I started dating a girl and I was scared she wouldn’t understand my kink.
I met Jenny not long after my 19th birthday. She worked at a music shop and I’d find reasons to go there 2 or 3 times a week just to see her. Eventually a female friend of mine asked her out for me without me even knowing about it.
She said yes, and we started dating. Things went very well immediately, we clicked nicely. We enjoyed the same music and art and shared the same religious and political views as well. We started having sex about a month into our relationship and that made us click even more.
8 months flew by like nothing because we were having so much fun together. Our sex life was getting better and better each week. We were exploring our sexuality together and getting more and more in tune.
I had almost put my kink of dressing up in women’s clothes and shoving my dildo up my ass aside. Getting regular satisfying sex will do that to a guy sometimes. I had thought about it a few times but with Jenny and I having such wonderful sex together, I thought about it less and less each day.
One day, Jenny and I were planning a day together. I went to pick her up at her apartment early that morning. I was so early that she wasn’t even awake.
While Jenny was taking a shower, I realized that I hadn’t been alone in her room in the entire time we’d been together. I started to snoop through her drawers. There wasn’t anything in there that I hadn’t seen or removed from her body already so I quit looking quicker than I normally would.
In the days after our day out together, I started to fixate on snooping through her drawers again and I began to wonder how her clothes would fit and feel on me. The more I thought about it, the more I needed to know.
I came up with a plan to get in her apartment when she wasn’t there. She had given me a key to her apartment already but I never used it and I didn’t want to violate her trust since things were going so well with her. I just called her at work and told her I was in her neighborhood and I needed to use the restroom and I would use her bathroom. Calling her allowed me to let her know I was in there and also verify that she was at work and I had time to look without getting caught. She okayed everything.
I entered her bedroom and took off all my clothes. Jenny had almost the same measurements as my mother, just a little thinner, so I knew I’d be able to squeeze into them for the most part. I put on a pair of her underwear and strapped on one of her bras. It was tight but still felt nice on my body. I tried a pair of her jeans but I couldn’t button them, too small, but I found a sun dress that I had never seen her wear before. I put it on and it fit amazingly! I found out later she didn’t wear it because it was too big for her.
I spent over an hour at her apartment trying on clothes and feeding my kink. When I was done I raced home, put on some of my women’s clothes that I had hidden away, so Jenny wouldn’t find them, and I grabbed one of my dildos and put it in my ass and jacked off.
This started up my kink again and I found myself doing it on an almost nightly basis again. I knew that if my relationship with Jenny was going to continue, I was going to have to tell her about it.
It took me over a month to work up the courage to tell her. I was shaking and mumbling the whole way through it. My heart raced and pounded so hard that I thought it was going to explode.
To my surprise, Jenny was ecstatic! She told me that she had fantasies about being with a transgender women, or just women in general. She wasn’t a lesbian but she just wanted to have “fun on the side”. Which was ridiculously close to how I would describe what I was doing.
I took out all my women’s clothes and showed them to Jenny. She laughed hysterically when she saw them. She told me I had terrible taste and no sense of style. She was right. I had no idea what I was doing.
The next day we went to the mall and bought a new outfit that she picked out for me. We started with a new bra and panties combo. She picked out a black bra with a matching thong which I had never wore before. Then she found a cute top and a pair of jeans that fit unbelievably well! I couldn’t believe how perfect they fit and made me look incredible. Of course the girls at the store looked at me strange but they let me use the changing room because Jenny knew the girl that worked there and told her I was gay.
We went back to my place and I put the new outfit on. I felt so hot and incredibly turned on!
“Let’s go to my place, I have a surprise for you.” Jenny said eagerly.
“Ok, lemme get out of this…”
“No! Wear it to my place!” She demanded
I had never wore my women’s clothes outside of my house and was terrified to do so. After a little peer pressure, she got me to do it. I stepped out of my house and ran to my car and jumped in. We drove to her apartment and I did the same, I jumped out and sprinted to her door. Once inside her apartment I felt much better.
We went straight to her bedroom and started making out. As we were kissing, I started to instinctively groping her breasts.
“What are you doing?!” She gasped as our lips released each other. “I’m the man!” She added
She started to feel me up, pretending I had tits. She started to nibble on my neck and squeeze my ass. Then she pushed me on the bed and got between my legs and started dry humping. She started unbuttoning my jeans and pulling them down. She removed all my clothes and then removed hers.
“I’ll be right back.” She said as she climbed off me
She walked to her closet and reached inside a box. She pulled out a dildo and a strap-on. A lump built up in my throat as I knew what was going to happen. I had shoved a dildo up my ass hundreds of times by this time but I was always in control of how deep and how fast. Now I didn’t have that control.
Jenny put the strap-on on and stood in front of me. Her duck was bigger than I was used to. It was at least 10” and thick! She climbed between my legs in a missionary position, squirted a glob of lube on her dildo and pressed it against my hole. She started to slowly work it in. My body started to shake. As the tip slid in my ass, I yelled and bit my bottom lip. She started slowly grinding and working it. The big rubber cock was sliding in and out much easier now.
“Get on all fours!” She said as she pulled the dildo out of my ass.
I did as she said. I got on my hands and knees and she pressed the cock against my hole and shoved it back in. I moaned loudly again. She grabbed my hips and started to thrust. Not having control of how hard I was being fucked was no longer a fear but an unbelievable turn on! She was pounding my ass much harder than I thought she would and I was enjoying every second of it.
“Holy shit I’m gonna cum!!” I moaned
Cum started squirting out of my cock without my hand even touching it! It was awesome! For the first time since I started this, I felt like a woman!
When I finished cumming all over her sheets, she pulled the cock out of my ass and laid next to me.
“Did you like that?” She asked
“Oh my god yes!!!” I said. “Can we do that from time to time?” I asked
“Whenever you want.” She answered
“I can’t believe how awesome it is to be fucked!” I said out of breath
“I know it’s awesome isn’t it?!” She said laughing “..yes, that’s how I feel after you fuck me.” She added laughing even harder now…
..to be continued
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