Blackmail Sissy Adventure at the Wedding

Blackmail Sissy Adventure at the Wedding

Posted on November 15, 2015

My fiancée Shari and I were staying at a hotel for the wedding of one of her close friends. Shari was in the wedding party so was busy with various things, leaving me alone in the hotel room. I took my swim shorts from my suitcase, intending to go for a swim in the hotel pool. But, as I undressed, another thought occurred to me.

Instead of putting on my swim shorts, I took a pair of Shari's panties from her luggage. She wasn't going to be back for a while, but I wasn't taking any chances, so I bolted the door. I pulled on her panties and looked at my reflection in the mirror on the wall beside the bed. As always when I put on her panties, I imagined being found dressed like that and being forced to kneel on the bed, the panties being pulled down and a hard cock fucking my ass. I watched in the mirror as I masturbated and my cum spurted out over the mirror. 

I cleaned up, put Shari's panties back in her suitcase, put on my swim shorts and went down to the pool.

I dozed off lying on the chaise lounge beside the pool. I woke up hearing someone saying hello. I opened my eyes to see Dan smiling down at me. Dan is the boyfriend of Shari's friend Carol. I don't much like him.

"Sorry to wake you from your sweet dreams," he said, looking at my swim shorts.

I looked down to see that my cock was hard again. I felt myself blushing. I reached for my towel and put it over my cock. I hoped he would walk on, but he spread his towel on the chair next to mine and sat down, still looking at me. 

"That's the drawback of wearing such tiny shorts," he said, still smiling his irritating smile. "Everyone can see what you're thinking about."

"Shari likes them," I said, lamely.

"I can imagine," he said. "They're very cute. Especially when you shave your legs and have such a nice tan."

Before I could help myself I started explaining again. "I run a lot," I said, "and like to have a massage occasionally. And my massage therapist likes it if I shave."

"So you wear skimpy shorts because Shari asks you to and you shave your legs because your massage therapist asks you to? You do like to please."

I said nothing, hoping that was the end of his comments. But no. 

"So how far up do you shave?" he asked.

I should have got up and walked away, but instead, for some reason, answered him. "All the way," I said quietly.

"And did Shari ask you to, or do you get massaged there too?"

"Shari," I said, even more quietly.

"That must look very pretty. Does she ever dress you up? I mean in girl's clothes? You have such a girly figure."

"I have to go," I said. I stood up and walked past him back to the hotel, holding the towel in front of me.

Back in the room, I locked the door, trembling with embarrassment. I looked at myself in the mirror, still holding the towel. I let it drop and saw my cock pressing against my swim shorts and imagined how it must have looked to Dan as I lay on the chaise lounge. Shame flooded through me as I thought about his questions and my answers. Why did I say anything? How could he have guessed that I dress up? 

I pulled my shorts down over my cock and turned to look at my ass in the mirror. Had he watched my ass as I walked past him? Did he think my ass was as girly as the rest of my body? Did he get hard looking at me? Despite my embarrassment, the thought that he might have been turned on made my cock harder, and I started stroking it. I went back to Shari's suitcase and retrieved the panties I had worn earlier. I pulled them on and looked again at my ass in the mirror.

The phone rang. I froze. Maybe it's Shari, I thought, calling to tell me she's on her way back the room. I lifted the phone. It was Dan.

"Hi," he said.

"Hi," I replied.

"I didn't mean to embarrass you earlier," he said.

"That's ok," I replied, wanting to get him off the line quickly.

"Carol just called to say the girls won't be back for another hour or so," he said.

"Ok," I answered.

"So I was thinking that maybe I could come by to see you."

"What, in my room?" 



"I thought you might like company."

I panicked. "No. No thanks," I said. I hung up. I sat in front of the mirror trembling again. He knows, I told myself. He knows my secret.

After a couple of minutes my panic subsided. I focused on my reflection and how feminine I looked. My hand went back to my cock. I thought of Dan standing over me looking down at my cock bulging in my swim shorts. He has a nice body, I thought, and he's good-looking, despite that damn smile. As I stroked my cock, I imagined that he had come across me lying on the chaise lounge dressed in panties, not swim shorts. I imagined that I could see his cock getting hard in his swim shorts. I imagined him taking my hand and leading me back to his hotel room as everyone by the pool stared at me. I imagined him putting me on my knees on the bed, slowly pulling my panties down over my smooth legs . . .

Could I do it? I asked myself. Could I tell him to come down? I'll leave it to chance, I decided. I'll call him back. If he's there, I'll ask him to come down.

I called his room. He answered at once. "Hello. This is Dan."

I took a deep breath. "Hi, it's me," I said quietly. "Would you still like to come by?"

"Yes," he said. "How long do you need?"

