Crossdressing & Much More

I have been crossdressing since as far back as I can remember. I think it started when I was playing on the floor as a child and looking up at my aunties sheer seamed black stockings and black court high heels. God I loved those stockings. I then started to borrow my mothers nylon panties and sheer full slips to wear when she was out. I remember getting caught a few times too. When I stayed over at my grandmothers I would borrow a full length black nylon lacy petticoat and sleep all night wearing it before returning it in the morning. Eventually I started buying my own female underwear and still love going into department stores to purchase items especially fitting into the conversation somehow that they are for me. I regularly wear sheer nylon bra & panties under my male clothes.

As I said I have crossdressed for years and have grown to love other things too like TV domination (Love being dominated), bondage and spanking (I have a leather crop and a leather multi tail tawse), experimenting with getting wet in the rain or in streams (Nylon clings amazingly when wet) and humiliation is a lot of fun too. I regularly worked late and would change into my favourite bra and panties with suspenders and seamed stockings and lovely nylon full slip then walk to the car in the dark and drive around for hours. Very humiliating driving through towns with street lights or stopping at traffic lights with cars alongside who maybe looking at you and you can't do anything until the lights change.

I love a frilly maids outfit with black sheer panties & bra with lacy suspenders & seamed black stockings the best as I like the thought of servitude and being tied up and spanked. I love dressing in this naughty way but then I have to be punished with a good spanking for it. Pleasure & pain I suppose.

Basically I am willing to give anything a go for the experience and things I have thought of include nettles in my panties or playing with hot candle wax etc etc.

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  • Mmmmmm You sound like my twin I’m in California leave email if anyone in Long Beach area and love a silky crossdresser!

  • Darling, I completely understand how you feel when you put the silky lingerie on, it's wonderful, so sensual so erotic.
    I have been feminising since I was in my early teens, but I had admired girls and ladies underwear long before that. When I reached puberty I crossdressed at first with any knickers or slips I could get hold of when visiting friends houses or from washing hanging out to dry. I would get a raging erection whenever I spotted a lacy nylon slip or frilly panties wafting in the sunshine.
    I was able during the "Beatles era" to grow my hair long, shave my body hair and generally cultivate my feminine appearance.
    My parents accepted that I was gay but no-one commented on it, I got a job in the fashion business where a lot of men were gay or bisexual and I became more and more feminine, wearing silky ladies slacks blouses and eventually a bra when my breasts developed. I am now a mature she-male, fit attractive and with regular boyfriends who love holding my erection as they fuck me.

    I have always been highly sexual and I adore making love with an older man as they are so appreciative, having a chat in my apartment and coffee then undressing themselves, taking my dress or skirt and blouse off while they stand naked in front of me, then taking me in their arms and caressing me in my lingerie, feeling my breasts, lifting my silky slip and stroking my erection trapped in my silky knickers, then I kneel down kissing their aroused penis until its fully erect, then lead them to my bedroom where we lay on the bed smothering each other with kisses, caresses and then they take my knickers off, lift my stockinged legs over their shoulders and I watch as their erections thrust into my anus and we make wonderful love with me pretending I am a wife.

  • I'm 61 and in good shape. I would love to be with a crossdresser. I love the way you dress with black thigh highs or garters. Love stilettos. Love to take u out for dinner dressed up like that with a black short tight skirt. Then I'll take u back home and take your dress off and just adore u walking around the house like that. That would turn me on.

  • Darling, you are the right age for me and I believe you would adore the way I look. A feminine body with a decent penis, the very best combination, I know what men like.
    I would greet you at the door of my apartment fully dressed En-femme, with my High heeled white stiletto's and my flouncy, flirty silk dress all pink and femme, with a slightly "see-through" top that shows off my pink lacy lingerie underneath. We would hug each other and your hands would wander down my silky dress to fondle my bottom, feeling my silky undies and suspenders.

    We would then go into my lounge and I would go to make a coffee for us and you would follow me into the kitchen and come up behind me pushing yourself into me with kisses to my neck and I would feel your hardness trapped in your trousers pushing against my bottom. Oh! I would let out a little moan and you would turn me around pulling me close feeling my erection held within my silky knickers and kiss me passionately.

    You would unzip my dress letting it fall to the floor as you ripped your clothes off until naked and with me standing there in my silky lingerie watching, I would marvel at your erect manhood throbbing with desire. You would lift the hem of my lacy silky slip revealing my stockinged legs and silky knickers also bulging with my erection, we would cuddle close feeling each other, kissing, thrusting with our excitement, then not waiting for coffee, off to the bedroom my darling, with you watching my cheeky bottom wiggling in my lingerie as I mince across the lounge.

  • I would love that

  • I want my email I like your style. Want to hear more. Your so sexy.

  • Darling, thank you for your words of appreciation, would you like to know about a recent sexy encounter I had with my male neighbour who is in his late sixties and very horny?

