  • Confidence Darling, your just starting out whereas we have been doing it for a long time although only just now started getting him into the outdoors, he really loves it, I feel it is so very important, we have perfected his makeup, walk and general female attitude he looks great, the other guys are keen to start trying it as well, we shop together now when we go out and he uses the female toilets, we loved going to the adult shop and picking out the strapon with the help of a female assistant he really loves me doing him doggie style can't get enough of it although his bum still gets quite sore I am sure he will stretch into it soon, I never knew how I would adore being so dominant, I have started talking about getting a cock cage for "my gurl" so I would be in total control he is not sure but I put my foot down so we are getting one next Saturday.
    Really hope your first outing turns out well I am certain it will darling you will look so nice as the Princess. HEY ! do you think your wife would like to start pegging you ? I never thought my gurl would like it but she is addicted xxxxxx

  • Thank you! I really hope I do look good. Over the last week my wife and I went shopping and she helped me pick out some dresses and cosmetics and tonight she did my makeup for me. I’m wearing my black cocktail dress she helped me with and this is the first time I’ve ‘put it all together’ and I just have his feeling. I don’t know how to describe it, I’m like completely feminized right now and it’s amazing sharing it with her. It’s kinda a tingly feeling and I’ve had it all night. Then reading all this makes me

    I’m not sure how I’d bring up pegging. Now you got me thinking about it, Mandy like dominating me would be so hot like that, does it feel good too?

    I’d really like to continue chatting with you, you should email me. I’ll sift through the spam I’m going to get here until I find you. I’m not looking for anything, I just like talking to you and if you feel the same maybe we could chat there. Anyway it’s

  • Thank you Mark I really love the way you are advancing and obviously really enjoying it, it is so great to hear your wife is so supportive, just start talking to her about the pegging, having her peg you will be just so great, you will need to lube up quite a bit and best to start wearing a butt plug around the same size as the strapon dildo you intend to use she can also start fingering your bum as much as possible, she will have to be patient putting the dildo in for the first few times and you may get a sore bum but sweetie it will be well worth it, I suggest you start off with you in the missionary position with your legs real high she will access quite easily then when you are both happy start the doggie position you will both adore that.
    Today we purchased the cock cage a clear plastic with internal locking devise designed for lengthy wear and my gurl is locked now so I have completed the domination, not too sure when I am going to let her orgasm but I have cuffs and leg spreader for when she needs to be released for shaving and cleaning plus I will tease her to precum before locking again, if she brings up the subject I it will just take a lot longer before I allow her to orgasm, I am going to peg her later this afternoon first time caged.
    I would really love to e-mail you darling but I am concerned about doing that so lets just stay on this post for a while EH ?
    Really, really like you Mark xxxxx

  • I guess I don’t know how to bring it up with her. I don’t want it to be too much too fast but if there was a way to make it her idea then it’d probably work. It sounds like you two have an amazing time with it, I hope someday to have some wonderful stories like you. What’s it like to be caged? If it’s days and you tease her to precum, when you finally let her orgasm what’s that like? Every day you seem to have something new and hot, you’re spouse is very lucky!

  • Thank you Mark just take it slow Darling don't rush enjoy every advancement ensure you encourage and thank your wife at every opportunity, I am certain things will move a bit quicker after you go out in public I think that is just so important we are getting very comfortable going out with my gurl dressed and Femme now it took years, she loves me being in control, she is just so sweet, obedient/attentive, she has only started being locked in the cage today while she will be released for shaving/cleaning and teasing every Sunday she will not orgasm for quite a while I am not too sure how or when I will let her orgasm just yet, this afternoon I pegged her with the cage on and it was great for me those double ended strapon dildo's hit my spot when I do her doggie, she could not get a horn the cage holds her lovely and tight pulling hard on her balls if her pussy tries to lengthen or thicken but she did have some precum, her bum is just a little sore she is getting very used to it.
    Please just talk a lot and be nice to your wife but don't push things love I am sure you both will adore her pegging you and certain chastity will happen sooner or later you will love it Darling.
    Outside our fetish life no one knows what is happening, that is the good thing about it.
    Love you xxxxx