"Give me five minutes," I said. I hung up the phone and went to the bathroom and put on some blush and lipstick and eyeliner. I took Shari's very short, very sheer chemise from the bed and put it on and tied the belt around my waist. I turned off all the lights except a small lamp beside the bed and pulled the blinds closed. 

When Dan knocked on the door I opened it just enough to let him in then locked it behind him. He stood in the middle of the room looking at me. "Come closer so I can see you better," he said. I took a few steps towards him. He looked me over, the same smile on his face. "Very pretty," he said. "Are they Shari's panties?"

"Yes," I said, quietly.

"Does she know that you put on her panties and invite men to your bedroom?"

"No," I said. "I've never done this before."

He undid the belt of the chemise and put his hands on my waist and pulled me toward him. He kissed me firmly on the lips and his hands moved down from my waist and slipped inside my panties to hold my ass. He kissed me again, his tongue searching out mine. I stopped resisting and returned his kiss. Then he stepped back and pulled his t-shirt off over his head, and, his eyes fixed on mine, undid his jeans and let them drop to the floor. His cock was hard and very big. I stared at it.

"You like my cock?" he asked.

"It's beautiful," I said.

He sat on the edge of the bed. "Come here," he said. I stepped toward him. ""Kneel between my legs," he said.

I knelt in front of him, his cock level with my face. I took it in my hand, a rush of excitement coursing through my body as my hand closed around it and felt its hardness. I started stroking it. As his moans grew louder his hand went to the back of my head. He pulled my face down toward his cock and I took him in my mouth as I continued to stroke his shaft. He came almost as soon as my tongue touched his cock, spurts of his cum shooting deep into my mouth and spilling out over my lips and chin. 

When his orgasm was spent he lifted my head from his cock. He stood up, pulled on his jeans and t-shirt, and left the room.

I remained on my knees where he had left me, my head resting on the edge of the bed. I turned so I could see myself in the mirror. My lipstick was smeared with his kisses and there were splashes of his cum on my face. Shari's chemise was falling off my shoulders and her panties were pulled down around my thighs. A wave of shame rushed through me. How did I allow him to use me like that? I stood up and took off the chemise and panties. But my cock was still hard. I looked at myself in the mirror, disgusted by my excitement. No, I resolved, I'm not going to touch myself. I'm going to get myself under control.

I put the chemise back on the bed and the panties in Shari's suitcase. I showered, scrubbed her makeup off my face, then brushed my teeth, desperately wanting to get rid of any trace of his semen from my mouth.


That night at the rehearsal dinner we sat at a different table from Dan and Carol. But half-way through the evening he sent me a text. "Our next date: when the girls leave tomorrow for the wedding."

"No," I replied. "Never again."

That night, when we went to back to our room, Shari was talking about what our own wedding would be like. I felt disgusted with myself as I remembered what I had done in that room a few hours earlier. My self-loathing was complete when she walked out of the bathroom wearing the chemise I had been wearing as Dan's cum had spurted into my mouth.


Shari was up early the next morning. I lay in bed watching her get ready for the wedding. When she left, I showered. There was a text from Dan waiting for me when I got out of the shower. "We have an hour," he said. "I'll be down in 10 minutes."

"I told you. No." I replied.

His next message was one word. "Listen." He had attached a sound file. I opened it. The first few seconds were silent. Then I heard his voice. "Come closer so I can see you better," he said. A few more seconds of silence followed, then his voice again: "Very pretty. Are they Shari's panties?" "Yes," I answered. Then his voice again: "Does she know that you put on her panties and invite men to your bedroom?" "No. I've never done this before," I said. I listened to the rest of the recording with my head in my hands. "You like my cock?" "It's beautiful." Then: "Come here. Kneel between my legs."

Dan texted me again. "Did you know that cell phones could make such a good recordings?"

"Please delete it," I wrote back. "I'm begging you."

"We can talk about it," he replied. "When I come down to see you."

"You'll delete it if I let you come down?"

"If you suck my cock as well as you did yesterday."

I had no choice. "Ok," I wrote.

I made myself up and selected some panties from Shari's suitcase. I put them on and put on her chemise again. I remembered the white knee-high stockings she had been wearing the night before. I put them on, then looked at my reflection in the mirror. I was hard already.

I let Dan into the room. When I closed the door behind him, he took off his shirt and jeans and stood in front of me, his cock pointing up towards my face. I stood staring at it, half of me wanting to fall to my knees and have him fuck my mouth, the other half struggling to control my urges. 

He smiled at me. "Turn around so I can see your cute ass."

I did. He stood behind me. His hand went to my face and he twisted it back toward him so he could kiss my mouth. His other hand went around my waist and he pulled my body back against his. As I leaned back onto him, I felt his cock against my ass. I opened my mouth to receive his tongue and relaxed my body, positioning my ass so his erection was between my cheeks. He began to move his hips, slowly rubbing his cock against my ass. I moved with him, feeling his hardness, feeling wetness seeping from the tip of my cock into Shari's panties. 

