Sissy Weddings

Oh god, that was incredible! What I wouldn't give to be Simon for a night...

I think he's going to be coming back. (blush)

What a hot story. I was wondering how you were going to "introduce" your sissy to cum. Pouring the cum all over your dildo from the condom really got me off. Satin you are sooo hot! Please keep posting.

Thanks for the super hot story. You really know how to fuck your sissy. Love how you saved his cum and had him lick it off your cock.

You do know you gave him the hottest night of his life, don't you? He'll always remember, and get stiff and hard, about his first time being a sissy bitch.

Now I need to go and read your tale again, this time jerking off with my soft, black satin panties.

neon_noodle said:

Thanks for the super hot story. You really know how to fuck your sissy. Love how you saved his cum and had him lick it off your cock.

You do know you gave him the hottest night of his life, don't you? He'll always remember, and get stiff and hard, about his first time being a sissy bitch.

Now I need to go and read your tale again, this time jerking off with my soft, black satin panties.

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Good girl!

All I can say is WOW!

Thank you Satin for sharing this with us. I hope I'm lucky enough to read about the next visit from Simon.

Okay, girls, Simon came over last night for a date. It was spur of the moment, but as soon as I knew my girls were going to be sleeping over at friends' houses, I called him and he drove down, probably breaking speed limits the whole way.

He had two surprises for me. He'd shopped at Frederick's of Hollywood and was wearing this under his pants and shirt: http://www.fredericks.com/Marilyn_Chemise/44572,default,pd.html but even more than that, he'd bought his first breasts. They weren't perfect (I wouldn't say that to him) but he was so turned on cupping them and caressing them inside the bra that was holding them... I'll have to get him set up with a good way or a good pair to adhesive to his chest so he can look better in the sexy outfits he tells me he wants to wear.

So he was very excited and I had to slow him down. We went to my bedroom and I made him undress me after he undressed to his lingerie. After he'd done that, I had him pleasure me with his tongue and lips which I happily drew out to about thirty minutes and several orgasms.

By that time, he deserved his reward. I held out the condom to him and didn't have to say a word. He put it on and jerked quickly until he came and filled it up with hot cum. He handed it back to me after I had my strapon on. I rolled up his slip-dress and pulled down his panties. I quickly lubed his bottom and placed the cock at his opening. I told him to push back on it at his own rate.

It took awhile (he isn't doing regular anal discipline so he doesn't open easily). But after a few minutes I had the pleasure of watching his ass descend down the thick shaft as he speared himself. I told him to fuck himself and held myself still. It was so hot watching him push back on my hard rubber cock again and again, hard! Exciting enough that I eventually grabbed his hips and began to fuck him.

He was whimpering in pleasure but coughed and asked for the condom back. I gave it to him and he pulled it back over the head of his cock. I sped up my fucking him and he quickly added another big load of cum into the condom.

I pulled out and made him kneel. I pushed the cock into his mouth a few times and then pulled out to leave the cock tip against his lips. I lifted the heavy condom over him and let the cum drool and splatter over his face. He lapped at it eagerly as I painted his face.

I sort of lost my aloof role and I knelt with him, licking the cum and kissing him, sharing it back and forth. It seemed like the most erotic and natural thing in the world to do with him.

We had intercourse a little while later although he had to stay in his lingerie as he fucked me. We used another condom and I had him swallow the last load all down after we were done. It was 2am when he kissed me and headed out to his car. I made him go wearing only his lingerie, knowing he'd love the thrill of it with very little chance of being seen.

Oh, that is so hot Satin -- that sissy of yours is the luckiest gurl in the world!

Had fun looking through Victoria Secret...imagining wearing different outfits for you. Love the way you are training your sissy to be a cum slut with the condoms. Have you considered introducing your sissy to anothers cum? Perhaps if you had a male slave?

Another super hot update. Thanks.

As an idea, and to better train your sissy, have him cum in a condom, then lube his ass up and give him a good fucking. When he can't take it anymore, pull the strap-on out, and drip his own cum all over the head of your cock. Tell him "I'm gonna cum in your ass Sissy. Are you ready to have your ass wet with cum, to feel that load blast into your tight hole, making you a complete slut?"

Then press the cum wet head of your cock into him, taking another part of her virginity - sticky cum in her ass for the first time. She'll probably blow her load as soon as that sticky cock slide inside and stretch her apart.

I'd love to give your Sissy her first taste of cock. I'd dress up in my sexiest outfit, my school girl slut look. Fishnet stockings, garter belt, black satin panties, short, slutty red plaid skirt, tight top with a stuffed bra, nice makeup and perfume, and my whore 3-1/2" high heels.

You and your Sissy would come over to my place, your Sissy all made up and dressed already so she would ride over all nevous about being stopped or recognized. You would come in, and I'd welcome you in, your Sissy stopping in her tracks at the sight of me all done up, stiff cock tenting out my skirt obscenly.

