Exploring My Fetish

Note: This story plays off of my previous 2, taking place after both of them. You won't miss too much but you can get more of the backstory by reading my other 2 stories first.

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I developed to rather uncommon fetish's in pretty uncommon ways through out my life. My first was a fetish around salon capes and haircuts in general. When I was younger I dreaded going to get my haircut because I hated the capes. In early adulthood meshing changed and I suddenly loved being under the cape while a woman cut my hair and loved seeing women under the cape having their hair cut.

My second fetish slowly evolved over the years and the best way to describe it was roll playing what I thought it was like to be a woman. Dressing up in underwear, bras, and other female clothing, giving blowjobs to dildos, and thinking of a woman with a strap-on changing roles with me for an evening of fun. This fantasy really took off when I found an online site and started following some sissy blogs. Much of it was too far for me, but I loved the dress-up and mild sissy captions and shemale posts.

My girlfriend was aware of these fetishes and fantasies but so far hadn't acted on any of them really. She wanted to try anal and some both used dildo's on each other but she had never worn a strap-on.

After Ashley and I had quite the time with her hair stylist Brittany at her salon, Ashley decided to really go all out for me for our anniversary. I came home from work to find both Ashley and Brittany at our house.

"Hi ladies," I said when opened the door.

"Hi sweetheart," replied Ashley. "I hope you don't mind Brittany is here even though it's our anniversary."

"Of course not," I said with a smile. I really didn't mind as Ashley and I had already decided to have dinner and movie night at home rather than going out. Ashley followed me upstairs as I went to change.

"I have a surprise for you babe," she said.

"Oh yeah, what's that?" I replied.

"We'll..." she began. "I wanted to do something really special for our anniversary, and I remember you telling me about your fantasies before so I thought we could just have some fun with that."

"Really?" I said, sort of surprised.

"Of course!" she said, running to the closet. "I'll go get some clothes. Brittany is already waiting downstairs to make you look beautiful."

My hear began to race. I couldn't quite believe that this was happening. Surely she was just joking and was going to pull out a gag gift or something. A few moments later Ashley returned and she had a full outfit for me to wear.

"Here, put these on," she said, sitting them on the bed. Ashley had picked out a pair of pink lace panties and their matching bra, a skirt, and a tight shirt. I started with the panties and slid them up, being sure to tuck in my cock. Next I put on the bra.

"I'll help you with that sweetie," Ashley said, adjusting the straps and fastening it behind my back. Ashley then handed me some socks to stuff in there. "These should give you some nice DD's," she said.

I put the socks the socks in the bra and let Ashley adjust them. Once satisfied, I put on the skirt and shirt she had picked out.

"Let's go downstairs and show Brittany!" Ashley said, obviously excited. "She's going to absolutely love doing your hair."

Ashley grabbed me by the arm and lead me down the steps and into the kitchen. There I saw Brittany standing next to a salon chair.

"The salon was getting rid of their old chairs and let me keep one," Brittany said, giving it a spin. I couldn't believe they both had gone this far for my fantasies.

I stood there staring and smiling for what seemed like hours. Ashley finally snapped me out of my daydream.

"One more surprise babe," she said, fumbling around in her bag. "Turn around."

I around and waited. Ashley took one arm and pulled it behind my back. The next thing I felt was cold metal going around my wrist and a multiple clicks as she fastened a handcuff to my wrist. She grabbed my other wrist and cuffed it behind my back as well, then spun me around.

"Brittany honey, he's all yours," Ashley said, grabbing my arm and leading me towards the salon chair.

Ashley turned me around and sat me in Brittany's chair. Brittany shook out a shampoo cape and threw it over my shoulders and fastened the velcro behind my neck. She reclined the chair into the sink as she prepared to wash my hair. I closed my eyes and let Brittany do her thing. She's given me amazing scalp massages in the past, and this time was no different.

Brittany finished the massage and turned the water off. She wrapped a towel around my head and leaned me upright. She quickly dried my hair and then tossed the towel on the counter.

"Babe," Ashley said. "I think you should thank Brittany for the great job she did."

"Thank you Brittany," I replied.

"No, no, no, that's not what I meant," replied Ashley, walking over to us.

Ashley rubbed her hand against Brittany's crotch and slowly unzipped her pants. She pulled Brittany's cock out and gave it a few strokes to get it nice and hard. Ashley dropped to her knees and started sucking Brittany off. She stood back up and began kissing me. Ashley grabbed my arm and helped me from the chair, positioning me right in front of Brittany. Ashley pulled her lips from mine andI slowly got on my knees. Ashley held Brittany's cock to my mouth and I opened my lips. Brittany pushed in nice and slow, being nice not to choke me.