Then he slowly lowered my panties down over my ass. His hands held my cheeks, spreading them apart, and he ran the tip of his cock between them, up and down, up and down. I leaned forward, steadying myself with my hands on the wall either side of the mirror, opening my legs to spread my ass wider so he could caress it with his cock. I looked at my reflection, seeing my smudged lipstick, my panties pulled down around my thighs, my white stockings, my cock erect under Shari's sheer chemise. 

I looked back at Dan behind me, his face not smiling now but showing his excitement as he rubbed himself again me, with each motion his cock passing over my opening and pressing lightly against it. Each momentary push of his cock started a tremor running through my body causing my cock to pulsate. Then he was pausing longer against my opening, pressing harder. He pushed a little way into me, then withdrew, and then, a second later, pushed again. Please, I was thinking, this time, let me have it all. 

Then, suddenly, he was inside me. We moaned aloud as he penetrated me. His hands held my hips and I braced myself more firmly against the wall as he thrust into me, deeper and deeper still. I watched his face in the mirror as he fucked me, his eyes returning my stare, his mouth open as he moaned his excitement. With each thrust of his cock his balls and thighs pressed against me and I imagined his cum starting to surge deep inside him, soon to spurt out into me, to fill me with his semen. His face relaxed for a moment, then, as his orgasm shuddered through his body, his muscles tensed and his eyes closed and his mouth let out a long loud moan. He pressed his cock deep into me and held it there, his hands on my hips pulling me forcefully back onto him as he shot his cum into me. 

We stood together, my body impaled on his, not moving, our eyes meeting each other's in the mirror. Then he pulled out of me. I turned away from the mirror to face him. My cock lifted up Shari's chemise, my excitement visible through the sheer material. I sat on the edge of the bed to try to hide my erection from his eyes. 

"You'll erase that recording?" I asked him.

"Maybe I should keep it so you can pretend you're allowing me to fuck you because I'm blackmailing you."

"No. Please destroy it!" 

"I will, I will," he said in a bored tone. "Just one more thing though. I'm going to watch you play with that." He pointed to my cock.

"No," I said. "I don't want to. That wasn't the deal."

"That's the deal now."

"I don't want to. I want to stop doing this."

He knelt in front of me and forced my legs apart. His face went to my cock. I tried to push him away but he pushed me back on the bed. He took my cock in his mouth. I can prevent myself cumming, I thought. I tried to imagine Shari walking in and seeing me as Dan had fucked me, her panties down around my thighs. But now I couldn't shame my excitement away and I felt my orgasm start to build as though someone were slowly turning up a dial. My release was almost in slow motion. I reached the point where it couldn't be stopped, but still I felt it build, and for a few seconds I was poised on that precipice, watching in the mirror the look of incredulity on my face as I waited for my cum to explode into his mouth. Then, just when the delay had become unbearable, he took his mouth from my cock, and sat back and looked at me. I knew what he wanted me to do and I couldn't stop myself. I took my cock in my hand and made myself cum, pleasure crashing hard though my body as my cock spurted out long streams of cum.

I lay back on the bed as though in a trance. Some part of me realized that Dan had dressed and left. I stared at my reflection in the mirror. My nipples were hard and I wondered whether I had been pinching them as Dan sucked my cock. Shari's panties were no longer around my thighs and her chemise had fallen off. All I was wearing were her stockings. I looked so wanton, so trampy. My cock glistened with his saliva and my cum. I took it in my hand and squeezed some final drops of cum onto the tip of my finger and put my finger between my legs and gently rubbed my cum around my opening. I shifted my position on the bed and spread my legs wide so I could watch what I was doing in the mirror. I pushed my finger a little way into my opening and slowly fucked myself, trying to recapture the feeling of Dan's cock inside me. I imagined that what I was seeing in the mirror was a video, and as I imagined that, the next scene of the movie rushed into my mind: me on my back and Dan standing between my legs, his hands on my thighs spreading my legs wide, and fucking me as I watched him thrust deep into me again and again and again. 


He texted me that evening as I sat on the bed waiting for Shari to finish in the shower. "Don't you want to know if I've erased the recording?"

"Have you?" I replied.


"Thank you," I wrote.

"You're welcome," he replied. "So when will you dress up for me again?"

"I won't," I replied.

"It looked to me like you had a good time."

"But you're still a jerk," I replied.

"What's that got to do with it?" he wrote. "You've got Shari for nice sex. When nice isn't what you want, let me know."

"Never," I replied, even as my cock began to stir as the image of him standing behind me fucking me up against the mirror rushed through my mind.

Story by: RickeeDavala