Sissy Weddings

satinmarabana

Really Really Experienced
Joined
Mar 27, 2009
Posts
323
Okay, I just had a call this morning that I'll put at the top of my "unusual" and "unexpected" calls lifetime list. A former male lover, who I'll call Jane (for good reason), called me this morning to ask a really big favor. He was my second sissy lover and we'd parted on good terms so I enjoyed catching up with him.

Well, it seems that he'd really explored his bisexuality and gotten into a serious relationship with another man, a sort of regular-looking fellow, not another sissy. As you could guess, there is a sort of dom/sub angle to their relationship but not in any deep, serious way... more a result of their personalities. Jane likes to be female in the relationship which he indulges by working from home as a technical writer.

They plan to get married now that Vermont has legalized gay marriage. This has unleashed a deep and passionate response from Jane about the wedding. He is consumed with all of the 'traditional' experiences of the bride and wants to experience everything.

So Jane asked if I would be his maid of honor and help him. Although the thought of the time it would consume over the next couple months made me hesitate, I agreed. A once in a lifetime experience I think. :)

This weekend he... no, she (more natural that way) is coming down to spend the weekend and we're going to try to get ourselves organized. I'm also calling around town to find a bridal boutique who will be open to accomodating her since finding the bridal gown is the top of her list.

I'll try to post updates here, but I was curious if any sissy had done any of this or if it was a common sissy fantasy?
 
my girlfriend tells me that when we get married, we might need to buy two dresses. I tend to agree, I have fantasized about being the beautiful blushing bride, but at the same time I don't think I could spend my life with a guy. So... My situation is a little different. But yeah, I would love to be a beautiful bride.
 
"I now pronounce you Man and Sissy. You may kiss your bitch."

That is like, so fucking hot. Think you could post some pictures of the wedding? I'd love to see a sissy bride.
 
I definitely will ask her if she'll let me. I know she's thinking of a private ceremony and hasn't found a church that will marry them this way.
 
Sorry for the long delay in posting. Helping Jane has been time-consuming since she wants a June wedding. We did have our day gown shopping and I have to admit it was a big success if I do say so myself. :)

We started the day at my apartment where my daughters met Jane. (They are aware of their father's cross-dressing so it isn't something abnormal to them so they were very sweet with Jane). One of them cooked us a light brunch as we discussed what I was planning.

I'd made contact with a manager at a David's Bridal who was very sympathetic to Jane's situation and I'd made an appointment for late in the day when we could have some privacy. The manager was going to keep the store open late for us.

We stopped at a stationers to look at announcements and a spa for mani/pedis a girl talk. (Jane has better nails than I do, the bitch! ;) )

As a surprise we stopped at a designer shoe boutique. Jane's fiance' is well off so between the two of them, she wasn't worried about prices.

I guess I should explain that Jane wears her hair in a cute sort of androgynous style, short and styled. She was wearing women's jeans, a women's blouse, and short heels along with carrying a little clutch. She doesn't really pass for a woman visually, but she is so comfortable and practiced in her voice and movements, that people accept her as female more often than not. I give her credit, she's come so far since we were dating.

Anyway, we killed two hours in the shoe boutique, trying on everything our hearts' desired. She bought me a pair of open-toe, cross-strap 3" heels in black patent leather as a thank you gift while she bought three pairs of sexy high heels in gold, black, and pink. (The girl could never resist pink).

Arriving at David's Bridal, we met the manager who had us wait in the plush seating for the last few minutes the store was open. After the last female customer was escorted out, the manager, Sydney, explained that her staff had volunteered to stay and help us out. I already know that DB provides brides gracious attention (it's where I bought my dress back when) and this was even better.

Jane stripped to her bridal lingerie and added the breast forms she planned to wear. They were D-cup breasts which really looked sexy on her frame. Her lingerie was all white satin: bra, panties, garter belt, and white silk stockings with a simple garter.

I sat back as Sydney and the other girls led Jane through the different styles to help narrow down what she liked. She was focused on dresses that would cover up her bra which she had to wear for her breast forms. (she has a bad skin reaction to the adhesive I've used with other sissies) But she fell in love with (hope this link posts correctly

http://www.davidsbridal.com/webapp/...tegory=-49999486|-49995498&catentryId=1000209

It is style L9606 at davidsbridal dot com if that didn't work. The girls helped her find a low-back satin bustier that would support her under the dress and give her that sexy bare back look with the dress. Jane ordered a white version of the bustier (they only had ivory in the store to use for tryons) and the dress.