"Make her cum baby," Ashley said. "You're not done until you've got a mouthful of cum."

I did my best to pleasure Brittany as I had before. I'm sure I was terrible at it as I had no idea what I really needed to do. I tried getting my tongue in there but had no idea if it was working or not. I bobbed my head as fast as I could taking Brittany as deep as I could until she started moaning. I slowed down and focused on the top half of her cock and expecting cum at any moment.

"I'm so close to cumming honey," she said. "Oh fuck I'm going to cum so hard."

"Fill his mouth and cover his face with cum Brittany," encouraged Ashley.

Brittany yanked her cock from my mouth as she got close to orgasm. I closed my eyes and kept my mouth opened, waiting for the cum. Brittany wasn't lying, she came hard as ever. Her first blast hit me on the cheek, then she got a few smaller blasts in my mouth, and finally one on my chin. I swallowed what was in my mouth and opened my eyes. Brittany's cock was still right there with some cum left on it, so like a gentleman I cleaned it off. The cum on my chin and cheek ran down and onto the cape I was still wearing.

The girls giggled to each other but didn't say a word. Ashley grabbed my arm and pulled me back up and sat me back in the chair.

"We're going to need a new cape," Brittany said, pulling this one from my body and fetching a new one.

"Oh my," said Ashley. "It looks like someone is really enjoying himself."

I had a raging hard on by now that the panties was barely holding in place. My precum had thoroughly soaked them in the front. Brittany returned with a large, clean cape for my haircut. She gave it a shake and then draped it around my body. She pulled it nice and tight around my neck and then snapped it closed.

Brittany snapped the #3 on her clippers and began cutting my hair. It wasn't long before she had finished and trimmed up my neck and around my ears. Slugged in a blowdryer and blew all the hair off the cape and onto the floor.

"You look beautiful sweetie," she said. Ashley nodded in approval.

"Since you don't have any money, you'll have to please Brittany again as payment for your haircut," Ashley said, reaching again for my arm. She pulled me from the chair and turned me around. She leaned me over the chair, flipped my skirt up, and pulled my panties down. She then lubed me asshole for Brittany. Brittany carefully and slowly pushed the head of her cock into my rectum.

Ashley then unbuttoned her own pants and slid them off, revealing just a tiny black thong. She climbed up in the chair, kneeling down, and turned her back to us. She reached back and slid her thong to the side, showing of her perfectly smooth pussy and asshole.

Brittany slid in deeper into my asshole.

"Lick my ass babe," Ashley moaned.

I started lightly licking her ass as Brittany grabbed my handcuffs and bottomed her cock out in my ass. I had never felt so full before. My cock was dripping precum through the panties at this point and I thought I might cum right then and there.

Ashley spread her ass cheeks as I kept licking and sticking my tongue in her hole. "Make out with my asshole," she moaned.

Brittany pled her cock back and almost completely out of my ass before thrusting back in. I let out a moan as I put my lips to Ashley's beautiful ass and began making out with her perfectly tight asshole. "Oh yeah baby," she moaned in pleasure.

Brittany let go of the handcuffs and firmed grabbed my hips. I knew she was about to fuck me as hard as possible and really stuff her cock up my asshole. I was right. Brittany sped up her thrusts and made sure to bottom out each time.

I continued to make out with Ashley's asshole as we both let out numerous moans. I tried to shove my tongue as deep in Ashley as I could but it was hard as Brittany pushed and pulled me with such force. I couldn't brace myself very well with panties around my ankles and my hands behind my back.

Ashley pulled her cheeks further apart. "Stick it in as deep as you can babe," she said. I jammed my tongue into her ass as far as I could get it. Ashley began rocking back and forth simulating me tongue fucking her. She synced up her rocks with Brittany's thrusts and I was just along for the ride. I certainly didn't mind.

"I'm going to cum in his ass," Brittany panted.

"Do it Brit, make it drip from his gaping rectum!" Ashley screamed

My tongue was still buried in Ashley asshole, as if I was going to tell Brittany no anyway. Brittany pulled her cock about half way out and I felt her cock swell up. The next feeling I had was that of warmth in my ass as her cum flooded my bowels. I nearly came right there. I put my lips tightly on Ashley's as and continued making out with her asshole.

