My GF [21F] Turned Me [21M] Into a Sissy

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It’s been a while since I’ve posted so I figured I’d provide an update on what my girlfriend, Katie, and I, Taylor, have been up to since my last post. For previous posts see my profile.

A few weeks after our weekend with Josh, Katie and I really began to open up to each other sexually. I mean I had watched her fuck other guys that weekend and she had watched me do the same. Our biggest thrill that weekend was watching her get fucked by TJ and Marcus, two black guys that Josh had invited over to turn her into a slut. In the weeks following that weekend, Katie was a sexual fiend. She wanted sex all the time and would talk dirty to me about how much she loved fucking other guys in front of me. I would ask Katie to describe to me how much she loved fucking big black cocks and she would tell me how much superior they were than my little white dick which would usually make me cum instantly. She would also have me cum on her tits, ass, or feet and have me lick my cum off of her.

Also in the weeks that followed that weekend, she had met up with Josh a few times. She’d go over to his place to fuck him and would come to my place afterwards and have me eat her out while I jerked off and licked his cum out of her. Katie really took a liking to Josh and would mention him constantly while we were together which was a turn on while we fooled around but at other times it seemed like she was either trying to make me jealous or was really into him. For example, we went out to a restaurant and she mentioned that Josh would really like this place. It made me jealous that she was thinking of him when sex wasn’t a topic of discussion.

About a month after that weekend with Josh, Katie had come over one Saturday evening and we had the usual boyfriend/girlfriend type of evening. We ordered delivery and watched a movie. However when I tried to touch her, she pulled my hand away multiple times. I finally asked her what was up and she told me that she had been hanging out with Sarah a lot (see previous post) and that they had discussed having another fun weekend. I was intrigued.

I asked Katie what she had planned for this coming weekend but she was vague and said that we would be hanging out with Scott and Sarah next Saturday and we might have a few guests as well. I started kissing Katie’s neck and begged her to tell me more and to my relief she reached over and grabbed my dick.

“You’ve been talking a lot about me fucking other guys and I know it turns you on. I was thinking we could hang out with Sarah and Scott next weekend.” She said.

“Do you want to fuck Scott?” I asked.

“Well, not me” she said. “But perhaps you might be able to fuck Sarah if you’re interested.”

I was absolutely intrigued and asked her to tell me more as she stroked my dick. Katie surprised me by asking me to imagine what Sarah’s pussy felt like and asking me where I’d like to cum. In or on Sarah. I told her that I’d love to fuck Sarah’s ass.

“Yeah babe” she said. “Do you want to pump your cum in Sarah’s ass?”

“Oh fuck!” I moaned. “I want to cum so deep in her ass. Keeps stroking me. I’m about to …”

With that, Katie took her hand off of my dick. “You better not cum. In fact, you’re not going to cum all week. Got it? No jerking off!” I tried to pull her hand back to my dick but she pulled it away and told me she was serious. As I was still rock hard, I grabbed my dick but before I could start jerking off katie slapped my balls. “Fuck!” I moaned. “I told you, no cumming until next weekend. I promise you babe, it’s going to be worth it when you finally shoot your load!” She said.

As we went to bed, I asked Katie one more time to tell me the surprise but she refused. After insisting a little she finally gave in and said that she had booked me an appointment on Thursday afternoon and that she would be over Friday. With that she told me to stop talking, gave me a kiss on the forehead, and told me to go to sleep.

The next morning I woke up alone.there was a note on the pillow that read “Taylor, I love you and am so excited for next weekend. Remember, no cumming!!!” I grabbed my dick immediately and started stroking it thinking about Sarah but right as I was about to cum I pulled my hand away. It was agonizing but I took a cold shower and made breakfast.

Monday I woke up with a boner and began stroking it thinking about a threesome with Katie and Sarah. Much like the day before, I was able to stop myself right before cumming. “Fuck!” I thought, “hold out for Saturday and I’ll get to fuck Sarah.”

On Tuesday I woke up with another boner thinking about Katie sucking Scott’s 7” cock. I stroked myself thinking about my beautiful red headed girlfriend sucking a nice big cock. Once again I stopped myself right before.

On Wednesday, I woke up to a dream of Scott’s cock fucking Katie. I remember stroking myself while still half asleep and thinking about his dick in her pussy while I licked her clit. I was about to cum before realizing what was doing and got up to take my mind elsewhere.

