Meeting a Cross Dresser Ch. 02

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Brianne's second time with Sandy.
2.2k words
4.65
12.1k
10

Part 2 of the 2 part series

Updated 06/08/2023
Created 02/20/2017
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Brian70
Brian70
171 Followers

Two weeks ago Sandy and I had spent a mind blowing night together. She had been a little distant since then so I was afraid. I was afraid we had gone too far too fast. I had been patient waiting for her to return two calls. I decided to make it three. Fuck it. I didn't really feel like I had anything to lose anymore. I called. She answered. I started shaking.

"Hello."

"Hi Sandy, it's Brianne."

"Hi Brianne! It's nice to hear you." she responded. "Sorry I haven't called. I just finished some double shifts. I haven't been doing anything but sleeping and working".

"Oh I see. I was worried that something happened to you."

"Nope, I was hoping you could come over to watch our shows together. You have perfect timing if you're free tonight." she said.

"Yes, I'd love to."

Maybe I was worrying about nothing. I grabbed a sweatshirt to wear over my tank and yoga pants. My hair was back in a ponytail, makeup was good enough and my cock was tucked back letting my pants hide it completely. I drove there carefully because I was still shaking a bit. I stopped on the way for a bottle of merlot. I actually bought two bottles making sure one had a screw top. I needed something to sooth my nerves so I parked a house down from hers, positioning the car so she couldn't see me inside. I took a deep breath, unscrewed the cap of the bottle and drank. I sat for a moment and felt the wine take effect. I took another drink. Bottoms up! Not quite but at least half of the bottle was gone. It was nice. It helped. I grabbed three pieces of cinnamon gum and started chewing aggressively. I took a deep breath, grabbed the full bottle and went to the door.

She greeted me wearing a white tank top, pink short shorts and her dark wig. She was beautiful with very subtle makeup. Her toenails shined from the light inside and I noticed her fingernails matched. She invited me in.

She thanked me for the wine and poured two glasses. I followed her into the kitchen grateful that her house was warm. I hung my sweatshirt on a stool. She had a bolognese sauce on the stove and put ravioli into water when I got there. I was thankful. I hadn't eaten since breakfast.

"It smells delicious." I commented.

"Thanks. I started it this afternoon so we could share it. I was distracted so I forgot to call you earlier." she responded. She looked beautiful. Her voice was soothing and reassuring. The food smelled fantastic. My head was swimming from the wine. I melted for her. I completely forgot she hadn't called, texted or emailed in two weeks. My pain had disappeared completely when I saw her smiling back to me. All the problems from my life fell away when we were together. She walked over to me while I leaned back on her counter. She put her arms around me and we kissed. Everything was perfect. The timer went off and she dished up salad and the ravi and bolognese. I topped off our glasses and we sat at the table. I barely remembered to spit my gum in the garbage.

We sat together on the same side to watch our TV series. Two episodes later we were finished and moved to the couch. The third episode finished and she turned to me. I had just turned to look at her. Our lips were close so I leaned in and waited. She would have to bridge the gap if she wanted it. Thankfully she did. She passionately kissed me. I returned her kiss.

We made out. I pulled back and she came forth over me. She broke off and excused herself to use the bathroom. I refilled our wine glasses from another bottle she had. She came back to me from the bathroom, naked. She swung her hips. Her cock was tucked back so I just saw her neatly trimmed bush. She smiled as she sat next to me. She put her hand on my breast and teased my nipple through my top.

"I feel overdressed." I told her. I stood up and she undressed me. My cock swung out after she pulled my pants and thong down. She pulled my tank top off and held a breast with her hand. A shiver went through me when she pinched the nipple. She rolled it in her fingers. It felt so good but I wanted more. I sat back next to her. She bent over me and licked my cock. I moaned, letting her know she was on the right track. She continued licking it, then engulfed the head.

"Oh" I moaned. I stretched my legs and she slid her mouth down my cock.

"Ohhh" I moaned again. Her mouth was warm and soft and slick. It had been nearly two weeks since I had cum, the last time we were together. Her tongue was magnificent. She licked my shaft again. I wanted to cum but she slowed down. She held back a bit longer before letting it happen. When she let me cum I shot my load like it was my first time. Two weeks worth of waiting ended in her mouth. It was one of those powerful orgasm where I felt the cum traveling from the base through my cock to the head before squirting out. I saw her jump at the first shot and settle back for the rest. She swallowed it and came up to kiss me. We shared another erotic kiss. I could taste my cum on her tongue. After we parted I saw there was a little remaining on her lip that I gently licked off.

We laid on the couch together both naked still. She slid her butt back to me pressing it on my cock. I know she was trying to get my cock up again but it had only been a few minutes. She nestled back more and pulled a light blanket over us.

A few minutes went by before she tried again. She turned her head to plant a soft kiss on my lips. Creating a space for her hand she reached down to hold my cock. I was hard in seconds. She aligned my cock with her hole and turned back to wait. She didn't try to get me in her. I pushed forward lightly to discover she had lubed before we laid on the couch. I pushed further and she moaned. I pushed again and felt my head slip in. She moaned much louder. She was too tight. My cock was squeezed but I pushed again slipping another inch in. She turned to look in my eyes. I waited for her hole to adjust.

