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Crossdressing
And wearing women's panties in general
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Updated 1/05 [M] I was very interested in the many letters sent in from men and their wives about cross dressing and the pleasure they derive from it. My only instance of real cross dressing came about as a Halloween costume my wife put together for me one year, I dressed as a hooker. She actually went out and bought me thigh high nylons, panties and a bra all to size along with a skirt, blouse and high heeled shoes. We borrowed a neighbors wig and my wife put make up on my face. I was a real hit at the Halloween party we attended and received best costume. Later in the evening, after many drinks, I admitted to my wife how turned on I was by wearing women's clothes and that the panties rubbing against my cock were giving me a perpetual hard-on. She playfully grabbed at my cock and told me we would have to take care of "him' when we got home. She was good to her word as the minute we arrived home after the party she initiated sex. I fucked her still dressed in my thigh high nylons and panties (pulled to the side). It was incredible sex and my orgasm was unbelievable. I had not cum that hard or that much in months. I fell asleep that night still wearing my thigh highs and panties. When I woke in the morning to our chagrin, my cock was as hard as ever and we once again had sex. My wife joked with me all the next week about how excited I had gotten dressing up as a woman and how hard my cock had gotten from wearing panties. She went so far as asking me if I would like her to pick up a few pair of panties for me the next time she went to the mall. Of course, kidding, maybe more serious than I would admit to, I told her "of course". Well, she did and I got some and I wore them from time to time. On occasion I would wear a pair of panties to work in the morning and come home for a preplanned "nooner". Wearing them never failed to get me hard. In fact even during our fucking I would leave them on and just pull them aside, my cock standing hard, waiting in anticipation of what was to cum. To this day, the minute I pull on a pair of panties my cock gets hard immediately and to this day my wife still enjoys me wearing them, knowing I'll be extra turned on during sex.
[M] I began playing dressups w/ a rather young and pretty aunt - she would dress me up in her lingerie, clothes and makeup - it was fun and I loved it - I was probably somewhere between 4 & 7. Over the years I continued on my own - secretly dressing in my mother's clothes and makeup when I was alone.
It was always relaxing and exciting at the same time - I never wanted to become a girl - but I sure did dressing up like one. In my teen years I started becoming sexually aroused when playing dressups - not sure what to do about it I did fantasize about being w/ other men - after all I was dressed as a woman - loved to dress as slutty as possible - stockings and heels became a must w/ any outfit -
I was not a "sissy" - anything but - I was a jock in high school - very popular w/ girls - dated a lot but still loved my time playing dressups and fantasizing
Like most young boys I did experiment w/ a few guys - the usual jerking off - but one friend, Warren, was different. He gave me my first bj one day in the woods after loosing a contest - while he sucked my cock he swung his legs over my head with his cock inches from my lips - after a few moments of thought I took him in my mouth and sucked him as he did me...
A few weeks later, w/ no one home, I invited Warren over. When he came over I met him wearing a sexy sheer gown, stockings w/ garters holding them up - makeup and a wig of my mothers - at first he nervously laughed but I told him this would be a lot of fun - soon we were in my bed - I was sucking his cock and pinching his nipples - before the afternoon was over he was calling my his girlfriend -
Over the next several years we played quite often - Warren never dated in High School - I was always going out w/ girls but on days when I had off from practice we would meet at one of our houses -
Our hottest time was when I was being initiated in the letterman's club. The last day of "hell week" we had to go to school dressed as girls - gee what a burden! Anyway his mother heard me telling him about it and volunteered to help me dressup - so that morning before school she laid out a dress, lingerie, stockings and heels and did my makeup - that had me so hot and horny all day - what she never knew was that afternoon while still wearing her clothes I screwed her son in her bed!
Updated 10/04 [M 48] My wife and I have been enjoying this special turn-on for about 3 years now. After I confided in her that this was a secret fantasy I had, she bought me a gift of thigh-high satiny black stockings and black high heels. Since she had a dominant side, she insisted that I put them on and parade around in front of her, naked except for these two items. After some initial shyness, I realized that I had exhibitionist tendencies and totally gave into them. What a turn-on! She loves to take charge and I love to exhibit. It didn't take long for me to become comfortable in the high heels and I loved the new sensations and the special "strutting" posture they gave me. Well before long, she began buying other sexy items for both of us - colored stockings & panties, wigs, and even corset's - not to mention some sexy miniskirts and tops. Now we go shopping together and I've even become bold enough to go into the fitting rooms to try things on. Since we are both quite slim, we can often wear the same items. Also, as an added turn-on, I now keep myself totally shaved from the waist down and love the sensation of these wonderful feminine garments against my smooth, bare skin. On extra-special dress-up nights, I will also do lipstick, rouge and eye shadow. You can't believe how this whole adventure has enhanced our sex life. More men should explore their feminine side and try this! We've lately had the fantasy of meeting another couple with the same fetish for sexy dressing. We'd love to hear if others have this very special interest and what they do with it.
Updated 1/04 [M] Not all people can express themselves with a paintbrush, camera or pen but
everyone needs some sort of a "this is who I am" statement with their
persona. I see fashion as the great equalizer between very creative people
and the not so thinking out of the box personalities. In other words, some
people are a pair of silver sparkely butterfly applique open toed ankle
strapped 5 inch stilletto heeled sandals and some people are a pair of brown
flats. Our clothes tend to define who we are or at the very least, who we
would like to be. Unfortunately this seems to be true predominately for
women. I say unfortunately because I am of the fashion challenged sex more
commonly known as male. I could have also named this essay My Life in Brown
Shoes.
To be and feel classy a girl may don her little black dress, pearl earrings,
and a pair of satin sling back heels. For comfort she may wear some
low rise jeans or sweats or her significant other's big shirt with a pair of
tights. Wearing an "up to there" mini- skirt, painted toe nails, and
nosebleed height open toed mules would definitely put a chick way up on the
"sex-o-meter".