  • Hi Mark, this morning she desperately tried to have her usual roaring erection but the cage soon put an end to that, I did not help the situation playing with her ovaries and nipples ( she no longer has a penis or testicles they are known as pussie and ovaries while her breasts are titties ) she loves those words.
    Eventually after fingering and lubing her bum I decided to peg her, she got down on all fours on the thick fluffy lounge mat and took it very well I came three times before I had her clean me out, she had a fair quantity of precum.
    Her bum did not hurt at all today however she did have painful ovaries probably what we used to call lovers balls, I am sure her pussie will soon stop trying to enlarge while caged.
    Today she is getting dressed in her latex catsuit and thigh high boots we are going to try and find a secluded place for her to have a while in the outdoors she really looks and feels spunky in that outfit.
    We are having Pam and Bob over for dinner we are going away with them next weekend so they will be the first to see her pussie caged hopefully Pam will insist Bob goes into chastity as well. Mark it is so wonderful I really love the dominant feeling and she likes it a lot, well I don't get any complaint's and she does not bring the subject up anymore.
    Hope you are progressing well Darling, I think you should start talking about being pegged first then when you are both comfortable try the chastity your wife will go for both. Love xxxxx

  • So there are double sided ones you can get pegged with? I might be able to get her to go for that, where could I get one? I’m not sure if that’s a strap on or not. Chastity sounds hot too but what’s in it for women? I’m just trying to make sense of it first so I know how to go about it with my wife.

  • Darling just go to your local adult store they will be most helpful, we purchased the leather holder and the dildo separate the double ended gives both the gurl and dominatrix a really great thrill going into each others hole obviously the dominatrix is fully in control, it does not take long to know the rhythm that best suits for orgasm but my gurl does not have one while caged.
    As for the cage it gives the dominatrix absolute power I adore that the locked gurl is under my control, not to say they don't like it she has become very subordinate, obedient and caring really loving me being in charge while she is dressed.
    We had a nice trip today not far away with a picnic in the woods, secluded so she could walk around feeling and looking so very sexy.
    There are quite a few sites if you google "chastity" and "pegging" you would be astounded at the information and the amount of people that participate.
    Got to go Darling Pam and Bob will be here soon so I have to make sure she is perfect for them, I have a lot of information on chastity for them, I really feel they will take it up.
    Love xxxxx

  • How good is this Darling, Pam was very excited about my gurl's cage and is going to purchase a pink one this week, we are going to have a little ceremony next Saturday to lock it onto Bob's pussie, I have agreed to let them watch me peg my gurl after that, Pam sort of indicated privately she might like us having a play together with the double dildo, could be great fun I have had a few lesbian relationships in the past and feel I need to revisit that sexuality xxxxx

  • That’s awesome! If you two end up having a go at it, are you going to make your gurls go at it too? Maybe that’s going too fast that quickly but if you and Pam end up all over each other, watching the gurls go at it could be very sexy. I hope your next night together is amazing, I so wish I could experience all this right now! I just got back from a short drive wearing my black dress, my high heels and some makeup, it was the first time I’ve ever left my home like this. I guess I’m a ways back lol but that was huge for me. I do love hearing everything from your perspective; your stories, your tips and especially your advice. It’s too bad we aren’t like neighbors, you seem like great people and you’re much more interesting than my friends ;)

  • OH no Mark, no,no,no the gurls would never be allowed or even want to play with men how horrible.
    Just take your time and go slowly with your transformation, enjoy every step, your wife should be starting to take more control and be eager to assist, my gurl is always Femme now when not at work it is so good she is so happy, she always wears sexy panties and at least a training bra now even if in male gear, her pussie is still trying to get hard in the morning but she is learning quickly it is just not on so soon that will cease, I play with her ovaries, bum and peg her each morning now.
    Pam has asked if we could send the gurls shopping for a few hours this weekend so we can have time alone to play, I am getting quite excited and have told my gurl what is happening she is very happy for me.
    We will have such an action packed wonderful weekend.
    Keep up the good work Darling it should not be too long before you are Femme most of the time as well, I am so happy you are getting more confident being outside dressed it is good isn't it ?
    Love you Darling xxxxx maybe tonight a little whisper about pegging eh ?

