Maid of Honour


As a transvestite, it had always been my dream to be a bridesmaid. My elder sister had known about my love of feminine things since we were tiny; indeed it could have been her love of dressing me up as a girl when we were children that influenced me in the direction of transvestism. So you can imagine how delighted I was when she told me that she was getting married and that she wanted me to be her chief bridesmaid. I had 'come out' as a transvestite to some of my friends and to my immediate family but there would be many people at the wedding who were unaware of my secret and who would discover it if I accepted this role. However the possible fulfillment of a dream was so strong that I threw caution to the winds and accepted her generous offer.

All the bridesmaids were to wear matching pale pink satin dresses and as chief bridesmaid mine was to be a little more flamboyant than the rest with extra bows and frills. I well remember going to the wedding shop to be measured and later to try the dress on and to have it adjusted to fit me perfectly. I wondered whether to wear male or female underwear when visiting the shop as the staff would be bound to see my undies. As I was to be fitted for a dress, I decided that feminine underwear was appropriate and I chose a pair of black control panties with extra padding round my hips and bum which would add feminine curves, minimize any masculine bulge and wouldn't show any slight leakage which was likely to ooze from the tip of my penis with the thrill of being attended by women intent on getting the fit of my beautiful dress just right. It was wonderful being treated as a woman and none of the staff at the shop expressed any surprise or other emotion at the choice of a man as 'Maid of Honour', so I suspected that I may not have been the first male bridesmaid they had supplied with a dress.

The day of the wedding arrived and I was very excited but also very nervous. One potential problem was toilet access. If I were to use the Gents, I would cause quite a stir but if I were to use the Ladies, I could be breaking the law. I decided to eliminate the problem completely by wearing a thick nappy and a pretty frilly pink satin rubber lined waterproof nappy cover over it in case anyone happened to lift my skirts. Also, although the bulk of a nappy would have been very noticeable in trousers, under the bridesmaid's dress, it simply enhanced my hips and bum giving me a more feminine look. As I had worn padding under my control panties at the fitting with a view to a more feminine look, the dress still hung perfectly.

At the church I received many complimentary remarks on my appearance and Janet, my sister, explained to those previously unaware of my transvestism that she thought I'd make a good bridesmaid and didn't they think so too, thus implying that it was her decision to have me dressed in such a delightfully feminine outfit. One or two expressed disapproval but overall the mood was favourable and I began to feel very relaxed.

It was about halfway through the service that I became aware that my bladder was becoming full and I thought how convenient it was that I'd decided on the nappy as otherwise I would have had to embarrass myself and others by having to make my way to the toilet and so disrupt the service. As it was I just relaxed and let my bladder empty into my nappy. It felt so deliciously naughty, wetting myself in a dress in public, that I got an erection which fortunately was sufficiently contained within my nappy that there was no unfeminine bulge visible at the front of my dress.

The other bridesmaids were all girls, ranging in age from 5 to 18, all of whom thought it a giggling matter to have a man as chief bridesmaid. At the reception, it was wonderful to be seated with the bride and groom at the head table and to be given a gorgeous bouquet of flowers for fulfilling my role as head bridesmaid. I said, "Thank you", and gave a little curtsey as I was handed the bouquet,

After the meal came the dancing and after the bride and groom had had the first dance, the Best Man invited me to dance; I was in heaven as I danced in the arms of a handsome young man, my skirts swirling as I twirled in time with the music. My partner's hands had been exploring a little more than I thought they should during our dance but I was so happy to be treated so thoroughly as a woman that I welcomed the extra attention, and when he suggested we go outside for a breather, I welcomed the opportunity to be alone with him.

It was dusk by now as he led me across the lawn to a secluded summerhouse in the woods. It was there that he told me that he found me irresistible and before I could comment his lips were on mine, his tongue was exploring my mouth and his hand was under my skirts. I was wondering what his reaction would be when he encountered the nappy but all he said was, "Ooh yes, a naughty little girl who wets her nappy. How utterly delightful!" The summerhouse was too public for anything other than fondling and kissing but he told me his room number (we were all staying overnight) and begged me to come to his room after the reception. I was a little doubtful - was I gay? - but the chance to be treated entirely as woman, even to the point of being fucked by a man, was just so irresistible that I acquiesced to his pleadings. I was in quite a state of anticipation as the reception drew to a close and we all retired to our rooms. Once I had made sure that the coast was clear, I made my way to Tim's room, not even taking the time to remove my (by now well soaked) nappy as Tim had expressed an interest in wetting fun.

He opened the door immediately to my tap and hurried me inside. Once again I felt his lips on mine and his tongue inside my mouth but this time it was a relatively brief kiss as he wanted to get under my skirts as soon as possible. He pulled down the waterproof frilled satin nappy cover and then carefully undid the safety pins before removing the sodden mass of towelling. It was only a moment as he dumped the nappy in the shower before he was under my skirts again. I soon felt his mouth sucking my penis which rapidly grew very hard, at which point he turned his attention to my bottom. I had never before experienced a tongue probing my anus but it was certainly a feeling I wanted to last and to repeat. I felt his lips surrounding my rosette as his tongue did its best to get inside, licking, pushing and probing, giving me the most exquisite sensations. If this was what being gay involved, then I was all for it.

After some time he emerged from under my dress with a very prominent bulge showing in the front of his trousers. By now I was willing to do anything and I immediately reached for his zip. I undid his trousers as quickly as I could and then lowered his figure-hugging spandex underpants to reveal his magnificent manhood which I couldn't resist taking into my mouth after dropping to my knees. A few minutes of oral manipulation were all he could stand before he pulled out and commanded me "On the bed on all fours!" I obeyed and there was a little struggling to free the skirts trapped under my knees to give him full access to my bottom. Once again I felt his lips and tongue on my rosette but then I felt an exploring finger work its way right inside me before I felt something much bigger and thicker than a finger pushing at my anus.

By now I really wanted him inside me and I pushed back in response. There was a moment of discomfort as I felt my sphincter yield to our combined efforts and it was a glorious moment as I felt him slide inside me, inch by inch until I felt his pubes against my cheeks. A repeated slow partial withdrawal and reinsertion then began, giving me tremendous pleasure from the sensations in my anus and rectum. This slow fucking rhythm continued for about fifteen minutes before his excitement got the better of him and his tempo increased. I was in heaven and had no idea that the pleasure could reach even greater heights but as his thrusting became more urgent, I found myself involuntarily tightening my sphincter until with a couple of final deep thrusts and a long "Aaaaahhh", Tim pumped me full of his love juice at which moment I too spurted a large quantity of cream onto the bedspread. I didn't want him to pull out but he softened and with a slight plop I felt his cock slip out of me soon followed by a trickle of his cum which ran down the back of my balls. Being well and truly fucked by a handsome man who really fancied me was by far the high point of the wedding and we've agreed that we want to repeat the experience as often as possible.

It's great to have found a man who appreciates my transvestism and enjoys treating me as a girl in every respect.

Report Story

byTVJoanna© 4 comments/ 66404 views/ 18 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartkitten_tease, appifiable and 16 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (4 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (4)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: