Emotional Blackmail

Story Info
A jilted bride exploits a male friend's compassion.
1.5k words
4.29
64.8k
41

Part 1 of the 2 part series

Updated 06/08/2023
Created 09/30/2017
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I am crying when I open my front door to you. Without a word I put my arms around you as you stand on the doorstep and embrace you for a long time.

"Thank you for coming," I say after a while. "I really needed a friend." I release you. "Come in. I'll get us both a drink. I think we need one."

I lead you up the stairs of my flat to the sitting room. This, I tell you as you sit next to me on my sofa, is where I have been hiding since my fiancé called off our wedding.

This comes as news to you. Everyone at the ceremony was given the impression that my would-be husband had missed his flight, but the truth is more complicated.

He missed it on purpose because he couldn't bear to go through with the wedding I had arranged for us.

You listen dutifully as I tell you how it had all been going so well. I cup my face in my hands and compose myself. I take your hand. "You've always been such a good listener," I say. "I will tell you everything."

I had been encouraging my fiancé to wear my clothes, just privately at first. I explained to him how women are objectified when men give them sexy clothes, which he understood straight away, and he could see why I wanted him to know how that felt.

"It started with a pair of knickers," I say. "Nothing fancy. Just some old black satin ones of mine with a bit of lace round the top. I told him I wanted him to wear them during sex."

I stop crying as I recall how easy it had been. I used them to caress his cheeks and nipples, laid them out over his pelvis, gave him a squeeze and he was ready for me to help him put them on.

"I kept him hard in them for about an hour before I made him come. I told him not to clean himself up. He wore them while he went down on me and kept them on all night.

"From then on he always wore my clothes during sex. I think it was a camisole next, or a slip. I would order him the girliest things I could find on eBay and have them sent to his office, so he would have to bring them home.

"If he wore them home I would ravish him the moment he got in," I say, and I smile for a moment. "Although he would only do that with the underwear. The blouses and skirts only went on when he got home, and that could be a struggle until he accepted that wearing them was a condition for anything more than kissing.

"He kicked up a fuss when I ordered him his first dress. I thought I'd gone too far. It was a French maid outfit, all in pink satin with ridiculous frills and bows everywhere and he couldn't handle it. I got really upset too and as he walked out I threw the dress into the street and told him not to come back without it on.

"But you know what he's like: he can't bear confrontation. He rang the doorbell and I found him in tears, holding the dress. We got him dressed and I decided to go all out."

I'm looking into your eyes as I tell you this. You try to look comfortable. I put a reassuring hand on your knee.

"I had been teasing him about his anal virginity for a while, making him take a finger as he came, but I hadn't told him that I wanted to take him properly. The maid's outfit made him totally meek so I told him to get on his hands and knees and close his eyes, and he did it, bottom in the air. When I eased in the strap-on he whimpered and he moaned but there was no fight in him, even when I got carried away. He asked me to stop. He begged me, actually, and he might have tried to use our safe word but I told him that he had to learn what it's really like to be vulnerable.

"I turned him over and took him in my hand and he came like I'd never seen him do before.

"He never resisted me again after that. That was when I started planning our wedding."

My lip starts to quiver as talk about my preparations for the ceremony. I describe how I measured him for a wedding gown and planned every detail of our day, then my face crumples with sorrow. "It was going to be perfect. He was going to look so gorgeous. It was all set up and then, with a few hours to go, he just goes and bottles it."

Tears fall down my cheeks and my voice cracks. "I spent I don't know how much money on that dress and it's just hanging in the bedroom, never to be used."

I collapse into your arms and hold you tightly. Between sobs I tell you how beautiful the dress is. "That's what gets me the most. It's just such a fucking waste. I've wasted everything."

You hope that our hug will help me to regain my composure but it doesn't. You murmur that I haven't wasted everything. I slowly look up at you.

"You mean...?" I say. "Would you? Would you do that for me?"

You look confused. I wipe my tears.

"You don't have to wear it in front of anyone else, I promise," I say, brightening a little. "Here, come and take a look with me."

I take your hand and bring you to the bedroom, where a white satin dress hangs on the door. I usher you in and sit you on the bed. The dress is more discreet than you might have thought. There are no bows and little in the way of lace. It is high-necked, floor-length and fitted at the waist.