  • I can’t describe the feeling I had doing that last night. I was so scared and nervous, I can’t believe I actually pushed myself to do it and it was so hot omg. I will bring up pegging soon, maybe this weekend with her. Will you and Pam do any pegging?

  • Darling that is very normal it took a few years before we were open to contact with friends that liked partners cross dressing and only in our houses just take things easy and ensure your wife is part of the adventure, I love pegging my gurl but when Pam and I are together this weekend I know we will fuck lesbian style using the strapon and 69er and just playing I am sure you can imagine, it has been a while but Darling I can certainly bring it back.
    Looking forward to such a great weekend, Love you xxxxx

  • Have fun ;)

  • Thank you Mark, Bob and Pam had today off getting ready for our weekend away while my gurl and I had half a day off, we are all ready and waiting for them to pick us up we decided to stay another night, the gurls are wearing slacks, pantyhose, and sexy lingerie (padded bras) with light almost see through floral blouses for travelling, Bob is a brunette and my gurl is blond she looks very pretty, tonight everyone will get dressed very sexy for a nice seafood evening meal, we have booked a discreet window corner table and insist that the gurls have to do all the talking to staff just a bit of humiliation but mainly for confidence.
    Tomorrow prior to breakfast we are going to have Bob's shaving and locking ceremony then after we are sending the gurls to town for at least four hours so Pam and I can begin our lesbian relationship.
    We are booked for a show with three course meal tomorrow night so it will be evening wear for everybody.
    Just can't wait they must be here soon, love you Darling keep up the good work xxxxx

  • Finally found an email with this link, I’ll have to save it and not lose it this time. Anyway hope all is well, I hope your lesbian relationship is going well!

  • I have the opposite problem I want my husband to feminise and cross dress because he is far too much the man and I am sure it will help quieten him down and make him more responsible, he has been quite resistant but I have been very firm, first I started by not letting him have any nooky unless he had my panties on then I purchased 3 matching pantie and bra sets and 6 panties removing his male underwear altogether again no nooky unless he wore panties all the time and put on a bra at home next I started with lipstick mascara and some blush every afternoon after he showered I watched and helped him shave all over giving him a blow job for being a good boy, this weekend we are going to the lingerie store to purchase more pantie and bra sets along with suspenders and stockings then for a nice pair of heels, after he gets used to wearing heels I am getting him a nice wig, things are happening slowly but they are happening every time I progress I don't go backwards but continue to move him to my next goal.
    Soon I will be taking photo's of him showing his female side and keeping them in a real safe place, not long and I will have a nice obedient gurl.
    Please feel free to suggest a sexy female name for her.

  • Tuls would be great, are you making him a Sissy and how far do you intend going ?

  • That was not my initial intention but because he has been resisting feminisation at every opportunity he is going to be taught a real good lesson I have purchased a leg spreader cuffs and a cock cage next time I am shaving him I am going to fasten the leg spreader then cuff him I want to see the look on his face when I bring out the cock cage, once locked on I am going to hide the keys before letting his hands and legs free.
    He will certainly squeal and carry on but he will be informed that will be taken into consideration for the time of lockup he will soon quieten down and do exactly as he is told, I am going to have a very obedient little Sissy from then on.
    I did not instantly get Tuls as his name but do now that is wonderful so be it I might even get it tattooed on his butt

  • I wish my wife was just like that with me. I think Zarah would be a hot name

  • Thank's Sweetie it's Tuls more appropriate "do you get it" ?
    I hope your wife gives you a great dose of dominance just like you wish for xxx

  • Good on you girl once you get that cage on him he will certainly change his tune and atitude, you just stay firm and you will have a wonderful obedient gurl
    Ensure when he is shaved and cleaned he remains cuffed behind and with the spreader on tease him to precum but don't let him orgasm

