Sub Crossdresser

Story Info
Girlfriend seizes my Sub Sissy nature.
1.5k words
4.48
25.4k
14

Part 1 of the 2 part series

Updated 06/10/2023
Created 07/14/2021
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sissy171
sissy171
536 Followers

I am bound spread-eagle, standing between two trees.

My girlfriend, Annie, knows I cannot resist bondage; she's been tying me to our bed from our first week together.

Annie has shared openly about my fetish with her best friend Amy. Early in our relationship, she gave me an option, she wanted to discuss my kinky tastes with Amy, or we break up.

I caved. I wanted, no, NEEDED, to be a submissive, crossdressing, slave. Annie enjoyed my kinks. I wanted a partner in life, and I knew how lucky I was to have a partner who embraced my tastes.

We were camping on a local lake.

I knew this weekend would be some sort of "crossing" for me.

Amy and her hubby Dave owned a boat, and they'd been inviting us for months. Annie finally accepted the invitation.

Annie was considerate of my trepidations, but each passing day, she realized our dynamic. I relinquished my power more and more; from 50/50 to 60/40 and working toward 100/0. There was an obvious up-side to being submissive, (unbridled, compounding, ecstasy), but being publicly revealed was a really scary downside. Nonetheless, Annie had made her decision.

Dave had already noticed my shaved legs; I saw him checking them out at a restaurant one night. I didn't know what Amy had told him, but we were about to take a big step.

Dave took the boat back to the dock to get more stuff from the car, so it was Annie, Amy and me. All Annie had to do was give me a look, and I knew it was on. With Amy standing right next to her, she said, "Drop your shorts and shirt."

Amy made a slight smile as I dropped my shorts, revealing my panties. I stood before them, hands behind my neck, legs spread, wearing tiny thong panties, and my cock was growing.

Early in our relationship, I started wearing panties in lieu of boxers.

Annie and I had enjoyed many sexy shopping trips for panties.

All my panties were selected to contain my junk, and my hardon.

I loved wearing panties all the time; it was a constant reminder.

Having my body shaved was another reminder.

Most mornings we fucked before work, but not this morning, so I was already horny, and this moment was supercharged sexuality. My cock grew hard and fast.

Annie reached in her bag and out came four ropes, (they had been fashioned by me months ago). One end had old scarves with ready-made slip knots, that could quickly secure my wrists and ankles. "Set it up," was all she said, and I found myself tying the ropes to the trees.

Two ropes at head height, and two for my ankles. I'd rehearsed hundreds of bondage scenarios in my mind, I knew exactly how much slack to allow. Naked except for thong panties, the girls watched as I set the ropes for my own demise.

The irony was not lost.

"You see," Annie said, "He knows he's about to be exposed, and still he can't resist. He thinks he's a slave to me, but truth is, he's a slave to his own sexuality. I'm just the steam regulator."

She was 100% correct; I trusted my fate to her judgement.

The job was done; the ropes were ready.

"Do your ankles," she ordered, and I put my ankles into the slip-knot loops, and drew them tight. My legs were spread, but not so wide that I was uncomfortable; I could stand that way for a while.

I couldn't reach to loop my wrists, and Annie looped one, and the looked to Amy, "Would you like to do the honors?" Amy took the final rope, and slid the loop over my wrist, and I waited. She did not draw it up, but made me do it. I pulled my wrist toward me and the slip-knot tightened, and that was it, I was inescapably bound.

I closed my eyes and exhaled. Then I felt a hand stroking my cock thru my panties, then down to my balls, tickling my balls thru my panties. I tilted my my head back and said, "Oh God!"

Then I heard the boat coming around the bend, approaching our camp site. Dave was smiling as he approached. Annie was teasing my cock, and Dave was about to see me in this compromised state. I'd known it was coming, but reality overwhelmed.

I heard Annie's voice, "On your knees," and I simply obeyed. The ropes were such that I could barely do it, but there I was, on my knees, between two trees, with my wrists and ankles bound. Annie dropped to her knees, sitting on her haunches, still teasing my cock and balls.

Dave approached, dropping his pants, "Lets get on with this." Clearly they all were in on the plan.

Amy approached with some baby oil, "Open wide!"