As you look at it you feel a soft caress on your cheek and you see that I am holding a pair of white bridal knickers. You can see the tear marks on my cheeks as I lean over to unbutton your shirt.

"Oh, thank you for doing this," I say. "It means the world to me."

I undo your belt and tell you to stand up. "Take it all off now," I say. You falter so I help you. I take your clothes away then hand you the knickers to hold while I fuss about your waist with a suspender belt. You bend down to cover yourself up with the knickers.

"Not yet, silly," I say. "Stockings always go on first."

I kneel as I roll the white, lace-topped stockings all the way up your legs, allowing myself a smile as I watch you twitch each time I fasten the suspenders.

I tell you that you can put on your knickers now and you obey while I ready the dress. It goes over your raised arms and head and drops down smoothly over your body. You hear the zip as the fabric pulls tight.

I squeal with delight and get you to twirl for me. Your face is crimson with embarrassment. While you reach up to fumble with the zip I seize my chance. I bend you over the bed. "Still now," I say. I flip up your skirts and pull down your first pair of knickers. Perhaps you think I am helping you to undress again.

"Be still, my virgin bride."

You feel my finger spreading a cool gel onto you, then into you. You protest weakly but I talk over you. "You need to relax, darling. Deep breaths. In... and out."

I repeat the words "In... and out" softly. You feel a gentle pressure and then a sensation of wetness and stretching as I enter you. A little bit at a time, I pull myself towards you till my thighs touch your bottom. You groan helplessly as the strap-on pins you down.

"Let it happen," I say. "Just let go and give in to what I'm doing to you."

My thrusts are slow at first, building in tempo as you learn to relax your body. Your head lolls. I move faster and harder.

Now it is your turn to cry. "Oh baby," I say, slowing my pace. "Shall we stop? Lie on your back."

I help you to flip over but I don't want to stop. I push your legs apart and guide myself into you again. I lean in deeply and kiss you tenderly, over and over. I tell you between kisses how beautiful you look.

I lean back at last for a final humiliation. I tell you to push yourself onto me while I stroke you to orgasm. "Come on, it'll all be over soon," I say. "We're almost there, aren't we? All the way from best friend to newlywed."

You sigh, then gasp, then groan, then all three together and it's more than you can handle. You buck and writhe, squeak and moan, subside and whimper.

I pull away at last. I draw your knickers back up and smooth down your skirts. We lie together. "You rest, darling," I say softly. "I'm going to take care of everything."

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8 Comments
robert0000robert0000about 4 years agoAuthor
Re: Beautiful

Perhaps if your sexual partner read this you could both recreate it. Come back here afterwards and tell me how it felt.

4yourpleasureiam4yourpleasureiamover 4 years ago
Beautiful

I so love being the girl for my partner. One feels so special and it is so much nicer than having to get all hard and stiff. Besides crying lets out the inner self and frees one from being in charge.

AnonymousAnonymousover 4 years ago
Brilliant story

Excellent love your writing let's have some more. I think this is your best story.

robert0000robert0000about 5 years agoAuthor
Re: So hot

Thank you. The crossdressing is really just a proxy for objectification. Dressed up, the male character feels an expectation that he should be passive. The usual tension between his propriety and sexual desire is skewed because his sense of responsibility is removed. He thinks that the most appropriate thing to do is to entrust the female character with all the decisions.

She, meanwhile, interprets his clothing as a provocation, a licence to release her own sexual desire.

It’s quite sexist, really, because it implies that femininity equals passivity and that sexy clothing is an invitation. My only defence is that this is fantasy, and that in real life I think that anyone should be able to dress how they please without fear of unwanted sexual advances.

MagnificoGiganticusMagnificoGiganticusabout 5 years ago
SO HOT!

I'm not into the whole cross dressing thing, but it doesn't bother me. What I am into is the role reversal, her gentle but urgent and cajoling domination, the overbearing motherly sort. I love his submissive silence, the humiliation of being taken like a girl, and worse, that he isn't stopping her, isn't really resisting, the physical cues that admit that he actually likes it, likes to be submissive, the bottom, which society tells us is so unmanly but turns him on so much. Her dialog about "letting it happen" and just accepting it, is very hot. Wonderful story. I only wish the sex scene was even longer, and had more "verbal teasing" on her part, but what is in there now is so spot on. I love it. Thank you!

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