We had a couple drinks and took a taxi home around 8pm and I encouraged Jane to gush about the experience to my daughters who gave her the perfect all-girly wedding-crush experience.

I'll admit that I felt the old urge to take Jane to my bedroom and put her through her paces but I didn't say anything. She's with someone new now and I'm happy for her, and a little jealous. She did give me a lingering kiss before she left to head back home.

There is a lot more to plan and Jane tells me that she has ideas on what she wants her bridesmaids to wear. I've not met the other bridesmaids so that should be a very interesting experience.

Kisses
Satin
 
It really is. We're going back soon to have it tailored for her. Wedding is only a little more than a month away.
 
I met Jane's bridesmaids last night.

Collette is a tiny woman but very sweet with a great sense of humor.
Stephanie is about Jane's height (~5'8" I'm guessing) but rather... statuesque. We'll certainly make a remarkable group standing up with Jane.

We all went out for drinks and to talk about the planning. I was pleased to learn that both girls had been friends with Jane for a couple years and were proper girlfriends, helping Jane with her shopping, makeup tips, the right hair styles. Very supportive and I could tell that Jane treasures their friendships. They were telling all sorts of stories about shopping together. Stephanie and Jane can shop in the same stores while Collette tags along to give her opinions on things.

It became a sort of unplanned bridal shower when they insisted that I go with them to a little hole-in-the-wall lingerie shop called Heartline Lingerie. I was impressed with the variety of lingerie there. I guess it was more planned than I realized when the owner, a pleasant, heavy-set gentleman in his 50s, brought out a series of small gift-wrapped boxes for Collette, Stephanie, and me. Each one held a satin panty with either "Bridesmaid" or "Maid of Honor" embroidered across the tush. Super cute.

We went to have another drink at a local place and it just seemed natural to stop at a nearby Adult store before we called it a night. Stephanie and Collette made it their mission to get Jane to admit which dildo best approximated her fiance's cock. She finally fessed up that it was about 7" long. We went through their little lingerie selection, mostly to laugh at the bawdy inscriptions and crazy costumes.

Quite a night. I was very pleased to have met Collette and Stephanie. Next hurdle is the dress fitting and finding the place for the ceremony. We're looking at some parks up near where Jane lives now.

Kisses,
Satin
 
Well, girls, we're almost there. The wedding is set for this Saturday in the back yard of a friend of Jane's fiance'. We found a Unitarian Universalist pastor who was pleased to preside over the ceremony.

The dress fitting went very well, even with some other women stopping by to give Jane encouragement. Before it was over she and I were both crying, it was so beautiful.

I've got my maid of honor dress which is a blush pink and made of lovely rich satin (Jane's favorite). Jane made me promise to wear something special underneath for old times... our favorite strapon cock which happened to be neon blue. Not surprising considering how kinky she is. Part of me wonders if she has some sort of *special event* planned on Saturday... I kind of hope so, because that strapon isn't going to be comfortable for hours. My daughters will be with their Dad all weekend so I guess I'm free to be naughty. :)
 
thanks for the update...looking forward to hearing how it all turned out and about the after party ;)
 
I know, I'm really confused/concerned/excited about the possibilties. I've met "Matt" a few times and there hasn't been any tension between us, me being Jane's ex and all, but I don't want to assume anything either. I've already tried the strapon and it doesn't show under the flared skirt of the dress so if nothing happens, I get a little sore from the harness but that's okay if she wants it there for some reason. If something does happen... well, the mind reels with the possibilities and I'll confess I get excited thinking about it.
 
Wow incredible. I find this very interesting. I do look forward to hearing how this all comes about.
 
Well, here's how things worked out this weekend. At the pre-wedding dinner for the wedding party, I met the groomsmen. Nice guys and I cornered one when I realized that I could see the clips of his garter belt when he sat down. He admitted he was wearing lingerie and was a sissy. He'd met Jane first and then Matt and was a 'family friend'. The other two were Matt's brothers.