But what's out there for the guys. Guys have different moods too but if you
want to spell it out in wearing apparal it would be something like jeans,
tee shirts, and sneakers. Oh yeah, and maybe a pair of brown shoes. One
other thing. We do have suits. They haven't changed much in the last 150
years but it is another option. To add some personal style more creative
guys mix and match their suits with a pair of Nikes. Eeech. Bring on the
brown shoes.
If all these fashion choices for women isn't enough, women can wear guys
clothes and look really cool. What chick doesn't look sexy wearing a man's
over sized white shirt or a plaid flannel shirt with work boots. Men's styles
have also crossed the line into women's fashion such as oxford shoes,
mountain and hiking boots, tuxedo pants, trouser socks, boy-leg bikinis and
boxer shorts.
The male population have just begin to cross the line of fashion. Some men
sport earrings on both ears. A few can be seen wearing ankle bracelets.
Male celebrities have been photographed for national magazines wearing such
feminine adornments as bright red toe nails but looks like that makes news.
A woman wearing a man's suit and necktie may be photographed for a national
magazine but not for that reason.
It's time to change this double standard and be free and without ridicule to
wear what we want and not wear what we don't want and if we don't want to
wear anything at all that would be a choice too which brings me to my next
point. Women also have fun with what they don't wear. Examples are belly
and butt baring ultra low-rise jeans. Thong bikinis. I have actually seen
thong bathing suits for sale that was thonged both back and front. Where do
you go from there. Don't forget up-to-there skirts and down-to-there tops.
Or how about those cute little baby tees with the cleavage nestled so
snuggly in an appropriately placed little v-cut. A guy exposing half as
much skin would be arrested. Actually some guys probably should be.
Nakedness should be practiced with discretion. But if you're a pretty
naked person I'd say go for it. Remember, if fashion is art then a naked
body is like a canvas without paint. That doesn't sound very obscene to me.
Art knows no bounds so neither should fashion. Women know that already so
it's about time for the guys to get out of the garage, clean the grease from
under the finger nails and head for the local pampering spa for a manicure,
pedicure, and make over. I think conversation could change from "I need a
beer or what the fuck. Some fucking fuck is fucking parked in my fucking
drivefuckingway" to "what do you think dear, does this pleated skirt work
with my new peep-toe pumps and should I wear my sheer or opaque stockings".
If nothing else, the fashion choices would consume all the guys free time.
Short skirt, long skirt, skirt to the knees, trouser socks, control top
panty hose, sheer to the waist panty hose, reinforced toe, sandal foot, thigh
high hose, gartered hose, no hose at all, bikini panties, thongs, high rise,
low rise, , sheer bras, satin bras, lacy bras, full cup bra, demi-cup,
push-up, padded? And what about the shoes? Flats, mules, stiletto pumps,
high heeled sandals, peep-toe, espadrilles, sling backs? Pheew!! This would
keep a guy so occupied I think that we would all get along so much better
and there would be no more wars. That's just my theory.
In summary, I would just like to say that a man walking down the street
wearing stockings and high heels is not necessarily a homosexual. A man
walking down the street wearing stockings and high heels is not necessarily a
cross dresser. A man walking down the street wearing stockings and high heels
is not necessarily effeminate. But if you see a man walking down the
street wearing a pair of 4" stilletto heeled pumps you can surmise that there
are two things you can be sure of. He's wearing high heels and his feet
probably hurt.
[M] I've liked the idea of cross dressing, but have mostly been unsatisfied by the actuality. I've tried on my wife's panties several times, sometimes at her suggestion. (We are about the same size in the hips) When we married, I started buying her cute panties, and she knows I like seeing her in them (and getting her out of them.) Anyway, I found they didn't hold my 'package' very satisfactorily at all (either my dick or my balls spill out the side). The best of her undies that I've tried are her 'boy cut' panties, which are a lot like the boxers I usually wear. (Tighter in the legs) I liked the nylon feel, and she has subsequently bought me some nylon mini boxers that ride down on my hips and just barely cover my package. I like the nylon feel. Her boy cut pants have a good feel, but they are difficult to have on and pee. I like the way they grip my legs and groin.
One of her things I like to wear sometimes is her tube tops. I've written you before that I am a breast sensualist, and love to have my nips played with. This is the quickest and surest way for me to get an erection. Sometimes she will tweak my nips just because she likes the reaction, when we know we can't do anything (don't have time) with my resultant erection. Anyway, I like the feel of her tube top gripping around my upper chest, the feeling is sexy. I don't wear one very often, but sometimes she or I will put one on me just for the feeling. She and I both routinely initiate something akin to foreplay when we don't intend to have sex, it's just part of the way we play. My nips show thru the tube top, just like hers do and it's fun to have one on and have her play with my nips that way. Quite routinely when we are sitting together on the couch watching tv, she or I will tweak the other's nips just for the reaction when we have no intention of having sex right then.
[M 46]It's very strange. Some years ago, I found a number of websites of cross dressers, and found them highly arousing. I even found one in the Philly area and considered meeting her just to go shopping in a mall. I wasn't looking to "hook up," but somehow found the whole idea appealing. At the same time, I wondered if I had any cross dressing fantasies. Well, some months later, I was staying with a friend in DC to save money for a conference and stayed in the bedroom of her housemate. That night, I decided to try on the housemate's clothing to see how it felt, and was somewhat surprised to have absolutely no reaction at all. I guess its one thing to see someone else look really good in women's clothing, yet I guess having myself in them doesn't do anything for me at all.