Thursday was the day of my appointment and I woke up with the thought of Scott’s big cock in my mouth. I stroked myself to near completion imagining he was cumming in my mouth. I was so tempted to cum but I happened to look at the clock and realized i had the appointment that Katie had booked for me in an hour. I quickly got ready for the day and headed to the address she texted me earlier in the day.

I arrived to my appointment at a salon not sure what services Katie had booked for me. Once the technician called me back, she told me to fully undress and lie on the table. “Do I need to take off my underwear?” I asked. “It’ll be kind of tough to complete the full body wax with your underwear on.” She replied. The next hour was awkward and slightly erotic as a cute Asian girl explored my body while waxing my body hair off. I left the appointment as hairless as I’ve ever been.

Friday arrived and I was so excited that Katie was coming over later that I didn’t even think about stroking myself. I got up and spent the day doing homework, cleaning, and grocery shopping. Katie arrived around 7pm and I was so excited to see her that I started making out with her and dragging her to the couch once she arrived at my apartment. Katie told me that I still had one more day but to undress so she could see how hairless I was. I mean i’m not a hairy person to begin with but being absolutely smooth around my dick, balls, and ass was a weird feeling. I thought this is what women go through for their guys. I then got dressed and we watched a movie before going to bed.

Saturday had finally arrived and I woke up excited and started kissing Katie’s neck and rubbing her nipples as I pressed my hard dick against her toned ass. She was still out of it but quickly came to and told me I had to wait until the evening and to go get ready for the day. After I finished getting ready, it was about 9 and Katie then went to get ready while I scrolled on my phone for a bit. She finally came out of the bathroom looking as beautiful as ever. I was admiring her pale freckles skin, perky tits and tight body. She was wearing a tiny tshirt and short jean shorts that showed off her amazing legs and ass.

“Are you ready?” She asked. “For what? I’ve been wondering this all week!” I responded. Before she could answer there was a knock at the door. I had a confused look on my face but Katie jumped up and said “Noah’s here!” I didn’t know who Noah was but Katie went and answered the door and came back into the room followed by a good looking guy. He stood in the living room and looked at me so I stood up to shake his hand but Katie swatted my hand away. “Get on your knees Taylor!” She commanded. I obeyed and got on my knees if front of them and looked up at them as she kissed his cheek and asked if he was ready for his blowjob. He said yes and started to undo his pants but Katie told him that I could do it.

“Taylor, you know what to do right?” She asked. I nodded and reached towards his pants and started undoing them. I grabbed the top of his boxers and started pulling his pants and underwear down together revealing a long thick dick inches from my face. I grabbed a hold of it and started stroking him, feeling it grow in my hand. “Go on. Suck it.” Katie commanded. I leaned forward and took Noah’s hard dick in my mouth. “Oh fuck, that feels amazing” he said “I don’t think i’m going to last since you made me wait a whole week!” With that being said, I knew he was going to have a lot of cum. I sucked him for another few minutes and before long he said he was cumming. I felt it shoot into my mouth and he quickly filled my mouth with his cum as I stroked it all out. When he was done Katie told me to show them my reward and I carefully opened my mouth, careful to not spill any. “Swallow” she said and I gulped down his warm cum and gave his dick one final suck before he pulled his pants up, thanked us, and left.

“You’re such a good cocksucker” she said. “Is it my turn?” I responded. “Not yet babe” she said as she had me get up and give her a kiss. “It’s only 10:20 and I have another surprise for you in 25 minutes.” “Is it another cock to suck?” I asked. “Of course babe” she said as she gave me a kiss.

At 10:45 exactly there was another knock at the door. Katie brought in another good looking guy who seemed a little nervous but that quickly faded as she got on her knees next to me and pulled his cock out. “I’m going to suck this with you” she told me as she quickly took his cock in her mouth. After a minute her so, she guided my head towards his hard dick that was slick with her spit. I eagerly took him in my mouth and started stroking him while I sucked his big hard dick. Katie sat back and watched as this second guy, whose name I didn’t know, started erupting in my mouth. I swallowed as much as I could but it didn’t stop shooting out of his cock and so much landed on my face before I put it back in my mouth and swallowed the rest. Katie then scooped what was on my face and had me lick her fingers clean and he pulled his pants up and headed out. I got up to pee and get a drink of water and when I came back to the living room, I heard a knock on the door. I looked at the clock and saw it was exactly 11:30.