  • Thank you everyone, you were all so helpful especially the lady who first gave me advice. Yesterday I decided to buy a pair of black lace panties and wear them for her, Ive worn hers before and she uses that as a signal for sex. But today when I showed her, she smiled widely like she usually does but then asked where I got them. I thought ‘oh shit’ and danced around the question but she said she knew they weren’t hers because she doesn’t like lace. She said she liked that I went out and bought them and asked if this was the first time and she could tell by looking at me that it wasn’t and she started asking questions and I answered honestly. I told her everything, and she was as open and supportive as I could only have dreamed. I told her how I started when I was 6 and she was very surprised but the more I told her the more she seemed to like what I was telling her. I showed her pics I had taken of me wearing numerous dresses of hers, panties, lingerie, etc. She also said it would be fun to go out and buy some stuff for me and would like seeing me all dolled up, makeup and all. Never in my wildest dreams did I ever expect such a positive, supportive response from her as she gave me, I’m still floored how open and excited she was when I told her, thank you all for he amazing advice! I am so happy! Thank you all!

  • That lady is me Darling and I am over the moon happy for you, what progress, you must have a wonderful wife.
    Both of you will start noticing subtle changes in your behaviour you will want to please her more than in the past and assist with the household chores particularly when you are dolled up as you put it.
    Please ensure you have all your own female wear, accessories and make up items and that you keep everything clean, neat and packed away properly your skirts, dresses, blouses, maids outfits, nighties in your side of the wardrobe.
    Al the best Darling you are going to really enjoy this and so is she xxxxx

  • Thank you again for the confidence to finally tell her!

  • Hey Buddy how are you going, I hope your wife is supportive ?

  • So far, yes. I want to slowly bring on more so I don’t scare her off and wreck my progress. I’ve worn skirts, panties and a bra with her, but my next step I want to wear makeup too.

  • Great stuff, that is fantastic just take it easy one step at a time, once you get into the makeup that will be a great step forward ensure you give her terrific sex while made and ensure she knows that is why you are so horny to give her encouragement for further progress such as a wig.
    After she is used to that I suggest you start with the heels they should easily lead into suspender belts and stockings plus pantyhose.

  • My wife does not mind me going FEMME she thinks it is cute and keeps me quiet, I have plenty of panties wear them all the time bras, nighties, suspenders, stockings, heels, blouses, skirts and dresses however I only do light makeup lipstick, mascara and rouge, I am now thinking of a nice blond wig
    My wife calls me Robin when I dress

  • There are plenty of males that love wearing lingerie and quite a lot wear panties all the time.

  • Would you tranny fucks and cucks make your own site and stop with the whole make hubby wear a wig, panties, and bras? This is supposed to be about sex, your fucked up gender shit is not sex, it’s a behavior thing. Go the fuck away.

  • This is Naughtyposts buster, your the same guy that always complains about males who love wearing lingerie and cross dressers but you keep reading all the stories I bet you have a little tug about them too EH ?

  • Lol busted

  • I really hope you love reading the posts then have a nice little tug but I can't understand why you always complain, you should make nice comments, have nothing but compliments for lingerie wearers and cross dressers almost all are straight decent men

  • It is about sex and I’m getting some great advice. Just because you’re too scared to try it doesn’t mean you should be an ass about it

  • A couple of my girlfriends three months ago were talking about how good it was to have their partners wearing female lingerie and how it had changed them in a nice way so I put it to my husband he is just too macho well I tried everything even buying pantie and bra sets that would fit him perfectly in the end I got real stroppy if he wasn't going to do it he was not going to get any sex lasted about four days but I insisted he had to wear panties at least all day before he got a shag he is starting to do what I say POWER OF THE PUSSY

  • My husband has been wearing panties exclusively for five years, about four years ago he started wearing matching bras as soon as he came in the house after six months I started making him up then another two months introduced wigs, as soon as he comes home he showers and shaves all over if necessary then puts on his panties and bra and does his own makeup and wig (he is very,very good) of an evening he wears lace nighties or teddies, he has some blouses, skirts and dresses and wears suspenders, stockings and heels.
    I think it is so very sexy a couple of my girlfriends come over and he stays dressed in his feminine gear they don't take any notice now they like him showing his feminine side, both wish their husbands would at least try it.
    Hope you do well sweetie xxx

  • That’s awesome but how would I get my wife to think like you and pursue it further with me? I don’t know how to approach it