Updated 11/03 [M] Joan I don't really enjoy crossdressing, that much, but the letter that starts off; "My husband is a dedicated BI crossdresser and I am BI also. " is just an incredible turn-on. It really makes me want to try some of the things they (She) talks about. Before I married, a girlfriend who I was pretty serious with, used to tease me about wearing her things, which I usually didn't care for, but one time after sex, she talked me into putting on her 'flutter' panties. To my surprise, I got an immediate erection, which she said meant that I really wanted to dress in women's clothes. Once I wore a pair of her flutter panties when we went out, and kind of liked the feel of them, but they were like not wearing anything. A few times after that she talked me into putting on her things, she even bought me panty hose, but after the initial surge, they didn't really do that much for me. At any rate, I don't think I am a natural crossdresser, but this story really triggers something. I hope this writer writes more and amplifies her story.
Updated 9/03 [M] i see that you have some writings on crossdressing. whereas i prefer to name my particular fashion persuasion as "fashion freedom" I also enjoy wearing certain clothing, hosiery, and shoes that are for some unobtainable reason always found in stores categorized as WOMENS. i enjoy writing mostly about personal experiences and my perception of these experiences. i find a lot of humor in life and as a perceiver and perseverer of truth i find a lot of humor is society's contradictions. i once went into a shoe store to buy a pair of shoes that were located in what they have labeled "Women's shoes". i went in wearing a pair of white high heeled dress sandals with nude stockings. the women working there were so upset they called the police and the police came and talked with me and said that the women were upset and that they didn't want me going into their store again. just for wearing womens shoes. i could understand it if i was wearing white past labor day. i should be arrested for that but this was in the middle of the summer. oh well. i'll save it for another writing.
[M 50] I've been wearing "ladies" panties forever it seems. As a child I would often try on my mom's panties, stockings, girdles, slips and bras when she was at work. I loved the feelings that I got when wore these items. I used to wonder why it was only females that were allowed the pleasure of wearing these sensuous clothes. Although this stayed with me over the years, there were large periods of dormancy. But within the last years these feelings have again come alive. I have been married for nearly twenty years. I thought that I could tell my wife about this but the results were disastrous. In fact she bought me two pairs of panties in my own size, but later decided that men who enjoyed these activities were really sick and she wanted no part of it, She said that she thought I was joking and she did it for fun. She never in her wildest dreams considered that I would enjoy wearing them. After this announcement almost cost me my marriage, I've returned to the closet. I now am able to communicate and learn from others about their experiences with crossdressing, some say they will never tell. Maybe I am sick, but I often find myself wondering why some women think that they should be the only ones allowed the privilege of wearing clothes that feel so good.
Updated 9/01 [M 50] My name is Mike I got into wearing nylon at a young age 15-16 and it has
become a pleasure which I still enjoy today at 50- sooo- silky
Updated 6/01 [M 34] I'm 34, married and I love to dress. My wife got me started dressing. The
most exciting time is when she takes me shopping for clothes. The feeling of
slipping a pair of silk panties and a skirt on and a pair of heels is
erotic. The feeling of wearing a pair of woman's dress pants and blouse with a
pair of heels is a great feeling.
Updated 3/01 [F] My husband and I have been following your column for quite a while and
we have gotten some good ideas from your readers who write in. I would
like to tell you about our experience which happened partly as a result
of an article we read.
Updated 10/3/00 [M] I read your articles but have never posted before. I am a crossdresser
who has rhe help and approval of spouse.
[M - now becoming F] Just another chapter in our ever expanding sex life and we have been
really having fun. As you know I am now a full fledged crosdresser with
a wardrobe that most real women would envy and I am enjoying the feel of
pretty silky panties and other underthings. I have put most of my male
things away and wear only female lingerie now .I have really become
good at my female mannerisms too. We ordered a tape from a TV site on
the web which tells how to train your voice and it is really working now
that I have finally learned how to use it. My voice is really sounding
fem now and I fooled a woman on the phone the other day and she thought
I was a female. I call different places and so far all of them think I
am a woman. I am feeling a lot more confident now that my voice is
better.
Updated 9/4/00 [M] This is an update on my last post from 8/1/00. As you may have read,
my wife and I have just started to swap with other couples and I have
now become a dedicated crossdresser and I am now BI as well as my wife.
These things have all taken place in a few short weeks and we have
really been active
sexually.
In our last post I told you about our meeting with our first BI couple and
how we both experienced our first BI sex. My wife tried double
penetration for the first time and wanted to try triple penetration.
Well, we have since expanded our horizons a little more and here is a
account of some of our
activities.
And a follow up from the same person I have written you several times and you have been nice enough to post
my letters so here is the latest in my progression from ordinary male to
a BI Sexual crossdresser. After thoroughly breaking me in with a dildo
as you know we had our first swap where we both experienced the joys of
BI sex. We have both been very active since and I am now pretty much of
a slut as I can't seem to get enough male attention. I lay there as I am
fucked by another man and just hate to see it end as I enjoy the
penetration so much. My greatest thrill is when I am penetrated at both
ends and I can enjoy the thrill of sucking as well as being fucked. My
wife has become a devotee of BI sex and is really enjoying every minute
of it. She is also enjoying the many men that are available now that we
are swingers. She had her first triple penetration recently and that
was a fantasy she had for a long time. I find that I love to watch as
she has sex with all those guys.
Updated 8/1/00 [M] You may remember that we were into dildos and I was starting to
cross-dress more and more as our sex life opened up to new things.
[F] I have been reading stuff on your site, and I am
greatly intrigued my seeing all of your letters. I am
writing about my boyfriend. It may seem weird, but he
likes wearing my underwear, especially the satin ones
that feel smooth on your body. He told me that he
likes wearing my dresses when I am not home. His
favorites are the ones made of either satin or rayon.
He like the way the feel on his body. He has also told
me that he fantasizes about being tied up and
blindfolded while wearing my dresses and skirts. So,
one day I tried it on him. The fact that he seems to
want to pretend to be a woman, and also knowing that
he cannot see what happens to him when I touch him, it
is a great turn on for me and him. He really likes it
when I strap my dildo on and have anal sex with him.