I helped Jane get ready for the ceremony and I didn't hear a word about the strapon I was wearing under my dress. She looked wonderful in the bustier and the dress. I'll admit I cried a little, more during the ceremony. A lot of love between them and I knew it was Jane's dream come true.

There was a small reception after the ceremony, held inside the house as it was threatening some rain. Wine and such was flowing freely as a couple more friends 'catered' all sorts of wonderful food.

Eventually, Jane took me aside. She gave me a quick kiss and I returned it, wishing her all the best in marriage. Her hand found the strapon cock under my dress and she giggled.

"So yeah, what was the big plan for this, honey?" I asked, dying to find out.

"I told Simon about you a long time ago and he's been wanting to meet you for a long time."

Bing! Light bulb turned on over my head. Simon... the sissy groomsman.

"So this is for Simon then?" I asked with an evil smile.

"Only if you want it to be. I didn't want to pressure you, but if you're interested, just tell him to 'go to his room' and he'll show you where you can get some privacy."

I've been clear on the boards here that I haven't had a lover in far too long. My dress felt great, I felt pretty, and I felt horny inside. Jane had given me just the present I needed. I gave her a longer kiss on the cheek and thanked her before heading off to find Simon.

More about that next...
 
Absalutely lovely story, I look forward to the conclusion. Though I am a bit jealous of the groomsman and jane.
 
Whew, finally have a few minutes. This is as best as I can remember it, forgive the paraphrases.


So I found Simon and gave him the password. He couldn't have grinned bigger as he showed me along a back hallway to the master bedroom. I closed the door.

"Well? Strip down sissy!"

He obeyed, revealing cotton panties, a garter belt, thigh high stockings, and a flat bra.

"Now are you a proper sissy?" He kind of mumbled an answer. I just raised the skirt of my dress to reveal the strapon. I swear he was about to faint.

I coaxed him, praising him for being such a pretty sissy, and pushing him to admit that he wanted to suck cock. It didn't take much, ha ha.

I let him suck on my strapon for several minutes, cooing and praising him. He tried to deep throat it but he needs more practice to pull that off. The harness was doing its job, grinding my panties against my pussy. Just watching this pretty man in his lingerie sucking my "cock" had me very excited.

I took him to bed next. He showed me where the lube was hidden and we started. He said he'd had things inside his bottom before but it took a long time for him to relax enough and take my strapon. I didn't mind. Gave me more time to play his headgame, praise him and entice him to reveal his sissy secrets to me.

At last it slid all the way in. He was very excited at that point and it was only moments after I got a good thrusting going that he moaned and came hard all over the sheets. I unbuckled the harness and tied it around his legs to push the dildo in him as he moved. I found a dry spot on the sheets and let him lick me. I was almost as fast as he was... I'd been saving up for a long time.

Wonderful night and he was very grateful for the experience. He asked for my number and I gave it to him... along with the night and time he was to be at my home for round two (while my girls are away). Time to teach him that sissies eat up cum!
 
I hope your new sissy realizes how lucky he is -- sounds like he's found a fine, fine mistress! I'm jealous! :devil:
 
It sounds like you found yourself a nice workable sissy. Hope you post stories about any other future encounters that you may have with him...:)
 
Glad to hear you finally had a much deserved release. I hope your sissy learns quickly that your pleasure comes first. Can't wait to hear more!
 
Hot, hot update. I'll bet your boy toy shot a huge load, his first with a strap-on drilled into his virgin ass.

How are you planning on making him eat cum? How about you have him dress up, lick your pussy while on his knees, then have him jack off and cum over your cock.

Then back to his knees to suck the warm sperm off your cock.

Thanks.
 
What a very lucky Sissy (or sissies including Jane too).

Your tale gives us all some inspiration and hope that we might also find a woman willing to accept us for the girly sissies we are satinmarabana. :D

It will be nice to hear more as things develop!
 
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(Again, the dialogue is paraphrased from memory)

I had to pull some strings to have my daughters out of the house again last night, but I had to have Simon over again. I'd dug out boxes of lingerie, frilly made-to-order sissy dresses, some light bondage, heels, the whole business.

I'll admit, we started very conventionally. It's been a long time since I've had a man the normal way and I needed that. Simon came through with flying colors, lasting until he thrust me into a great series of orgasms. I carefully preserved the cum in his condom.