I'd lead her to the bedroom, her eyes, staring at my long legs and stockings, then you'd guide her down to her knees, ready to recieve her first taste of cock. I'd have her lick my fronm toes to the hem of my skirt, then make her bed to lift it up to see my cock.

The sight of my purple, swollen, throbbing cock, already dripping out pre-cum would make her gasp, while you took control of her head and moved her, mouth open, to cover my cock with her lips.

It would be the culimination of a lifetime of her fantasies to be dressed like a Sissy slut, on her knees, bobbing her now cock-christened lips over the warm skin of my meat, worshiping it with her body.

You'd be calling her all the names she knows she is, slut, whore, tramp, sissy, bitch, as she worked me in her mouth. I'd want the pleasure to last as long as possible, but I'm a slut myself, and the feeling of being all dressed up, being sucked off while you watched would soon be too much for me, and I'd groan as I splattered the biggest cum load of my life into your Sissy's mouth.

She'd be a good little slut and try to swallow as much as she could, but so much would be pumping out that my cum would drip out from her lips and smear down her chin, and over her top. Finally, I'd pull my cock out and smear my still warm cum all over her face, letting her lick it off my head.

l2btd said:

Had fun looking through Victoria Secret...imagining wearing different outfits for you. Love the way you are training your sissy to be a cum slut with the condoms. Have you considered introducing your sissy to anothers cum? Perhaps if you had a male slave?

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Haven't thought about that yet. We have a long time to enjoy just us for now. Maybe someday.

neon_noodle said:

Another super hot update. Thanks.

As an idea, and to better train your sissy, have him cum in a condom, then lube his ass up and give him a good fucking. When he can't take it anymore, pull the strap-on out, and drip his own cum all over the head of your cock. Tell him "I'm gonna cum in your ass Sissy. Are you ready to have your ass wet with cum, to feel that load blast into your tight hole, making you a complete slut?"

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That does sound hot. I'll definitely try it next time. Thanks!

I'd love to give your Sissy her first taste of cock. I'd dress up in my sexiest outfit, my school girl slut look. Fishnet stockings, garter belt, black satin panties, short, slutty red plaid skirt, tight top with a stuffed bra, nice makeup and perfume, and my whore 3-1/2" high heels.

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I've never had two sissies together before. Sounds very hot. I'll have to think about when and who to introduce, some day.

......

PT-NH said:

Wow - might be time to move this continuing adventure into a new separate thread ! The follow-ups have made me forget about the how it started as the wedding thread........
Thanks for sharing !!!! very exciting !
All of a sudden I feel like going to put on my black lacy panties and stockings under my work clothes for the rest of the day........

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As well you should!

I heard back from Jane today and life is good for the married couple. Sex is still great and she's really settling into a femme routine.

Simon and I had a date last night. The girls were home so I couldn't have him over, so I splurged for a room at the Courtyard by Marriott. I waited in the lobby even though I'd called him with the room number already. I wanted to see what he looked like.

Well, he got some big stares from the man and woman at the reception desk as my glorious little sissy showed up in brand new high heels, stockings, and a big trenchcoat. She walked a little wobbily to the elevator, waited for it to arrive as the others watched. Simon was glowing red with embarassment. He got on and went up to the second floor.

After a couple minutes, I put down the newspaper I'd been pretending to read and walked up the stairs to the floor. Simon was there outside the room with people walking by him when I walked up and gave him a deep kiss as a reward. My hand snuck inside his trench coat and felt his rock hard satin wrapped cock. He was loving it.

I unlocked the door and we went inside. He dropped the coat to show off a full sissy dress, complete with petticoats flaring the short skirt and a surprising bust. At first glance it looked like he had real breasts.

I was amazed and wanted the whole story but she knelt down, put her hands behind her back and bowed her head. I was disappointed that I hadn't thought to bring a more elaborate outfit for playtime, but I stripped down to satin panties, satin bra, thigh highs and heels. (The panties have little garters down to the stockings). Then I quickly stepped into the strapon harness and fixed a nice big cock against my pussy.

(Paraphrasing from memory...)

"You little cock-sucking slut, look at how femme and sissy you are! You're just a sex toy wanting to be used, to service hard cocks, isn't that right?" by now all Simon could do was whimper. I had to slow him down or he'd explode in his pretty panties.

I put the condom on his cock, careful to not stimulate him too much. I'd wiped off his precum and rubbed it against his lips, noticing the rich lipstick he'd used. I saw that he was shaved everywhere, nice a smooth. I slipped his wrapped cock back into the panties and sat on the chair in the hotel room.

I pulled the strapon to one side and my panties to another. Simon quickly came and used his tongue and lips to pleasure me. He's gotten very good at it. I'll admit that I fantasized a bit that I was with a real other woman and that made it even more intense.