You can add this to your website, because it might
shed some light on what other guys think of doing or
have done even though they have never read anywhere
else about it.
Updated 7/1/00 [M] I have an article that you have already posted telling about my wife
taking me with a large dildo(Posted in June) . I mentioned that she had
bought me a pair of panties and a sexy baby-doll to wear when she 'raped'
me. This letter is just to update you on our progress.
Updated 5/30/00 [M] I have written you a couple of times before but I must tell you about
our most recent discovery. Since we have been reading stories on your
site as well as other sites my wife and I have really been widening our
sexual activities. I had always assumed my wife was limited in her ideas
about sex and that I was the one who had all the fantacies. Was I ever
wrong!! She hs come on like gang-busters and is game for just about
anything now.
Updated 1/1/00 [M 17] I am a 17 year old male that has been into privately
cross dressing. When I was young, I used to go to my
sister's room and take her bathing suit out of her
drawer and go back to my room and put it on. It felt
really good, because it was a tight one piece suit,
and it hugged my body and privates. Then I would
usually masturbate by sticking my left hand into the
side and jerk off. It felt good when the cum would be
all over the inside of the swimming suit and it would
be warm against my body.
Updated 8/7/99 [M] Hi- In response to cross dressing. I'm hetro and living with
my lover. I am slender and fit, my lover has gotten me a couple of pairs of
men's thongs, which I have worn and like. They hold my package tightly and
feel sexy. My lover can't keep her hands off of me when she knows I'm wearing
them. One day I was folding some laundry she had left in the dryer, including
some of her panties. I couldn't help but to notice their similarity to the
thongs offered to men. This curiosity led me to try on a pair of her silk
underpants to see the difference. I must say, they felt so much nicer than
briefs that I wear. They fit tight and smooth, very much like my thong with
the exception of less "pouch" which made the feeling even tighter. I do not
find any interest in any other articles of her clothing, but the feeling of
those panties was great. I have never let her know about this in fears of her
reaction, however, I have taken to wearing my thongs more often and am always
looking for men's underwear that could give me the same feel.I wish makers of
men's undergarments would include sexier cuts with smoother material like that.
[M] About men crossdressing: as a teen I stayed w/a friend overnight to
awaken at 6 am tied up and striped...he shaved me neck down and put his
mpms lingierie on me...then after pictures he took of me I had to do
whatever I was told or the pics would be shown! He padlocked high heels
on me , and walked me to the neighbor lady (73) where he forced me to
jack off for her and when she realized I had to do as told she wanted to
see him fuck me! Just the beginning.....
My husband had a very responsible position in a local business and and
we are 43 and 40 years old, me being 43. We both were pretty active
sexually before we met and I had experienced the pleasures of anal and
oral as well as BI sex . I went down on my first penis while still in HS
and enjoyed my first BI experence in college. I worked for a boss after
college who opened me up to anal sex.
I am a well built but larger than average woman and when I met my
husband I never dreamed I would marry him. He is only 5'7" tall and
almost petite but he has a penis that most men would die for and he has
unbelievable staying power, something that I had come to enjoy in a
previous relatioship.
I am a woman who prefers well endowed men and for me a larger than
average penis is a must. On our first date I could not believe it when
my husband dropped his shorts and showed me an almost ten inch penis
that was so thick I could hardly get it between my lips. My jaws
actually ached from sucking him to a climax and when he went into my
vagina I never felt so fullfilled. I just couldn't get enough of him and
we had sex so many times the first week I was actually swollen and sore.
Needless to say I married him and even though I stood two inches taller
he didn't seem to object when I wore high heels .That was before he
confessed to being a long-time crossdresser. To tell you te truth I was
not supprised when I found out as I had seen feminine traits in him
before. He shaved his body hair long before we met and I liked the
smooth feel of his body. He wore his hair long and usually in a pigtail
at work.
We talked and I agreed to at least trying to go along with it to give
him a chance. The first time I saw him fully dressed in lingerie I could
not believe my eyes ! He looked just like a female and the high heels
made me realize that he had better legs than I do. I don't know i it was
the fact that I am BI or what but it turned me on like never before and
a few minutes later I was down between his stocking-clad legs sucking
for all I was worth. Later as I lay on my back with my arms around his
bra covered chest I felt hi silky stockings rub me as he sank his
beautiful organ into me over and over for nearly twenty minutes.
After that he wanted me to become more dominant and soon I was using a
small dildo and I would penetrate him just about everytime we had sex.
Finally one night we ordered a very large dildo and a strapon harness
from the Net. Six weeks later I took him like a woman and as I sank the
ten inch dildo into him as far as I could I felt a power that stayed
with me log after I pulled out of his distended ass. He was by then
wearing panties all the time and bras as well, even to work. I kept a
few pieces of male underwear for emerginces but when home he started to
wear dresses and women's attire almost completely. We went out and
bought him nighties and frilly things to sleep in. I had worked part
time in college for a cosmetic company so I soon had him doing his own
make-up and he was very good at it.
I loved our situation as I was in complete control of everything. After
bossing all the people at work all day he was more than happy to have me
take over when he got home. It became a challenge just to see how fem I
could make him without our friends finding out. I plucked his eyebrows
and sent him in with very light make-up several times but no comments
came his way.
One night we were watching a XXX movie we had rented and it was about BI
crossdressers and several scenes showed TVs being penetrated like women
. He asked if I would ever consider letting him be with a man amd at
first I said "No" but as I thought later I agreed to go along if I could
dominate the other guy too.
