I got stretched, Pt II

I had been living a double life and now it had come out in the open.

I had been dating this girl, Michelle for about 6 months now and for the most part things were pretty good. Our biggest problem was that I was also living a second life, as Stephanie. My cross dressing gay side.

My gay side started coming out early on, 8 or 9 years old when I met my friend Jayson. He is a very feminine guy that I grew up with and over the course of our childhood, we progressed from fooling around as young, curious boys do, to full on gay sex. I always topped him and more or less considered him my girlfriend.

Eventually that wasn’t enough, and I began a sexual relationship with Jo, a guy that lived a couple houses down from me. Jo was the first guy I let fuck me in the ass, and my relationship with him was where my desire to dress as a woman and be fucked would come to fruition. I started wearing womens clothes when I was just a boy when I’d steal my moms underwear and whatnot. I let Jo fuck me because they our fooling around I knew he had a small cock and I was always hesitant of letting a bigger dick inside me.

I met Nicholas, Jo’s cousin and everything changed. Nicholas was the first male I was ever attracted to physically. It wasn’t just about sex, I was actually attracted to him. When I got him in my bedroom though I found he had a huge 9” bird in his pants. I did what I had to do though and took it like the little bitch I am. All of it you can read about in part 1.

The day after Nicholas and I hooked up I received a voicemail from him explaining why we can’t go on doing this. He wasn’t gay and I claimed I wasn’t either and even though we had a night of great sex, he just couldn’t be with me.

I was really bummed out about this but I understood what he meant. I went into a major spiral of depression for about 3 solid months after. Nicholas being a big part of that but also I was really tired of hiding my double life. It tore Michelle and I apart and I was feeling very alone. I found myself living as me by day and Stephanie by night. I’d go to work and come home and immediately get into my women’s pajamas and watch movies.

After a few months of feeling very down, I decided to try and pull myself out of my pit. I’d go out and try and meet someone new! I had no luck for a very long time. Oh there were girls that I’d meet at parties or other social gatherings that I hooked up with and guys that Stephanie would bring home and have sex with but none of them were real connections.

I did a lot of soul searching and realized what I really wanted and more importantly, what I really needed.

I met Ashley one night a cousin’s house. She was the friend of my cousin’s girlfriend. We agreed to go out and to my surprise, we hit it off really well. At first glance, Ashley wasn’t really my type. She was athletic and slender and not a lot of curves. She was as tall as I am and weighed just a few pounds less than I did. Nevertheless we hit it off and I was finding it easy to talk to her on a personal level and decided to proceed with the relationship.

We had been dating for about 3 months now and it was going really well. We we’re getting along great and starting having sex, and it was incredible. She was kind of aggressive and liked to take charge in the bedroom which was exactly what I wanted from a woman!

One night Ash and I were apart, she was with some friends and I had decided to stay in and play some video games as my gaming had slowed down quite a bit since a new girlfriend was in the picture. After an hour or so of gaming I became bored and restless. I started walking about the apartment thinking of something to do but came up with nothing.

I opened my closet and found my small dresser I had hidden in the back of my closet that had all my clothes, lingerie, makeup, wigs, my fake breast chest piece, and my dildos. At first I just started sifting thru my stuff and looking at it. I hadn’t dressed up since I met Ashley.

My curiosity got the best of me and I decided to just put on some panties and a bra. I had two different size bras, one big one for when I wore my chest piece and one small one when I didn’t. I was wearing the small one this time. After clasping the bra, the sexy feeling I get when I dress up started to come over me. So, I put on a long blonde wig and some lipstick and did my eyes. By now I was fully turned on. I pulled out my little black dress and some black stockings and put them on. Strapped on some heels and I was fully dressed. I stood in front of the mirror and was so turned on. I grabbed one of my dildos and started sucking on it. It wasn’t enough, I wanted a real cock in my mouth!

It wouldn’t hurt to go out would it? Of course not, there was no guarantee I’d find a guy and if I did then so be it. Ashley and I aren’t married.

