I started cross-dressing when I was younger. I had shared it with no one until I was discovered by my girlfriend one night. Until that point I had kept it all hidden.
It all started when I met Linda at work. I worked at a local hospital and Linda was a traveling nurse. She had been at the hospital for about a week and we flirted back and forth but I never expected anything to go anywhere. I finally got the nerve to ask her to dinner and she instantly accepted. During dinner she admitted to me that she found me hot and was hoping I would ask her out. She is 24 yrs younger than I am. That night we went back to her hotel room and had some of the wildest sex I had ever had. The next day she moved out of the hotel and into my home. She stayed for 3 weeks. She had traveled all over the country but decided she was going to keep coming back so we could be together. What kept her from moving permanently is that she has 2 kids back home.
I gave her a key to my house so she could come and go as she wanted. She would be here for 3 to 4 weeks and hen gone for 3 or 4 weeks. This went on for 2 years. I found a hiding spot for all of my women’s cloths when she was here and took them all out when she was away.
She had been gone only 3 days. When she wasnt here I always slept in a nighty or just panties and this night was no exception. I was wearing a lacy thong to bed. It was around 2 in the morning when I felt her crawling into bed. I woke and was startled and asked why she was back so soon. She kissed me and told me her ex had taken the kids on a two week trip so she decided to come back. She snuggled close to me and her warm smooth skin next to me felt so good. She kissed me again and run her hand to my cock. I hadnt even thought about my having panties on until that second and a wave of panic rolled thru me. At first she thought I had bought a pair of silk underwear and liked how my hard cock felt thru the material. Linda loves sucking cock so after a minute she slides the blanket off and moves down to begin sucking me. That is when she noticed the lacy ruffles on the panties. She rolled over and turned on the lamp and saw that I was wearing a pink thong. I had bought this pair because it matched a pair that she wore.
“Are you wearing my panties?” she asked.
Now was the time to come clean. there is no way hers would fit me so I started with the truth. I felt like my face was as red as a fire truck.
“No babe these are mine. I am a cross dresser and love wearing women’s cloths.”
She started running her fingertips over my hard cock and stared at it for awhile and then smiled.
“That is fucking sexy,” she told me.
She had endless questions about my dressing and the entire time she was running her fingertips over my hand cock to the point I had precumm dripping and making spots on my panties and she loved that. She had me model each and every peace of womans cloths that I own. I saved what I thought was the best. A lacy black baby doll that had a crotchless panty and garters and nylons. I walked out of the bathroom with this outfit on and it only took a second and she had my cock in her hands and then in her mouth and sucking me. I have to admit that sharing my dressing and having sex had me very excited and it only took about a minute and I shot my load in her mouth and she swallowed every drop. She loves my dressing.
At this point she insisted that we go to the 24 hour Walmart not far from the house so she could by me even more cloth. We spent an hour and she bought me so many things from sexy lingerie to dresses and shoes and purses. When we got to the house again it was about 5 am she told me she had an errand to run and she wanted me to get all of my cloth out of hiding and put in the dresser and closet and when She got back she wanted me to be wearing the matching panty and bra she had bout me and the new heels and the micro dress she bought me. I was happy to do as she asked.
First thing I did was change and then started getting my closet organized and also my dresser. I had all my cloths put away and called off work and was sipping a glass of wine when I heard her pull up. I met her at the door and I tried to stand back so anyone passing wouldn’t see me but she pulled me to her and kissed me with the door wide open. She took a sip of my wine and lead me back to the bedroom. She had me lie on the bed and went into the bathroom. The lights were low in the room and it took be a second to realize as she walked out of the bathroom that she had a big bulge going down the leg of her jeans.
She crawled onto the bed next to me and kissed me. She told me that from now on when I was dressed my name was Brandy. My heart was pounding so fast. She undid her jeans and a big cock popped out. She led my hand to it and even though I had never had a Bi thought in my life, I enjoyed slowly stroking her cock. She closed her eyes and laid her head back and I heard her moans of pleasure.
“I have always wondered what it would be like to be the man,” she whispered as she put her hand in my hair and pushed it toward her hard cock.
“Suck it baby”
I did as she told me and began to suck her wonderful cock. Her moans of pleasure git louder and then her hips started moving and she was fucking my mouth. She was fucking harder and I was sucking harder. I could hear my slurping as I sucked her cock. I was shocked and excited when she started cumming. She pushed my head down hard on her cock and moaned loudly as her entire body had spames of pleasure. I continued to gently suck her cock as she caught he breath.
:Fuck, that was awsome.” she said.
She rolled out of bed and stripped her cloths off and began stroking her cock. I hadnt noticed before but she had set a bottle of lube on the nightstand. She put some on her cock and stroked it and then told me to get on my hands and knees and bring my ass to her. I didnt hesitate. Iwas amazed at how good her fingers felt going in my ass as she lubed it up. Then I felt the head of her cock softly pushing against me. I wanted it bad at this point so I relaxed as much as I could and started pushing back. I felt it slide in me and she stopped but I kept pushing and felt her cock spread me and I loved it. I was surprised when she told me that I had it all in me. It was a big cock at least 9 inches. She started slowly pumping it in and out of me and then began faster and faster.
“Fuck me harder.” I told her and she ponder that cock in me. After a few minutes I could feel I was going to cumm and I told her. She didnt slow down and shot my cumm all over my panties. I felt weak and collapsed on the bed. She laid on top of me with her cock buried in me for a few minutes. I hated it when she finally pulled out. She took my panties off of me and put them in my mouth to suck my cumm out of them.
We got in the shower together and she fucked me again with he cock. Then we got all washed up and went to bed. She picked a pair of black lacy panties to have me wear to bed. She kept her cock on. A few hours later I was woken by he feel of the cock going into my ass again and then I felt her mouth on my cock sucking it hard. She was fucking me with her cock using her hand and giving me a blowjob at the same time. When I cumm I didnt think I would stop and she let it all go into her mouth. When I stopped cumming she kept sucking until she had it all. I was very surprised when she turned and kissed me and let all of my cum slide from her mouth to mine. It was a lot and I enjoyed every drop.
Since hat time we have bought many new toys in many sizes and shaped. My favorite is a double headed dildo that is about 16 inches long. She will put in in my ass and her pussy at the same time until my ass is next to hers and we take turns stroking my cock and let the cum shoot all over and wipe it with our fingers to eat it.