I opened my mouth and she squirted baby oil into my mouth, and Dave's semi hard cock approached. The baby oil leaked out the sides as his cock grew hard in my mouth. It was my first blow job, (although Annie had made me practice on dildos). I felt his hand on my head; he tilted my head back so our eyes met as I sucked his cock. He fucked my baby oiled mouth. Both hands were on my head and his cock was going deeper and deeper! I started to gag, and I heard Annie's voice, "Easy baby, you were trained for this."

I returned my attention to his cock, (and noticed Amy was filming everything), and started to resume, but Annie had caught his attention.

In a single swift action, he snatched her up, grabbed her bikini bottom and pulled it down. Apparently he'd gone off script.

Annie stood shocked, her hands instinctively tried to cover her pussy. Then he reached for her top, and she submissively raised her arms, and she was naked. She realized what was happening, and succumbed.

He laid her gently on the ground, and she spread her legs. His cock entered and she let out a long "AHHHHHHH!" (She'd missed her morning sex as well).

Each thrust, she went, "Ahh, Ahh, Ahh, Ahh, Ahh," as he fucked her.

Then Amy was upon her face, lowering her pussy to Annie's mouth.

She was being taken by her best friend, things would never be the same.

Amy said to Annie, "Who am I?"

Annie looked confused. Amy said again, "Who am I?"

Annie stared, and Amy said, "I am your Mistress! Say it!"

Annie whispered, "You are my Mistress. I am your slave!"

Amy said, "And Dave?"

"He is my Master. Fuck me Master!" At which time, he grunted, filling her pussy with his cum.

The only sound was Annie slurping on Amy's pussy.

Amy rose off Annie's face, but Dave was still on top of her, slightly pumping the last bits of his cum into the pussy of his new sex toy.

Amy untied my wrists, and had me lay back. She straddled my waist, pulled my panties aside, and eased my cock into her pussy. It was divine!

She looked down on me, "Who are you?"

I answered, "I am your cock sucking sissy slave."

"Very good," she said. "Are you prepared to spend this entire weekend in girl clothes?"

"Yes Mistress," my cock relishing her pussy, I'm struggling not to cum.

"And wear makeup?"

"Yes Mistress! May I cum Mistress!"

She closed her eyes. I caressed her breasts and began pinching her nipples, and I tried desperately to hold on until she came. She gasped, and started cuming! I felt her pussy twitching, and her moisture ejecting, and I exploded!

She did all the work, I laid still as my cock blew load after load into her pussy.

Annie's orgasms were not so "wet". It was erotic and sexy, to feel Amy's juices flow over my pelvis.

The four of us remained silent for a while, then without a word, Amy climbed upon my face, and I began to lick her clean. "Gently," she said, and I complied.

When she was done, Annie approached, and I licked Dave's cum from her pussy.

Finally Dave approached, and I licked his cock clean.

My ankles were untied, and we all frolicked in the water, Annie and I answering, "Yes Master, Yes Mistress," reveling in our new mutual slave status.

For the rest of the weekend, they remained naked, while I wore a bikini, and by the end of the weekend, I had a deep bra tan.

Dave fucked Annie like she was a new toy, and I licked her clean every time.

Amy had me massage her, and fuck her, and suck her nipples, hard, and for long periods, (until they were actually sore, and my jaws were sore). I gently massaged petroleum jelly onto her nipples at night, and still, she was too sore to wear her bikini bra in the morning.

Annie told Dave she wants to see him to fuck my boy-pussy, so we'll be embarking on a new "training" regimen. They all want to make me more feminized, and I feigned resistance, but I actually can't wait.

The up side of being a slave.

sissy171
sissy171
536 Followers
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9 Comments
cdCindy1cdCindy15 months ago

I can't wait until you tell us about Dave fucking sissy's pussy. That's what I want -- every day.

AnonymousAnonymousover 2 years ago

Very sexy fetish kink love it

AnonymousAnonymousover 2 years ago

Okay get his cock into his boy p**** will continue Dave's cock with dressing woman calls all the time more please

cdCindy1cdCindy1over 2 years ago

Fantastic story. I would love if this happened to me with my wife and our friends. I love sucking cock and I can't wait until Dave fucks your sissy man-pussy,

Please continue with the next chapters.

Hugs & kisses,

cdCindy

AnonymousAnonymousover 2 years ago
Wow

Somehow the Taliban victory doesn't seem so bad now.

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