That was the beginning of a new life for us as after finding an
abundance of men who wanted to be fiminized by a dominant woman we
started to check out and often meet men in my husband's situation. Most
had wives or gitlfriends that did not approve and we were kept busy with
replies to our emails. I will never forget the first time I saw a
lingerie clad man slip his large penis into my little girlie husband and
make a slut out of him. He almost went crazy as he pushed back against
the guy trying to get more of him inside. I have also had several
opportunities to indulge myself with my Bi desires with some of the
wives who came along with their sissies. My husband is really fem now
and we go out together and so far no-one is the wiser. We sold our part
of the business and as a result of good investing no longer need to
work.
I have become nearly a full-time DOM now and have regular customers who
visit me. We have built up a stable of safe, clean men who we work with
as well as several SOs. My husband loves it as he is used often as a
female and gets to perform oral and anal almost as often as he wants.
We have stopped advertising on the net as we have a full schedule.
I know this is a long letter and some may doubt my sincerity but believe
me it's all true and there are a lot of parts I have deleted just to
shorten it......I realize our situation may be unique but I would love
to read others comments about our lifestyle.
When I married my husband I was a very
inexperienced almost nieve woman. I had only had sex with one other man
a few times and it was straight, fundemental sex with no frills or
foreplay to speak of. When I first met my husband I was a little
hesitant to date him as he is only 5'6" tall and when I get into heels
I am actually taller than he is. After much persuasion I finally
consented to date him.
What followed was some of the best sex you could
imagine! Over a period of several weeks he taught me to love oral sex,
something I had never considered before. And after careful
preparation I allowed him to take me annaly. You have no idea how out of
character that was for this little nieve country girl who was raised in
a very religous household.
So you see I have come a long way. But the main reason I am writing is to tell you what has happened in the
last few months. It all started when we rented some XXX movies. I had
never seen one and I was anxious to see if all I had heard was true. One
movie showed a woman with a strap-on dildo giving a man anal sex. My
husband kept re-winding and viewing that scene over and over again. I
enjoyed the flicks and they made me very horny so after a serious
session of first oral and then anal sex we lay talking in the bed. My
husband asked me how I felt about the woman penetrating the man with the
dildo. I must admit it did excite me a little as most of the movie did.
After a while my husband admitted to me he had always had a desire to be
penetrated back there and a I agreed to try it. We sent for a large
dildo from one of the web sites which sell them.
Two weeks later it
arrived and we prepared for his "deflowering" as he called it. We
learned from reading your column about taking an enema before anal and
so I helped clean him up good. We used the same lube we used when he
took me for the first time and I mounted him. The dildo was large but he
wanted a big one so I took my time as he was very small back there. As
I penetrated him the first time a strange thing happened! I felt power
I had never felt before in my quiet conservative life. I could see us in
the mirror beside the bed and I really got into the action. The pressure
from the dildo against my vagina was wonderful and I got more and more
agressive as I penetrated him time and time again. He was moaning and
whinning like a young girl and asking for more and after several minutes
I climaxed like I have never done before. My legs grew shaky and weak
and I had to sit down on the side of the bed after pulling out of his
posterior.
Needless to say we started to indulge frequently and eachtime I had a shattering climax. I would then perform oral sex on him to
enable him to get his release too.
The next step of our progression came one night after he had rented
three new XXX movies and we had retired to the bedroom to watch. One of
the movies was a transgendered movie showing a man very convincingly
attired as a woman. I could not believe he was a man until I saw his
penis! To make a long story short a week later I agreed to let my
husband dress female while I used the strap-on toy. He told me to go
into the bedroom and wait for him. I heard him moving around in the
spare bedroom and when he finally came through the door I couldn't
believe what I saw! He was dressed in panties. garter belt, bra, and
high heel shoes! He had his own wig and had done a great job on his
make-up. Even as nieve as I was I knew he didn't just happen to have
all these female clothes on hand and after several minutes of
conversation he admitted to me that he had been dressing this way for
over a year while he was home alone.
I was a little hurt a first that
he had not told me sooner but actually he looked so cute as a girl I
just couldn't stay mad at him. He looked so vulnerable sitting there on
the bed. Before I knew it I was cuddling him like a daughter more than a
husband and a few minutes later I was taking him or "her" with my dildo.
I don't know if I have BI tendences or not but I really enjoyed having
this little girl-like figure under my control and I climaxed that night
like never before and a few days later he dressed completely as a woman
and when I came home from work he was waiting for me. I was supprised to
say the least and mostly because he is so convincing as a woman. He even
practiced his voice and he sounds much like a female. His small framereally lends to the image too.
We still have great man to woman sex but now he wears female clothes at
home most of the time now and he insists on doing most of the female
things in the house that I normally did. He wears his panties and
stockings to work under his male clothes and changes as soon as he gets
home.(to female clothes) He is an insurance agent so he has his own
office and can get away with it. I don't know if what we are doing is
considered perverted but I know we are both enjoying it and I do a lot
less housework now. We are considering going out with him dressed
female soon and I am very convinced no one will catch on.
Several years ago we were invitied to attend a masquerade party given by
the lodge that we attend. It was for a charitable purpose at Xmas and
my wife suggested I go in drag and I agreed. Let me say this : I had
never crossdressed or even thought about it and was a little reluctant
when she brought the new pink panties and other lingerie home from J.
C. Penny stores. She insisted on being realistic as they were giving a
nice door prize for the best and most convincing costume. I hesitated a
little when she wanted to shave my legs but in her usuall way she
convinced me and rewarded me later that night with great oral sex. She
knows the way to my heart.
As I stood in the shower she proceeded to shave me and ended up shaving
me all over "To make it look right" I stepped out of the shower and
dried off and I really liked the feel of being shaved. Next she had me
put on the silky pink panties and when they slid up my legs and I felt
them around my hips I got an instant erection!! I could not believe how
sexy I felt. My wife was really enjoying the fact that I was
co-operating so willingly and she was smiling from ear to ear. I think
I was really hooked that night and didn't realize it.