After three or four waves, I pushed him back and reordered myself. I stood and began to stroke my own strapon cock lewdly. He didn't take his eyes off of it. "Sissy want to suck big cock?" Her answer was to begin, slobbery and noisy. Once again I wished I had a real cock to feel all the sensations Simon was giving me.

As she sucked, I slid a hand down into her panties, jerked a couple times and felt her cock throb and pump cum into the condom. She almost screamed in pleasure around the big cock in her mouth. I left the condom on.

After awhile of this, I wanted her ass. I had her stand and then spread her feet apart until her ass was at just the right height. She grabbed the edge of the desk to steady herself as she bent over ninety degrees.

I enjoyed flipping up the layers of her dress and then playing with her satin panties on her ass. Finally I had them pulled down enough to start lubing her with my fingers. I made plenty of time to feel up her breasts through the front of her dress and I was very excited at how real they felt. Simon had glued them to his chest.

I had him beg for his fucking, beg for big juicy cock, profess his love for being sissy, etc. etc. It always excites him and I feel things get more intense to me too. Soon, I was buried in his sissy ass and we were off to the races. He filled the condom a second time as I fucked him, groaning in his pleasure. I didn't happen to orgasm during this part but got to where I was ready to stop.

I pulled out and took off his condom. I ordered him to lie on the floor on his back. I knelt down over his chest (those breasts were in the way!!) and laid the cock to rest its tip against his lips. I started to jerk the strapon, "masturbating" for him so I could "get off". I felt his hand in his panties stroking fast. I played it up, moaning and grunting, then finally tensing still before splattering his lips and the tip of the cock again and again with streams of cum from the condom. He confirmed later that that moment made him cum again.

It was a great time, but I didn't realize that I still had unsated needs. As soon as he licked my strapon clean, I needed him. I wanted something in my bottom with such intensity, I was really surprised. We'd just worn out his cock, so he put the strapon on himself (to start).

We used lots of lube and when it slid in fully I moaned. I'd honestly forgotten how much I love anal sex. The hard cock wasn't as nice as a real cock, but that's what we started with. I felt his strong hands grip my soft hips and he started thrusting. I gripped the sheets hard.

After a couple minutes, he pulled out. I protested and then saw that he didn't need the strapon any more. His warm hard cock felt great. We went at it for quite awhile with me rubbing myself to a couple orgasms. Finally he came in my bottom and we both sort of collapsed.

I really wanted to get him into a pretty nightie and sleep with him, but I had to go back home. Had that delicious, not walking quite the same feeling this morning.

Wow...very nice date. Just lovely....

I'm really enjoying having a Sissy Toy again. Wish I had more time with him than our 'dates' but that's a great place to start.

satinmarabana said:

I'm really enjoying having a Sissy Toy again.

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*sigh*...

Well, it was too good to last. Simon broke it off with me with profuse apologies. Appears he has a steady girlfriend who has been suspicious about his trips to see me. I don't know the details but it sounded ugly. He was quite upset.

I'll miss him but maybe my sissy fixation is getting old. I've got new horizons to conquer...

Sorry to hear about your Sissy breaking off his sex romps. He may be back, you never know, as the desire for Sissy sex can be stronger than normal sex.

Maybe you should start a les phase, and pop that same sex cherry. It's not like you still can't use your strap-on, and give a slut a good fucking.

Well, you might be right, although I'm trying to be mature about it all. Going out to a dance club in Toronto was kind of crazy and I can't afford to take risks like that. I AM going to see if that hostess at the restaurant is a possibility. So we'll see...

yes it is a common sissy fantasy , i dream of getting married in a beautiful white wedding dress , i have already bought one ,i just need the right man to agree to marry me ,i am looking ,lol.

satinmarabana said:

Well, it was too good to last. Simon broke it off with me with profuse apologies. Appears he has a steady girlfriend who has been suspicious about his trips to see me. I don't know the details but it sounded ugly. He was quite upset.

I'll miss him but maybe my sissy fixation is getting old. I've got new horizons to conquer...

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Is there a opening then?

satinmarabana said:

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?

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i have never done it but it is a common fantasy among sissies and many places that offer a dressing service provide the wedding experience complete with lingerie , wedding dress and veil, bouquet and of course photographs and it is very popular .
i did go to a gay wedding where one of the partners wore a wedding dress and it was a lovely day .
i do hope your friend has the best day and enjoys her experience .xxx

This is one of my big fantasies, the closest I've come to being a sissy bride is getting engaged although that didn't last. I have indulged my current boyfriend and a couple of exs by wearing bridal lingerie, I took it further recently with my current man by buying very pretty and sexy bridal lingerie from a specialist store and adding a veil before I went to another shop to buy a plain white dress that was close to a wedding dress but not quite there.