  • Yes, I would love to hear about that. You are so sexy from the way you dress to the way you talk

  • Thank you darling. Well I was going to tell you about my elderly neighbour Jack, he's in his late sixties, married and horny. He stopped me in the street some time ago and I was dressed En-femme and asked me if I was she-male and I nervously answered "yes". He told me I looked great and did I fancy having him at my place for some fun. I knew full well what he meant and I agreed. Well, it was 9.30am the following day and I was still in my floaty vintage negligee and silk knickers, I looked out of the front window and saw Jack standing there, with a bunch of flowers. I opened the door and let him in, shut the door and turned around, he had dropped the flowers onto the hall table and he took me in his arms and kissed me passionately. I could feel one hand caressing my body through my negligee, my penis became instantly erect with his touch, his hand went round to my belly and wandered onto my erection, "oh! you are a lovely girl aren't you, so sexy", he lifted my negligee and his hand went inside my silky French knickers, he was so gentle, still caressing my penis and with his other arm around me pulled me really close. I could feel the bulge in his trousers as he whispered "I want to fuck you are you ok with that", I kissed him, he smelt so good, I loved his after-shave fragrance and said "yes please but be gentle" and I led him into my bedroom.

  • Part 2:
    I watched as Jack took his clothes off, admiring the was he folded them neatly on a chair and then he stood there in his boxers and wow! was he aroused. I gawped at the huge bulge with the end of his penis almost out of the elastic at the top, I went over to him, kissed him and then went down onto my knees slowly pulling the elastic top away from his waist. This magnificent throbbing erection appeared, it had a slightly upward tilt and was alive as I leaned towards it and licked its head flicking my tongue over it. I tried to get it into my mouth but couldn't so I flicked my tongue up and down the shaft as I took his boxers off, he opened his legs and offered his testicles and I licked them too, then he lifted me up and kissed me and whispered "lets go to bed".

    My bed was unmade and I watched as he lifted the duvet and asked me to get in and with a gentle smack to my bottom he got in next to me. Oh!!! my goodness it felt so sensual as he pulled me close under the privacy of the duvet, I felt like a little girl in her silkies, I was completely helpless as he spread my legs and got on top of me. I felt him lift my negligee and kissing me he whispered "lift your legs and wrap them around me darling", I could feel his erection under my bottom, he was pulling the crutch of my knickers away from my anus and I felt his finger enter it, then two fingers then three, I wanted him, I knew he wanted me, I spontaneously lifted my hips and then the shock of that monster thrusting inside me, I squealed and squealed, I couldn't help it, Jack didn't stop, instead he kept kissing me and saying "it'll be alright, it'll be all right, I love you". I tried to tighten my legs around him, I felt my penis rubbing on his hairy belly, then I felt him cum, oh! my goodness he could really spunk as I felt the first two spurts and then with some final exhausted thrusts it started pumping out of my anus.

  • Part 3:
    We have become lovers and Jack likes to make love to me when I dress in stockings, full waist suspenders and silky lingerie. He is such a naughty man and I love it when we go to bed together. XX

  • Jack has been my lover for 6 weeks now and we meet at least twice a week but it has been three times when he has been feeling randy!! He has become much more at ease and also more adventurous. He still brings me flowers but has also bought me lingerie that he prefers, like satin frilly sissy knickers with a fashion crutch less front and back. Jack says he loves it because he can leave my knickers in place and penetrate my anus through the lacy space. In return I bought Jack a silk robe to wear when he takes his clothes off as we relax now before going to bed. I just love laying on the settee with my head in Jack's lap and feeling his magnificent penis throbbing and twitching beneath my head. One day he was really naughty and he pulled his penis out from under his robe and I was loving and licking his penis head when he ejaculated, I just couldn't resist slurping his semen up!!!!
    He loves me to be fully dressed when he visits, he says he loves the surprise when he takes my dress off in the bedroom and sees the type of lingerie I've chosen for him. He is so gentle and loving when he removes my dress, hanging it carefully on it's hanger and I'm standing there in my undies. Jack holds me and I undo his robe, I pull his naked body back against me, Oh! he is such a man!! He kneels down and removes my heels, my penis is erect and protruding from my knickers, Jack mutters "lovely" and places my penis in his mouth,"Oh! Jack, oh! Jack" I moan, "don't make me cum to soon not before you fuck me"
    Jack leads me to my bed, pulls the duvet off and lays me down. He stands by the bed, his big member is throbbing, I can see it "oh! take me darling I plead" and then I watch as he lifts my legs, gets between them and pulls my bottom towards him.

  • Part 2:
    He fingers my anus brilliantly, I'm writhing as they penetrate me and with his other hand he is caressing me, my breasts, my suspender covered belly, my stockinged legs as I prepare for the shock of his entry. Then it happens, OMG! he's big, I can't help screaming, I do it each time as however much lube I apply, its the sheer size of his penis. The initial discomfort fades and then he's so forceful, my man, I pull my breasts from my bra, "kiss them, kiss them" I plead and Jack leans forward over me and gently nibbles my nipples, I'm in bliss!!!!
    He takes much more time and care now before he ejaculates and always tells me when he is about to cum, I clench my buttocks tighter, hold my legs tighter and thrust myself upwards to his rhythm. "My baby girl" he moans as he pumps his love juice inside me, Jack now always lets his penis stay in me while he masturbates me to ejaculation and sometimes when he is doing this his penis hardens and he fucks me again! I truly love that it demonstrates true love and desire!!!!

  • Your really having a lot of fun aren't you ?

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