I won’t bore you all with the details but this went on for a few more hours. 8 cocks later and the last guy left around 03:45. I was looking at the clock but Katie told me that no one else was showing up and to take my dick out because it was my turn. “Yes!” I thought as I pulled my rock hard dick out of my pants. I was leaking precum like crazy and felt like I would explode at any second. The second my dick felt her mouth I knew I was about to cum and I told her so. The first shot filled her mouth, which she clearly wasn’t ready for because she started coughing. I grabbed my dick and stroked out the rest of my cum watching as it sprayed her face. I was like a one man bukakke as I coated her beautiful face, lips, and mouth with a weeks worth of my cum.

Katie laughed and called me a good boy as she got up. “I’m going to get ready, we’re leaving soon for Sarah’s.” I sat down on the couch with my dick still hard. I felt like I could cum a few more times easily so I was looking forward to what the girls had planned for tonight.

After a bit, Katie came out looking absolutely sexy. She was wearing a short skirt, tank top, thigh high socks and boots, and had her makeup done perfectly. I got up to give her a kiss but she guided me towards the bathroom. “Go get ready! Also there something on the counter. Use it. I want you nice and clean!” As I got into the bathroom I noticed an enema kit. I think I had an idea for where the night was headed so I used that and took my shower after coming out into the bedroom in just a towel. Katie then had me drop the towel. “I’ve got to get you ready for tonight” she said as she started putting lotion all over my body. Not just any lotion but girly smelling lotion. I asked her why she was putting that on me and she explained that she was going to get me dolled up. After she was done with the lotion, Katie pulled out a small butt plug and started applying a little bit of lube to it. “Bend over” she instructed me. I complied and felt the cool metal against my ass as she put it in. “Now get dressed” she said as she pointed to an outfit on the bed “you’re one of the girls tonight.”

It was an outfit similar to hers. Skirt, top, thigh high socks, panties that went up my ass. After I was dressed, Katie had me sit down and started applying makeup to me. “Wtf is going on” I thought but at the same time I already knew. Finally, she put a wig on me and sprayed me with perfume. “You look sexy babe! Check yourself out in the mirror!” As I looked at myself, I thought I was barely recognizable. I looked like a girl. I don’t really have a masculine frame to begin with and even I wanted to fuck me. “Let’s go, we’re going to be late!” She said as she pulled me out the door.

We got to Scott and Sarah’s about fifteen minutes later and Sarah shouted “damn you girls look hot! Don’t they babe?” Scott agreed and leaned into give Katie a hug as she kissed his cheek. I followed her lead and went to give him a hug and kiss on the cheek but he pulled me in tight. I could feel his dick pressed against me as he grabbed my ass and whispered in my ear “we’re going to have some fun tonight”. Sarah laughed and said that he’d been looking forward to this all week. “Come in for a drink before the guys get here.” Sarah said.

We grabbed a drink and went to the living room to chat. I went to sit next to Scott but he insisted that I sit on his lap. As we talked I could feel his cock pressed against my ass as he caressed my hips and played with my panties. Before long we heard voices outside and the doorbell ring. “Taylor, can you get the door?” Sarah asked. As I got, I felt Scott squeeze my ass and I smiled. Once at the door I opened it to find Josh and Logan. I started to step aside as they introduced themselves to me and stepped inside. Once I told them I was Taylor, they all looked shocked. “Holy shit, you look hot!” Logan said as he pulled me in for a hug. I could feel his long dick against my leg as I hugged him and I immediately felt my dick twitch at the thought of him.

As we walked back into the living room, everyone grabbed a drink and got comfortable. I sat down next to Scott, who immediately put his hand on my thigh, and Logan sat down on the other side of me and did the same to my other thigh. Josh had grabbed a seat right next to Katie. We all hung out drinking for a bit before there was another knock at the door. “Omg they’re here!” Sarah said as she shot up to answer the door. She went to let TJ and Marcus in and quickly offered them a drink before sitting on TJ’s lap.

As we all sat there drinking, Sarah became more and more comfortable and eventually started making out with TJ. Scott still had his hand on my thigh and started moving his hand up towards my panties before grabbing the back of my head and pulling me in for a kiss. As I made out with him, Logan was on the other side of me and kissing my neck while pulling my hand down towards his crotch. I swear it felt so hot to be desired so much that I wasn’t even thinking about what was about to happen next.