Brittany slowly pulled her limp cock from my ass. Ashley jumped off the chair and went around behind me to look.

"Oh babe," she said. "Brittany really filled you up!" Ashley began to let some of the cum drip from my ass and into her mouth as she swallowed it up. She gave a quick lick inside my still gaping ass and got most of the cum out before standing back up. I had never had a girl eat a cream pie from my ass before and it sure was hot.

The girls looked at each other and Brittany gave Ashley a nod. Ashley took the handcuffs off of me.

"Ok babe, you've been a good boy. Sit back in the chair," Ashley said.

With the panties still around my ankles, I waddled the few steps to the chair and then sat down. The cape settled over my cock which was standing straight up by now. The girls giggled again.

Brittany positioned herself between my legs and lifted the cape up. She then turned around and slid her pants off. Ashley came up to her and the girls began making out. Brittany reached back and put some lube on my cock before slowly sitting on it. She lowered herself until I had bottomed out in her ass.

Brittany slowly stood up before lowering herself again, and again, and again. Each time she sped up how quickly she lowered herself. My cock was penetrating her rectum as deep as it could go with each bounce.

"Ashley, spin the chair a little," Brittany said with my cock stuffed inside of her.

Ashley spun the chair 90 degrees.

"Now lean it back," replied Brittany.

Ashley leaned it back now as well.

Brittany leaned back on my chest, picked her feet up to the bottom cushion, and put her arms on the arm rest. From her she began riding my cock like nothing I've ever seen before.

We continued fucking as I got closer and closer to orgasm. I never wanted this to stop. Suddenly Ashley got in front of Brittany and spread her ass.

"Put your dick in me Brit," she ordered.

Brittany and I stood up so we could get Ashley involved. Brittany carefully pushed inside Ashley. Once Ashley was comfortable, I re-entered Brittany's rectum. I slid right back in and we resumed our intense fucking. Brittany grabbed Ashley's hips and I grabbed Brittany's. We synched our thrusts up so we were fucking as one.

"I'm going to cum," I moaned to the girls.

"Me...me too," moaned Brittany. "Ashley's asshole...is so tight."

Suddenly Brittany stopped thrusting and unloaded her cum in Ashley's ass. This sent me over the top and I unloaded my cum inside Brittany. I came harder thawed ever cum in my life and Brittany's bowels took it all. I pulled my cock from Brittany's ass and she pulled hers from Ashley's. Now the 3 of us had nice gaping assholes that had all been cum filled.

"Lie down on the floor," Ashley said, turning to me. "I want you to eat this cum from my asshole."

I did as she asked. She then threw her leg over my head and we got into a 69 position. Ashley put my cock in her mouth and I started licking her asshole. Her pussy was soaking wet and dripping onto the cape.

I had licked all the cum from Ashley's asshole as she continued working on my cock. She tasted so damn good though so I just continued on. It must have felt good because she was letting out moans.

"Baby," she moaned. "I want you to bend me over that chair and fuck me like you've never fucked me before. I want you to destroy my rectum so bad I can't walk for a week."

Ashley then stood up and headed for the chair. I stood up and followed. She bent over the chair and I lined up my cock with her still gaping asshole. I slammed my cock all the way in until my balls slapped her pussy. Ashley let out a moan. I continued ramming my cock in her asshole as hard and fast as I could.

"Oh my God baby, yes, YES! Fuck me so hard. Fill me with your cum," Ashley moaned.

I put my cock as deep in her ass as I could and blew another massive load of cum. This one as just as big if not bigger than the load I blew inside Brittany. I kept my cock in Ashley as we both took time to catch our breath. Finally my limp cock fell out and we both stood up.

Ashley and I had been so consumed with our session that we totally forgot about Brittany. It turns out she had been jacking off while I ravaged Ashley's asshole and was about to cum again.

Brittany came up and forced me back into the salon chair. She climbed up on the foot rest and continued jacking off. Finally she came again and came all over the front of the cape. Brittany climbed back down from the chair. Both of the girls began getting dressed as I continuo sit there and take in what just happened.

Once dressed, Brittany came behind the chair and unsnapped the cape. I stood up and Ashley handed me my normal clothes. As I got changed the girls cleaned up and Brittany headed home.

"Was that everything you hoped it would be?" Ashley asked me.

"And more," I nodded.

"Good, because tomorrow you get to indulge all of MY fantasies," she responded with a smirk.