It took awhile as my wife is a perfectionist but when she finished by
adding make-up and wig I was amazed at the young woman who was looking
back at me from the mirror. I am a very small statued man and my small
feet and hands really looked fem. She had purchased a pair of shoes from
Payless Co and they fit perfectly. My wife kept saying how I could pass
for a woman anywhere.
I spent the two weeks leading up to the party practicing walking and
other female mannerisms such as sitting and I also got where I could
apply my own make-up pretty well. I spent most of my time at home
nights wearing female clothes and getting accustomed to being a woman.
I was starting to feel natural dressed and even started to wear panties
to work under my clothes. At first I was wearing some of my wife's but
she later bought me several pairs of my own. I felt a strange warm
feeling when I carefully placed the new panties
in a special drawer where I kept my lingerie.
My wife had been
stopping by a second- hand clothing store and picking up dofferent
articles of outer clothing for me to try and soon I had several skirts
and a couple of dresses. She finally ended up dresssing me in a very
short skirt and pretty white low-cut blouse. She let me use her breast
forms to put in my bra. I strutted around the house looking very much
like a sexy little tramp.
One night I had removed my outer garmets and was laying across the bed
in stockngs, bra, garter-belt amd panties. I had arrived at the point
where I never wore male underwear and I was starting to hate taking the
other things off too. My wife came into the room and lay down beside me
and started to mess around. Before I realized it she was fondling my
penis through my panties. We ended up having great sex with me dressed
as a woman and we haven't stopped doing it since. We won the door prize
and now have a new 27 inch TV which cost us practically nothing. I have
continued to dress and have even lost enough weight to enable me to wear
size 6 panties. We ordered a new pair of breast inserts and my wife
insisted on the big ones (D cups)..They cost a lot but you should see
the guys look when I wear tight blouses as they bounce and look very
realistic. We now go out together dressed as two woman and have a great
time . When we get home we usually have wild and very hot sex as my wife
really gets turned on by my lingerie. I ordered a voice training tape
from a TG site on the web and it has really worked as my voice is
sounding more and more fem as I practice.
I don't know where this will all end but I now wear panties and
stockings to work under my clothes and I even wore my bra one day
(without the inserts of course) My eyebrows are plucked and I do have
some people notice that but I am having too much fin to care!!! Take it
from me guys, try it you'll have much fun and it may get you a lot of
good head too.
My wife is helping me keep myself clean shaven and my eyebrows plucked.
I have been using cosmetics to soften my skin and keep it supple.
Doing my own make-up has gotten a lot easier but I am finding out it
takes a lot of time to be a woman and I spend a lot of time with my hair
now that it has gown down to my shoulders again.
I once felt a little inferior for being such a small guy but now I am
happy about my small feet and small boned frame as it makes me very
passable now that I am getting the voice . I go out fully dressed with
my wife and the clerks never quiestion me when I want to use the ladies
fitting room. My confidence has grown by leaps and bounds because of my
voice change and that 30 dollar voice tape was a great investment.
I wish all men could feel how sexy and comfortable panties are and I
think they would all want to wear them. When my wife has sex with me
she loves to massage my penis through the lingerie and will even nibble
on it at times . I am on cloud nine when she calls me her little
"whore" and little "slut" as she takes me with her big dildo.
When I
am dressed my penis stays semi-erect most of the time so we are really
having a lot of sex now both at home and with other swap friends.
My wife recently fullfilled another one of her fantasies when we met
with our first black couple. They were both beautiful black people and
he has the largest cock my wife has ever encountered. She dated one
black guy in college but she was having her period and all she could do
was perform oral sex on him a couple of times. He left that school
before she could have intercourse with him and has always been curious
about it. A few days ago she got her chance and she performed
beautifully while his wife and I watched. He took her mouth first and
I could not believe how much she deep throated. This guy is over 11
inches and she took all but about an inch down her gullet. When he came
he shot directly into her stomach which was a first time sight for me.
After a short pause he took her annally and that was one of the most
erotic sights I could have imagined and as I watched that massive penis
dissappear I could not believe my eyes. I was glad no strangers could
hear as she was screaming and carrying on from the mixture of pleasure
and pain. As he later took her in the normal manner it was almost an
anti-climax.
He was not BI so I only had his wife to play with but I really would
have liked to try that big penis on for size. I hinted at it but he was
straight and wouldn't consider it. I had to settle for my wife's diido
when we got home. Her ass was sore for two days or so after taking that
giant reamer. We plan to make them a regular treat as my wife is
addicted to that big cock of his. I got some great cam shots and we
watch them as we have sex. If you choose to post this next month I
hope some of your readers will send in their comments. We have given
your website info to several of our swinging friends and I hope they
write you.
We met our first couple on the web so we tried again and had so many
replies we really didn't know where to start but decided to go with the
ones closest to our location. Over a period of about ten days we met
several other couples personally and finally decided on 3 . My wife
loves heavy-hung men and that made our final decision. One guy pulled
his cock out in our car as we both were not convinced when he told us
how big he was. It was not the longest I have ever seen but it was
inbelievable in girth!! My wife went crazy when she saw it and wanted
to suck him in the back seat but his wife suggested better and we
planned a meeting.
It took some arranging of schedules and maneuvering but we finally all met
at our house one Saturday night and the party started. I wore very sexy
lingerie with my new fishnet stockings from the web which I had ordered
earlier. I went all the way in drag with lipstick and the entire works
and they were impressed. What followed was a night of sex and
debauchery we will never forget and it would take a week to describe all
that happened. My wife got her wish and was triple penetrated several
times during the night and I sucked and fucked until my neck was stiff
from the up and down action. Both our lips were swollen and puffy the
next day. My "pussy" was stretched and worked to new lengths especually
by the guy with the abnormally thick penis. It felt just like a hot
baseball bat when he shoved the 8 inch monster into my ass. He was so
thick neither my wife or myself could deep-throat him. The most
erotic sight was watching my hot little wife take 2 cocks into her ass
at the same time and as I watch her more and more I sometimes wonder how
far she would go?