I went to the gay bar that was a few blocks away and sat at the bar and ordered a few drinks. A few drinks became a few more drinks and I had a few hits but nothing striked my fancy. I decided to go home without hooking up with anyone. When I got home I took all my clothes and climbed into bed. Normally I would just go to bed but I felt like even though I came home without a guy, it didn’t mean I had to go to bed unsatisfied.

I grabbed one of my favorite dildos and began toying my ass a bit before shoving it balls deep inside my hole. It was only a matter of seconds before I shot a hot load of cum all over my stomach.

I jumped in the shower and cleaned up and instead of sleeping in my boxers as I had been doing since meeting Ashley, I decided to put on another pair of panties, and my cute girly pajamas. I crawled into bed and slept better than I had in a long time.

I woke up to my phone ringing and it was Ashley. I had completely forgot that we had plans this morning. She said she was at my door knocking but I was sleeping so well I didn’t hear it. What’s worse is I was so groggy walking to my door that I completely forgot I was wearing my girly PJ’s and panties. I opened the door and Ashley’s jaw dropped.

“What. The. Fuck?!” Ash said

It was then I realized what was going on.

“Oh.. shit! I can explain if you let me.” I begged

Ashley agreed to come in and sat on my couch. I had only been with her 3 months and even though I liked her a lot, I knew from my experience with Nicholas that I wasn’t going to be the end of the world if she dumped me and I was dead tired of living a double life. So I decided to just be an open book. I told her everything, and I mean everything! EVERYTHING!!!

Just as Nicholas had been accepting of me when I sprung Stephanie on him, Ashley was as well. She seemed hesitant and confused at first but as I further explained she became more open and explaining some of her kinks as well. She explained about her need to take charge in the bedroom and how she has always dreamed of being with a woman but never had the courage or opportunity.

I decided to go to my room and come out about 15 minutes later and reveal the full Stephanie. Again, her jaw dropped. I had my chest piece and everything on.

“Christ, you look more like a woman than I do!” Ash said with a laugh.

“You’re not freaked out?” I asked

“A little shocked but nothing to worry about.” She answered as she got up and kissed me. “Hmm, that’s what it’s like to kiss a woman? I could get used to this I think.” She added

After a month of so we decided to go to a sex shop. Not with an agenda just browsing. While we were there, Ashley found a strap on that she wanted. It came with a 7” dildo and a vibrating part that the girl inserted so both partners would receive pleasure.

“We should get this!” She said quietly but excited. “I wanna use this on Stephanie!”

I was shocked that she wanted to incorporate Stephanie into our sex lives.

“You do?” I asked

“Obviously Stephanie is a part of you and your life, if I’m gonna be with you then she has to be part of my life as well.” She explained

We bought the vibrating strap on and raced home. The entire way home we talked about sex and things we wanted to try and do to each other.

“My cock is rock hard babe!” I said

“Mine too!” She said laughing. “Take yours out, I can’t wait to get home.”

I did as she asked, I pulled my cock out and her cold hand grabbed a hold of the base of my shaft and she started stroking. I couldn’t focus on the road very well but it should be considered a miracle that I, one, got us home safe, and two didn’t cum all over the place.

“Go get dressed in something sexy!” She urged as soon as we closed the front door.

I ran to my bedroom and grabbed my platform stripper heels, a pair of black thigh high stockings, a pair of black lace panties and a garter belt to match. I was so excited and nervous that I was sweating and my chest piece was struggling to fit. Eventually I got it on and put the 40DD bra on over it. I started putting my make up on which also took longer than I wanted to. I chose the same blonde wig from before and put Ashley’s silk bathrobe that she leaves here on covering me up.

I took a deep breath, gave myself one last look in the bathroom mirror and opened the door. I made my way to my bedroom and opened the door. Ashley was standing there wearing a pair of my mens jeans, a pair of my boxers, one of my favorite t-shirts and baseball hats. She had drawn on a fake goatee with an eyeliner pencil and tied her hair up to look less feminine.

“Hey Stephanie, I’m Andy.” She said

“Oh my god this is weird but so fucking hot!” I yelled out.