Then we played dressup. Well we started as always with an erotic shower where I shaved him from the neck down. With care and using lotion, it took a long time, but he was baby smooth when I was done with him. I took the time to use a lubricant that I really like and use plenty of it in his bottom. I said nothing but he knew what was coming.

Then it was to the clothing. He was a little big for some of the items, but the stuff made for sissies had lots of elastic in the right places. Soon I had him in satin sissy panties, big with ruffles all over the bottom and a lace-ringed hole at just the right spot in the back (I LOVE ebay!). He moaned at how the satin felt on his sissy-shaved skin.

Next came thigh high stockings. I found a pair of nylons that didn't look stretched out and taught him how to put them on. I thought about squeezing him into one of my corsets, but I knew I wanted him sooner than putting that on would take, so I have him a very lacy, frilly garter belt.

A couple false breasts and a satin sissy bra and it was time for makeup. I didn't get into a serious 'teaching moment' there, but he enjoyed me talking about how sissy girls have to learn to put on their makeup.

I let him pick the dress, another made-for-sissy number with puffed shoulders, flared hem, petticoat with layered crinoline. I grinned as I felt him shiver in erotic heaven as I zipped the back of the dress up, trapping him in its delicious loveliness.

Lastly came the heels and he was ready. I took a series of pictures of him strutting for the catwalk and we were laughing a lot at how much he was enjoying it.

I was more than ready so I had him sit and watch as I stripped down, put on some black satin panties, and then strapped into my harness. I caressed the thick rubber dildo as if it were my own cock and looked at him with lust in every pore of my body.

"Alright, sissy girl, I gave you all the pretty clothes, now you give it up to me." (I remember it because I'd been thinking of just the right phrase to use.)

I forced Simon to his knees and made him give me a slow, erotic blowjob as I sat on the edge of a chair. I ground against him, working the ridged base of the cock back against me, stroking against the satin and getting me so wet. I got closer and closer to another orgasm and I ordered him to get me off, suck hard, make me cum. I started fucking his pretty mouth and just as I was about to reach my orgasm I pulled out and poured out his cum from the condom all over his lips and face and the cock. Then I shoved it back in and came hard.

(God I love sissies!!!)

When I came to my senses, I could see he was moaning in pleasure, overwhelmed and consumed by his fantasies as he licked cum off the hard cock.

Before he could clean the cum off his face, I pulled him to his feet and back into the bathroom. I urged him face down on the vanity, his body bent over at the waist and his cute ass pointed my way. It was here that I showed him another little "feature" of the dress. I took his arms behind his back and clicked simple hook and eye closure shut, binding his wrists together.

He was moaning and squirming now. I pulled up his hem and all the crinoline to find his satin-covered ass. I groped him a little, seeing the stain where the lube had pressed against the satin.

"You're all wet, sissy," I purred before yanking his pretty panties down to around his thighs.

I was pretty worked up by then and put a quick extra layer of lube on the cock and then pressed.

"Let me fuck you, Simon. Let me fuck you like the sissy you are so completely and deeply," I whispered into his ear. The cock slipped all the way in moments later.

"God you must love cock and getting fucked."

"Oh god yes, fuck me, fuck my sissy pussy," he begged me, writhing in his dress. I complied, getting a good thrusting rhythm going and enjoying watching the black rubber disapper and reappear from his tight, sweet ass. I thought we were going to last longer than the first time, but it had been such an intense night, it wasn't long before he cried out and coated the insides of his hanging panties with a huge load of cum.

I gave him a few thrusts for good measure, pulled out carefully and then helped him step out of the panties. I quickly presented "my" cum for him to swallow, licking the panties clean.

It was after midnight by then so we wound things down, cleaned up a little. He was originally supposed to go home after our 'date', but we sort of mutually decided he could stay and leave in the morning. He borrowed one of my nightgowns and a fresh pair of panties. I dressed up sexier than I do when I sleep alone and we snuggled to sleep. Even his snoring later that night didn't ruin it for me.

We'll have another date when I can arrange for privacy at home. Just don't know when that will be. Naturally Simon wants it as soon as possible, ha ha.

Well, girls, I hope you enjoyed the ring-side seat for me and my new sissies. I'm so glad to have found him.
 
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