Even though I felt like a woman my male equipment finally gave out but I
continued to use my tireless lips and mouth well into the wee hours and
finally started to doze while watching my tireless over-sexed wife
devour another cock while taking another in her ass. I was awakened a
litlle later by the big man taking me for the third time and as I looked
around I realized only he and his wife remained. As he pounded me over
and over I still felt a luttle pain but knew I had reached a point where
I would be needing a lot more in the future. As I watched my wife's
head buried in his wife's pussy I knew she was now a dedicated swinger
too.
Readers who are thinking about swinging
don't know what they are missing if they don't try it..... Just my
opinion.
I'm sure some people would consider us very perverted but so be it as we are
having too much fun to feel guilty. I now have a great female wardrobe
and wear panties and stockings and often bras to work. We keep my body
shaved and she has even plucked my eyebrows now. I wear female slacks
and blouses to most places I go. I don't wear the really fem kind but
they are fem never the less. I have female shorts and I wear stockings
under them as well as female sandals. I buy my own things now and have
found a couple of places that let me try dresses and other things on
before I buy them. I love to watch the faces of the clerks when I tell
them the frilly panties and things are for me. I am getting better and
better at changing my voice and have really practiced female walking and
other mannerisns. I am fortunate in having a very small frame and
feminine features which I get from my mother. I have lost weight and now
am wearing size 6 panties which are about the same size as my wife's. I
plan to get even smaller as clothes are a lot easier to buy when your
small. I am starting to go out in full dress now and I guess I am
passing as no-one seems to suspect. I even visited my doctor (She is a
female) wearing panties and she saw the frilly pink tops over the
waist-band of my female slacks and never said a word. She is also my
wife's doctor too and so far has said nothing to either of us.
Our last few weeks have been a whirlwind for us both and we are enjoying
every minute of it. My wife enjoys living with me as a woman and says my
disposition is better. I would love to hear from other men or women who
share our life-style so I hope they will write you. My new female name
is "Kris"
In the last 3 or 4 weeks much has happened to me and I am now a
full-fledged cross-dresser with a pretty good wardrobe. I have just
experiened my first BI experience where I was fucked several times by a
horse-hung guy that we contacted on the web. He is married and his wife
introduced my wife to the joys of bi-sexuality and now she is a devotee.
He also helped us to live out one of my wife's long-time fantacies which
was to be taken by two men at the same time. As I watched him take my
wife the first time I was a little jealous as she seemed to be enjoying
his huge girth and length better than my smaller penis but after I took
his wife a couple of times I felt better. Later as he mounted me I was
very glad my wife had pepared me with the dildo as even then I felt a
little pain for awhile.
Having another penis in my mouth was the strangest thing I have ever
done and many emotions flowed through me as I attempted to adjust to his
huge size. I have watched my wife devour my seven inch penis hundreds
of times and I really never gave her credit as it takes stamina to
continually suck for ten or fifteen minutes. Swallowing was also a
little tricky too but I managed to get most of it down. I know I was
not very good at it the first ime but after 4 or 5 times I really
started to enjoy it.
Strangely
enough I am not very BI until I get dressed in fem clothes and then I
seem to step into the role. Being dressed in lngerie seems to keep me
in a continual state of readiness and I just could'nt seem to get enough
of this guy and we both left their house sore and well worked over. We
are arranging another meeting with them right away and they are inviting
two other BI coupes to join us.
To people who have been indulging in the above things, this may not seem
like anything special but to us it represents a whole new horizon. As
we watched tapes of our week-end I had to marvel at how fem I looked on
my knees as he took me just like a female. The tapes really turn my
wife on and she just watches them over and over,especially the one that
shows her being double penetrated. She now wants to try 3 men at once
and I guess she will experience that at out next gathering, I want to
try 2 men at once
myself
To think this all started with just a dildo is amazing to me and who knows
how far we will go in out next little get together. I know I am
throughly enjoying the feel of my cleanly shaved body in panties and
bras!!!!!
I was a little embarrassed at first but since then I have been wearing a
bra and stockings with a garter-belt and my wife has purchased several
new items of female clothes including several pair of lacy, silky
panties which I wear everyday now. She has shaved all the hair off my
body and I can't believe how good it feels. I really got brave and have
been wearing my panties and stockings to work a couple days a week. I
even wore shorts to the mall with sheer thigh stockings and I don't
think anyone even noticed. We visited 'Payless Shoes' and I bought 2
pair of women's shoes and have been practicing walking in high heels. I
also bought a pair of women's open toed sandals which have a slightly
raised heel. As I was trying them on a woman walked by us but she just
smiled and kept walking. When I took them to the counter to pay for
them the clerk never batted an eye as she opened the boxes to check them
but when I left she smiled and said "Have fun ! My wife had gone to
the car as she wanted my to get accustomed to buying my own things.
When we got home I dressed in stockings, garter belt and bra with my
high heels and started to practice walking.
My wife was so turned on
she put on her monster dildo and soon I was face-down on the bed and
getting my 'pussy' reamed good. I have never seen her get so aroused
as when she has me in drag. She can't explain it herself but says whenshe is fucking me she has this feeling of power and she climaxes several
times during her 'rape'. When she hits my spot in my ass it is a
feeling like no other and I can't lay still and usually start to squirm
and this turns her on even more. She calls me 'whore' , 'slut' and
other things and tells me how good my 'pussy' is . I get so turned on
now that she usually gives me a blow-job later and they are mind
boggling climaxes for me.