We laughed together for a second and then Andy leaned in to kiss me. It started very cute and pecking kisses but didn’t take long before we were slobbering all over each other. She untied the bathrobe and it dropped to the floor. Her hands began to caress my tits and she kissed my neck. She reached around and unhooked my bra and let my big fake tits fall out. He lips and tongue made their way down to my nipples and she sucked and nibbled on them. I used this time to shimmy my way out of my panties and kick them aside.

As we aggressively pressed our bodies together, I could feel that she was already wearing the strap on and dildo. So I got down on my knees, unbuttoned her jeans and pulled them down to her ankles. Her thick fake 7” cock stared me right between the eyes.

“You gonna suck my cock or stare at it all night?” She asked sternly

I grabbed the base of the cock and inserted it in my mouth. She turned on the vibration and let out a moan as the g-spot tickler started going to work. Sucking a dildo certainly isn’t anything close to sucking a real cock but this was still pretty damn hot.

“Bend over you little bitch!” She demanded as she pulled her cock out of my mouth and pulled me to my feet.

I got on all fours on my bed and she positioned herself behind me between my legs. She smacked my ass a couple times as she began to spread lube all over her cock.

“Oh wow! That feels amazing!” I moaned out

I thought she was using her finger to spread lube on my hole but when I lifted my head and looked back I saw her licking my hole! I had never had anyone do that for some obvious reasons of course but this felt so unbelievably insanely amazing! No way I was gonna stop her!

Shortly after I felt the familiar feel of a finger spreading lube on my ass and then her cock pressing against my hole.

“I’ve never done before so just tell me what to do.” She said nervously

“Just push slowly until the head pops in then stop… 1,2,3, go!” I said

She pushed and then pushed a little hard and as I pushed back, the thick tip of her cock slipped inside my hole. I moaned out in a mix of shock, pain and ecstasy.

“Are you okay?” She yelped

“Yeah, fuck me, I can take it!” I cried into my pillow.

She began thrusting slowly at first. It felt great! I could feel the part she inserted in her wet pussy vibrating in my ass. All I could think about was if it felt this good on my ass, it must feel 10 times better on her pussy. I wanted a pussy so bad!

After a few minutes of her fucking my ass, she began to pick up the pace a bit and moan and cry. All of the sudden I felt her pull out of my ass. I turned and looked back and she was hunched over crying out in ecstasy. Her hand was holding the strap on to the side and her other hand was vigorously rubbing her clit. Shortly after she sprayed all over my legs and ass. She had squirted everywhere! As she calmed a bit she shoved her cock back in my ass.

“Oh fuck!” I moaned

“Shut up and take it bitch!” She yelled as she began pounding me again.

A minute or so later, she pulled out again and again she sprayed every where.

“Roll over!” She demanded

I rolled onto my back and she undid her strap on and threw it on the table next to the bed. She straddled me, placed the tip of my cock which was already dripping pre cum against her soaking wet pussy and sat down on my cock. It felt strange to have her grind on my cock while I was still Stephanie but I wasn’t about to complain.

“Oh fuck baby, I’m gonna cum so hard!” I yelled out

“Me too! Do it! Cum inside me!” Ashley cried out.

She began moaning again and tensing up. At the same time I shot a fresh batch of hot cum deep inside her pussy! Her hand began choking me as we came together and I didn’t care, this was the hottest orgasm I had ever had!

Ashley ended up spending the night and she slept in a pair of my boxers and nothing else and I wore a silk nightgown and a pair of panties. We woke up and had much more conventional sex in the morning but still dressed as Stephanie and Andy so to speak.

We are now a year into our relationship and it is amazing! Our sex life is incredible and we’re both very happy. I have asked her to marry me, she said yes. We will have a wedding and then have a second unofficial wedding with our friends (the ones that are accepting of our lifestyle) for Andy marrying Stephanie as well.

I have always said that I was straight despite all my gay sex and this is why. I found exactly what I need and it was in a woman. I’m not gay, just weird haha.

🔞 Candy.AI 🔥 AI Sex Chat - Roleplay, Erotic Stories, Try for Free 🕹️

Please, Rate This Story:

(average: 4.88 out of 8 votes)