Meeting a Cross Dresser Ch. 01

I met her online. Sandy, a cross dresser by night and nurse by day was pretty good at passing as a woman. Our messaging conversations progressed to phone calls to our first meeting for coffee. She described her fantasy of having a sexual relationship with a transgender woman. That was what attracted her to me.

I was looking for girlfriends that would accept me as a woman. I wasn't looking to satisfy someone's fetish. Even so I felt a connection with Sandy so I took the chance. Our time getting to know each other in person was perfect. We started meeting often and I realized that I was getting the friendship I needed but Sandy needed more.

I had pieced together enough of what she had said to understand her fantasy so it was time to make it happen. I called her Thursday to set up a women's night at her home over the weekend. Saturday worked for her so we set a time. I had a mani-pedi in the morning and spent Saturday afternoon getting ready. My makeup was perfect if a bit slutty. My red lipstick matched my freshly painted nails. I chose a new black bra with matching thong, garters and stockings. I put them on covered by a white blouse and simple grey skirt. Black four inch heels put me at six-three. My hair was curled and styled as well as it had ever been. The air was a bit cool so I put on a medium length coat, grabbed two bottles of pinot grigio and headed over.

She greeted me at the door with a beautiful smile, thanking me for remembering her favorite wine. She was wearing a sexy blue dress that came to her knees and her dark straight blond wig parted on one side. It was my favorite of her wigs. She must have spent an hour putting on her face it was so perfect. Time well spent. She hung my coat while I put one bottle in the fridge and opened the other. She set two glasses next me and I poured two generous amounts. We sat and caught up on what happened in our lives since we last met. Time was flying by and we were well into the second bottle. We topped off our glasses and moved to the couch, retrieving the cheese tray she had prepared. She had been talking about a new drama series the other day so I suggested we start watching it together. I sat on the chaise portion of the couch leaving enough room for her to slip in next to me. She picked up the remote and took my queue laying against me. We watched the first episode without moving much. I let my skirt work up my legs a bit so she could see the top of my stockings. After the second episode I asked if she minded me removing my skirt and blouse saying they were binding when I moved. She agreed as long as she could get more comfortable too. She was gorgeous wearing a matching purple bra and panties and nothing else. The sexiest part was we both had our business tucked back making our panties smooth and unassuming.

We went back to our positions when I turned a bit towards her. I put my arm across her body and rested my hand on her leg. She gave out a satisfied sigh and I knew we were properly started. I rubbed my hand along her perfectly smooth legs. She turned to me and we shared our first kiss. It was light and lips on lips only, gently trading lipstick. It is the most sensuous kiss I experienced with anyone. I moved my hand over her body to her shoulder and back to her thigh eliciting a light moan. She was exciting me and I was getting uncomfortable. I had to pull my cock out before it became painful.

"Will you pull off my thong? I need to stretch. " I requested. I lifted my behind when she pulled them down and my cock flopped out.

"Oh my" she said. I smiled at her innocence and her face reddened a bit. Worrying about having sent the wrong signal I went in for another kiss. This time though, I opened my lips and teased her a bit with my tongue. She responded quickly with her tongue. We enjoyed another sensuous kiss. She broke it and kissed my neck and shoulder. I lifted myself up a bit and without my asking she reached back and unhooked my bra. It fell behind the couch and she slid down to kiss my breasts. She teased one nipple and then the other before moving down further. She kissed her way to my navel and then put her hand lightly on my cock. I breathed in sharply when she squeezed it harder. This time she smiled at me, then lowered her head to lick the tip. I sighed lightly to let her know I liked it. I noticed before that my precum had started flowing so I knew she was tasting it.

She took me in her mouth. It was warm and smooth and the feeling of her tongue massaging me was glorious. Seeing her lipstick contrasting my skin was erotic. She started a slow, methodical blowjob. I reached over to pick up my wine and leaned back to enjoy the attention. She brought me to the edge and masterfully pulled back when I was close. She moved down to taste my balls. She massaged them gently with her tongue and mouth before moving back to take my cock. She repeated this a couple of times before taking me past my point of no return. I warned her that I was going to cum. She didn't slow. She instead increased the pressure with her tongue and slammed her mouth down to my base. That was it for me.

"Oh baby I'm coming!" I think I yelled it. She pulled off me.

"Cum for me baby. I need it." she said. She moved back to align her tongue with the head of my cock and I started squirting my cum in her mouth.

"Ohhhh!" I moaned as she milked my cock. I came more and more. She had built my orgasm up and up so it was very strong. Her talent was apparent. She collected all of my cum without spilling a drop. After she pulled off the only evidence was my throbbing, bouncing swollen cock.

"Mmm that was amazing." I told her.

"The amount of cum you gave me was amazing." she responded.

I pulled her to me and we kissed again. Her lips were soft and her tongue tasted of my cum. What a delightful combination. I reached down her back and slid my hand under her panties. She sighed lightly and I slid my hand further. I reached her hole and teased it a bit. My finger was dry so I didn't try to get further. She suddenly got up. I was afraid I had pushed her too quickly. To my surprise she opened the drawer to the coffee table and retrieved a bottle of lube. She handed it to me and stood there waiting for my move. Taking her queue this time I reached out to pull her panties down. Her cock swung out close to my face. I liked that and went to touch it. I knew it conflicted with her desire and had planned on ignoring it but the temptation was too much. Before I could touch it she had it swung back and held with her legs. I smiled my acceptance and asked her to lay down again. She laid with her back against me and turned her head to kiss.