  • Darling you have a whole heap of hints here, you have started by wearing her panties and progressed a little further she appears not to mind at all have confidence just tell her how horny you felt and would like some of your own it felt so sexy you want to try them all day, when you go lingerie shopping ensure you get pantie and bra sets at least three and try to fit in a nightie or teddie as she is with you she is at least showing support so when you wear them she certainly should not complain.
    Make sure you talk to her about it, be very attentive and don't rush things Darling I feel certain you will get there it's just the initial stages that have you worried.
    I really hope I am helping, I can feel how you really want this xxxxx

  • I really do! You talking to me seems to be giving me a bit of confidence, it’s hard cuz I don’t know where to go to read about it or have anyone to talk to about how to go about it. I think I’ll order some and surprise her wearing them. I would like to go even further (makeup etc) if she wanted it, but it’s hard to tell if women just like seeing the lingerie or if they actually want the full deal (makeup, wig, everything). Thanks again, you’ve helped me more in a week than I’ve got in 5 years

  • Darling I am so very happy I am helping you, I feel you should involve your wife in purchasing the lingerie even if just showing her the on line images you intend wearing make at least a part or agreement of the decision her's that is how your going to progress because don't forget it won't be long and you will want her to make you up and assist with shaving plus combing and adjusting your wig along with heels training.
    Take it easy Darling I am begining to really like you xxxx

  • I’m practicing on my email what I can say, this is really difficult for me cuz I don’t usually talk about feelings but I’m getting more confident I think from the advice. I like the idea of doing it together too, I really want this to happen so I need to make a plan. You’re amazing

  • I had been secretly wearing my wifes panties, until recently when after sex, i put hers on. She just smiled. I told her they hold my member nicely and feel so good. Now she has a panty drawer for her, a drawer for my underwear, and one with panties we share.

  • Darling try not to worry too much just take it easy I can see you are going to get there but be patient just one step at a time, ensure you involve your wife, if you detect rejection just hold that ground you can move forward later, I don't think you will though but don't get pushy.
    Love you Darling, I like my husband being a lingerie wearer and full cross dresser it is great xxx

  • Ditto ;)

  • Darling you both will love it first start by going lingerie shopping together and get your own sexy pantie and bra sets and some nighties, after you are used to wearing these start further with suspender belts stockings and heels they will need some work, once you are comfortable particularly in the heels have your wife start making you up then go with the wig, then you can start purchasing and wearing blouses, skirts and dresses, then go on line and order a plastic or PVC Maids outfit along with suspender panties with frills.
    Please be patient and take your time it will take some time but it certainly will be worth it.
    I went through this process with my husband we kept it to ourselves in the privacy of our own home and love it, some of our friends now know and two couples are starting on the same journey.
    All the best Darling xxxxx

  • That’s awesome ;) Thanks for the advice, I’m just worried I don’t know her limit on what she’s ok with but mines way past hers. This helps a bit ;)

  • Darling how about giving an update on your progress ?

  • I would like to just say “Mandy, I felt really horny the other night wearing your skirt” but idk what I can followup with to hint at more

  • Not much yet, I guess I’d like it if she asked me to do more and I would I just still not sure how to approach it

  • Darling don't expect Mandy to instigate everything your the one who really wants this so take ownership and start talking and acting like you really want it, be patient but slightly firm xxxx

  • Thanks Darling, just remember take it easy, be patient and talk to your wife all the time about your feelings and your next move, be very attentive and ultra sexy and do a lot more housework to help her out, make sure you at least wear a sexy nightie when making love and ensure she knows that is making you horny.
    She should quickly get used to you wearing panties, bras and nighties around the house and when you move onto suspenders, stockings and heels start shaving all over she can certainly help, ensure she helps you with advise and watches you to give encouragement.
    The rest should just progress naturally but again Darling don't push things too far at any given time you can always pause hold that ground and progress further again later.
    Wishing you both the very best Darling xxxx
    You may get some negative comments on this site just take no notice, at our favourite lingerie store the assistants tell us all the time more and more males are buying their own lingerie and asking advise.

  • Ask her. Or wait for Halloween.

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