With all this happening, Marcus got bold and pulled his cock out in front of Katie and grabbed her hand and placed it around his massive big black cock. I glanced over and saw Katie stroking him but what happened next kind of took me by surprise. “Can I suck him babe?” Katie asked. I broke my kiss with Scott and was about to answer her but when I looked over I noticed she wasn’t looking at me. She was looking at Josh for approval. “Go ahead, but that pussy is mine tonight.” He replied back. I watched as she took his BBC in her mouth and sucked and stroked him but before I knew it Scott and Logan both had their cocks out and had placed my hands on them. I quickly got on my knees and started jerking off their cocks and began sucking them while I kept glancing over at Katie who had her throat filled with a big black cock.

Before long, Marcus ended up cumming in Katie’s mouth and I was lucky enough to see her mouth filled with his cum before she swallowed. At this point Sarah was riding TJ who was fucking her pussy with every gigantic inch of his cock. This is the point that both Scott and Logan were furiously stroking their cocks and telling me to open my mouth. As I stuck my tongue out I could feel a warm load of cum hit my tongue and fill my mouth as both Scott and Logan filled my mouth with their hot jizz. TJ then began to cum inside Sarah’s pussy as she was moaning like crazy. As Scott pulled his dick out of my mouth, I continued to suck Logan’s dick as I watched Scott approach Sarah and begin to eat her out with TJ’s cum flowing out of her pussy.

Josh then got up and sat down next to Katie and pulled his huge white cock out and she instinctively went down and began blowing him. Marcus, still rock hard, brought his dick over to Sarah’s mouth while TJ grabbed Scott from Sarah’s pussy to suck him. I watched as Scott and Sarah sucked TJ and Marcus while I brought Logan’s huge cock back to life with my mouth. Before long, Logan picked me up and turned me around and pulled my panties down. He chuckled as he spotted the butt plug in my ass before pulling it out gently and sliding his cock deep in my ass. As I felt inch after inch enter me, I looked over and noticed TJ and Marcus had bent Scott and Sarah over and they were fucking their asses as well. All three of us were getting our assholes pounded by big cocks while Katie continued to suck Josh’s fat cock. Soon enough, Logan came again deep in my ass while Marcus and TJ both came in Sarah and Scott’s asses before getting dressed and leaving. Josh ended up cumming in Katie’s mouth with her swallowing his huge load of cum.

As TJ and Marcus got dressed and ready to leave, Scott began licking the cum leaking out of Sarah’s asshole. Katie then exclaimed “how am I the only one who hasn’t been fucked yet!” With that, Josh picked her up and carried her to the guest bedroom and shut the door behind them leaving just Sarah, Scott, Logan and Me in the living room. We all got cleaned up and sat in the living room waiting for Josh and Katie to be done but when we finally heard them finish the door never opened. Josh and Katie stayed in the room until what seemed like forever. With that, Sarah said she was going to go to bed and glanced between Scott and Logan. “Logan, do you want to come keep me company?” She asked. As Scott and I listened to Logan and Sarah begin to have sex in their bedroom, Scott pulled his cock out again and told me to begin sucking. I was absolutely exhausted at this point and just wished he would come quick but he did not. I sucked his big cock for probably five minutes before he flipped me over on my stomach and entered my ass. He must have fucked me for probably 20 minutes before cumming in me, cleaning up and falling asleep on the couch.

I laid there, dick swollen and aching to cum as I jerked off thinking about the days events. I had wanted to fuck Sarah but the opportunity never presented itself. I came quick and then washed up, drank some water and fell asleep on the floor next to the couch that Scott was sleeping on.

The next morning I woke up horny as hell. I jerked off in the shower and got dressed. Luckily I had brought normal clothes and looked like my old self again. Once I was done getting ready, I came out and Sarah had made everyone breakfast. I ate quickly and once I was finished I asked Katie if she was ready to go. “I’m actually going to hang out with Josh today. Why don’t you head home and I’ll see you later ok?” She said.

I grabbed my stuff and headed to my car. Feeling rejected and used, I just wanted to go home and go to bed but I couldn’t bring myself to drive away and just sat there with the engine running. After about five minutes, Sarah came by and knocked on the passenger window before getting in. “We can see you sitting here from the window. Katie suggested I come down and talk to you.” She said. In the end I confided to her that I really had wanted to sleep with her that night and she seemed sympathetic. She ended up giving me a handjob before getting out of the car and going back upstairs.

I drove home, took another shower and ate before jerking off and going to bed for a good 12 hours. It’s been quite a few months since this happened but I’ll do my best to provide some updates on events going forward.


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