I broke our kiss so I could open the bottle of lube. I put some on my fingers and started rubbing her hole. She moaned in my ear. I put more lube on my fingers and leaned over to kiss again.

I inserted one finger. She moaned approval as we continued making out. I started pulling and pushing my finger in and out from the first knuckle to the second. She continued moaning her approval. Our tongues continued to dance. She moved her hand back to grab my cock. Now I moaned my approval. It was soft but her renewed interest was changing that. She ran her hand up and down my shaft. Her soft hand brought the blood back to my cock. The tips of her nails rubbed on my cock turning me on even more.

I added a second finger in her butt. She moaned her approval again. Her kiss became more intense. She sucked my tongue while I started fucking her ass with my fingers. She got into it and started pushing back harder on my fingers until I added a third. She gasped a bit and stopped pushing. I stopped too to let her adjust. I knew she needed to handle three fingers before she could have my cock. I kissed her cheek and pushed my cock against her hand. She took notice and returned to rubbing it. Keeping my fingers still I kissed her lips. She returned the kiss adding her tongue. I waited for her to start pushing on my hand before I moved it. A few minutes later she did. She pushed back until three fingers were in to the second knuckle and stopped. I pushed a little to test the waters so to speak. She met them so I started a slow cycle of pulling them out completely and pushing in as far as I could. I kept going until she started really getting into it. When it seemed like I couldn't push them too far in I pulled them out and lubed my cock.

"Fuck me, fuck me now. Please get it in me." Her voice was soft but her breathing was hard. She was excited with the anticipation of my cock. I slipped it between her cheeks but pulled back when she tried to push it in. She needed to learn my cock was in control. It would be in her ass when it was ready. She moaned and told me she needs it. I put it in her crack again and she remained still.

I slipped the head in.

"Ohhhh yeah get it in me!" she commanded. She was still tight and I wanted her to adjust a bit first. I turned her head to me and kissed her again. With my free hand I lifted her leg and her cock swung forward. I pushed my mouth passionately on her lips, grabbed her cock and thrust my cock in so my balls flopped against hers. She sighed and met my kiss. I slipped my hand up her cock while I pulled mine back so just the tip was in. I thrust forward pushing my cock to her depths again. I pulled back and thrust again.

Her ass had loosened enough that I knew it wasn't painful for her so I started a slow grind. She moaned her approval while sucking my tongue. I rubbed her cock. I used her precum to lubricate it. I knew she wanted to play the part of a cis woman but I loved holding her cock. I thrust again matching the movement on her cock. I held the skin tight pressing on the base. I held her cock while I started another slow rhythm fucking her ass. Her breathing became sharper and her leg started shaking lightly. Her ass met my thrusts. I slid my cock in and my balls slapped her ass. She moaned and pushed back. I pulled back quickly and started a slow push in. She pushed back until I was completely in again. I pulled back and she started fucking my cock. I stayed still while she moved back and forth, impaling her ass on my cock. I felt her cum flowing out over my hand and it put me over the edge. It was too much.

"I'm cumming! Ohhhhh!" I told her. She turned back so we were kissing when I came. And cum did I. My cock was throbbing in her ass. My hand was jerking her cock. Our tongues were playing. And my cock continued throbbing and shooting cum in her. It seemed like an eternity until it ended. I rested my head on her shoulder and she put hers on the couch. I didn't want to move and didn't think I could. We stayed there motionless until my cock softened and slipped out of her.

A few minutes later she fell asleep. I was still feeling the wine so I didn't want to get up to drive home. I didn't want to disturb her, then I saw her glass was still full so I sipped it while the news was on. I slept off and on next to her that night. Each time I awoke I saw her face and body. Each time it looked sexier and more beautiful than the last.

I awoke to Sandy kissing me and rubbing my cock. As soon as I realized what was happening I returned her kiss. She had been up early and redone her makeup and hair. It was perfect. She slid down to suck my cock. It was beautiful when she looked up to make eye contact. I looked at her, past my breasts to see her lips perfectly covered and lined with lipstick, her eye shadow dark and sultry now, her green eyes staring back into my soul. I felt her cock hanging on my leg. I almost shot my load then but was able to hold back. She kept eye contact while blowing me. She used her tongue and technique to make me cum quickly. It was different from last night. It was powerful but I felt overwhelming relaxation. She cradled my balls in one hand when I was close, pulled back to collect my cum in her mouth and started jerking me with her other hand. I came after a couple minutes. She milked my cock to get all the cum in her mouth. She pulled off and smiled. I could see my cum on her lips and teeth so I pulled her to me before she swallowed. I licked my cum from her lips before she put them on me. When she did she spit all of my cum in my mouth. We made out again and I let her suck half of it back in her mouth before swallowing the rest. I don't know anything would compare with last night. That was definitely competition for it.

When we broke the kiss she reminded me of her Sunday shift at the hospital. We stood up and found my clothes. I used the bathroom briefly and cleaned off makeup that was smeared. We made plans to continue the series on Friday.

I was so grateful to find someone that wanted to be with me and that I enjoyed being with. Suddenly we seemed so compatible. I thought I was supposed to find a man's man that could accept me. I guess we never know where life will take us.