She has been letting me wear one of her wigs and since I am very small
of statue for a man I really could pass for a woman, I think. She has
been doing make-up on me and we are going to a second-hand women's
clothing store this week to buy some dresses. She called the lady who
operated the store and she said she doesn't mind if I try them on first.
She told my wife she sells a lot of women's things to men. My wife
talked at length with her and we feel like we know her already.
We have always had good sex with anal and oral a large part of our sex
life but our sex has become so much better now. My wife loves it when I
take her dressed in lingerie and I am loving the feel of female clothes'
especually the panties and stockings. I now sleep in sexy gowns and
panties and my wife can't keep her hands of me. I have been awakened
several times by her sucking my penis while she rubs my butt through my
silky panties. I have also grown to love the big dildo and even though
it still hurts a little at first she can get a lot more aggressive now
and really pounds it into me. Knowing she enjoys fucking me so much
gives me a thrill and I love to have her enjoy me this way. I once
wondered how men could wear women's clothes but now I see things
differently. I don't even like the feel of men's things anymore and I
plan to stay in panties from now on. Seeing the joy and lust on my
wife's face as she takes me on my back with my legs in the air is a
sight I can't describe. I look up at my stockings and garter belt and I
realize I am really starting to love being a "woman"
I would like to encourage men who have never been penetrated by a woman
wearing a dildo to try it. You may not want to wear women's lingerie but
you will never forget the feeling that having your "P" gland rubbed and
I think you will want more !!
I will write again in the future to let you know how my 'female' life is
progressing. We are thinking about meeting couples in similar situations
and comparing notes so life should get even better.
She has always been enthusuastic about sex but lately her mind has been
working overtime and she wants to try a lot of the things we read about.
We started enjoying anal sex which eventually led to her taking me with
a dildo as well as me fucking her annally. She had done annal sex
several times before but she had to stretch me quite a bit before I
could handle the first dildo she used on me. When I was at the point
that I could take most of the first dildo without a lot of pain she
suggested we get a larger one. I could not find one locally so I asked a
friend of mine who is a commercial pilot to pick me up one on one of his
flights to Amsterdam. When he handed me the large box he grinned and
told me to have fun. He is one of the few people who know about our
little experiments in the bedroom. My wife will not admit it but I know
she has the hots for him.
This dildo is a monster and I was very apprehensive about her using it
on me. It is 12 inches long and almost nine inches around and is very
realistic looking wth a very large head on it. My wife quieted my fears
some when she said she would stretch me a little more before using it.
She started to really use the smaller dildo on a regular basis and
nearly every night she would ream me good and afterwards would shove as
many fingers as she could into my "pussy" as she started to call it.
Over a period of several weeks she has really inlarged my opening and
last week we decided to try the "monster"
My wife spends a lot of time on the net talking to other females as well
as men and she usually tells me about the really 'hot' comtacts she
makes . She has been talking to a Dominatrix for some time now and I
think the idea of being in control has become very interesting to her
and I like the fact that she has become more agressive in sex matters.
We had planned my night for several days and I first took a good enema
which we always do before annal sex. I was laying on the bed nude when
she walked into the bedroom wearing the huge dildo. It was so heavy the
harness would barely hold it and it hung down almost to her knees. It
looked even larger now and I was very nervous. As she rolled me onto my
stomch she squeezed a large amount of KY into her hand. She forced four
of her fingers into my now well stretched opening and spread the jelly
all over my hole. Soon she had her small hand inside me and was
tickling my postate. It is a sensation like no other and I started to
squirm on the bed and move my ass trying to make the feeling last. I
was now so turned on I would have let her stick anything in me. She
leaned over and whispered in my ear telling me I was her 'little girl'
tonight and she had bought me something . She wiped the lube from her
fist and walked to the dresser to get a sack laying there. When she
took the items out I thought she had bought them for herself as there
was a pink pair of panties and a short babydoll gown. I was so wrong!!
They were for 'her new little girl' as she put it and she told me to put
them on. I hesitated at first but was too aroused to put up much of a
fight.
When I pulled those silky panties on I can't explain how I felt! I was
a little embarrassed but they felt great, much better than my shorts. My
cock got hard instantly . Soon I was on my knees wearing the sexy
baby-doll nightie waiting to be taken like a woman. My wife kept telling
me to relax as she nudged the opening with the head of the huge rubber
cock. As the gigantic round knob burst through the ring of my ass I had
expected lots of pain but due to the preparation we had made I felt very
little and my wife was encouraged and soon had about seven inches inside
me and had hit my postate. It was great from there on in and soon she
had all but a couple of inches inside me and was really starting to fuck
me. My panties were down around my balls and I reached back and felt the
silky material as it carressed me there. My wife pinched me nipples
through the baby-doll as she worked the mighty shaft in and out of my
'new pussy'. She leaned foward and started to talk to me calling me
'whore', sissy and other things, asking me how it felt to be a female.
Readers, I can honestly tell you that I have never been so turned on by
anything and I actually came as she fucked me. I filled my new panties
with juice and soon she pulled out with a 'plop' and I ate her to an
earth-shattering climax. We lay for several minutes before either of us
said a word.
I realize this is a long story and I apologize but I want to tell amyone
who reads this that if you are the least bit interested in what I have
said, please try it!! You will never be sorry. I wrote the Domina that
prompted my wife an email thanking her for encoutaging my wife to try
this. I now have several new pair of panties and she us getting me a
bra so our fun is only startting.
Later on and to this day, I still go into my sister's
room and take some of her satin stretch panties and
some of her rayon and satin dresses out of her closet
to wear in my room. I like imagining that I am a girl
and that I am being tied up and raped. I love the feel
of the material on my body.
I also sometimes think of swallowing my own cum, but
by the time I masturbate, I am not horny, and I won't
attempt it. I also fantasize about sucking cock, but I
am not gay. I think that I am just curious about these
things.
A common crossdressing fantasy - but it does happen occasionally JEL
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