She had been the one to put my cock there. She had lubed before laying with me. She would have to work through it to adjust. I pushed my cock in until her cheeks pressed on me. I waited for her to feel accustomed to it. I pulled back and pressed in again. She was loosening but still tight. The next time she met my stroke by pushing back when I bottomed out. I pulled out to push in again. And again. This time she started grinding on me. I stayed still and she picked up her pace. She slid her ass down my shaft. Her cheeks rubbed on me when she bottomed and ground her hips. She built a rhythm while I kissed her neck.

"Cum in me" she whispered. "I need to feel it." she increased her speed and I met her movements. Her ass was still tight as she moved back on me. I pushed in and felt my orgasm rising. She pulled away and stopped. I pushed forward, my cock entering her to its base. She moaned and I repeated the move. My orgasm was closer. I felt the pleasure starting in my legs, spreading to the rest of me. I increased the pace and her moans matched. My cum was ready and I pushed in one more time. I moaned and pulled her closer. My cum shot into her ass. My cock throbbed in her reminding me her ass was still really tight.

She pulled off to use the bathroom. She came back with a damp cloth to clean me. She wiped my cock and then took it in her mouth. She worked my soft cock with her tongue. I saw that her cock was still erect. In the past she didn't want me to give it any attention even though I had. I asked her to lay down so I could work on her. She did and I straddled her. Our cocks touched and my breasts hung down on her chest when I leaned down to kiss her. I moved down to tease her nipples. I took one in my mouth using my tongue to play with it. She responded so I teased more aggressively by biting it. I moved to the other and teased it until it was hard. I kept playing with them as I slid further down her.

I reached her cock. I licked her precum from the tip. She moaned approval so I took it further. I licked down her cock to her balls. I teased them before taking each in my mouth. I licked back to the head and wrapped my lips around it. The familiar taste of precum was welcome. I sucked her cock in my mouth taking her in to the base. My nose buried in her bush. Her cock filling my mouth. Her soft feminine scent filling my nose. I held her balls in my hand while sliding my mouth back up her cock. I got to the tip, swirled my tongue around the head before taking her in again. I repeated this and could tell she was close. I was anxious to taste her cum. It would be my first of her. I took her in again giving extra attention with my tongue. Her cock swelled and she pushed her cock towards me.

She came in my mouth. It flowed quickly and filled my mouth. I was delighted that she let me get her off. I milked her to get as much as I could. I swallowed before moving up to lay next to her. She relaxed and I could see her satisfaction on her face. She climbed over me to stand up and lead me to her bedroom. It was the first time I had been in it. We fell asleep quickly sleeping well into the morning.

When I woke Sandy was wearing a black bra with her forms, a matching black thong and her darkest wig. She was straddling me while rubbing my cock. It hardened quickly bringing her to smile her appreciation. She scooted up me enough to get my cock between her cheeks. She pulled her panties to the side, lining her hole up with my cock. She let herself sink down onto my cock. It slid into her tight asshole. She pulled her legs forward a bit so she had as much in as possible. I could see it was testing her. Her expression showed pleasure mixed with pain. Slowly her pain was subsiding and she started to ride me.

I grabbed her cock and rubbed it in time with her movements. She moved faster leaning her head back. Her ass held my cock perfectly as she rode it. Her rhythm was bringing me close to cumming. I was able to use her precum to lubricate her cock. I pressed the front of it with my thumb. She moaned and I did it again. I was on the edge and felt she was close too. I ran my thumb down her cock again. I watched it swell and her cum shot over my chest. I couldn't hold back. I shot cum into her ass. She milked my cock with her ass while my orgasm subsided. Spent, she rested her body on me while recovering.

We showered and put on our makeup, got dressed and headed out for brunch. Sandy let me borrow a dress and shoes. We had a wonderful meal and got a little shopping in. We each purchased new sets of bras and panties, a few dresses and another pair of boots. We got back to her SUV and put our bags in the back.

We climbed in the front. Before driving away she leaned to me and we kissed. Her tongue driving me crazy, her lips warm against mine.

"Recline your seat" she commanded. I complied knowing something good was going to come of it. She lifted my dress and I helped pull my thong down. She engulfed my cock in one rewarding move. She pulled my dress down to cover her head. Luckily it was a stretchy lycra dress. I watched her head stretch the dress taught as she lifted off me. I watched it shrink back as she took more cock back in her mouth. I was nervous someone would walk by. Her actions were obvious if anybody looked over. She was working my cock well. Her tongue was hitting the right spot and I was going to cum quickly. I came and she collected it all before pulling her head from my dress. She sat back in the driver's seat.

I pulled my panties up and straightened my dress before she drove us home. We made plans to get together again next weekend. We said goodbye with a soft kiss. I'm hoping she will have a chance to meet for lunch during the week.

Brian70
Brian70
171 Followers
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5 Comments
ptscuriousptscuriousabout 2 years ago

Another good story of Sex and Love involving the sort of Woman I long to meet.

xploring96xploring96over 6 years ago

Love that the full time trans woman loves to use her cock and is fucking the CD.

Brian70Brian70over 6 years agoAuthor
RE Panty Power

Sounds like good times! :=) Wish I was there.

AnonymousAnonymousover 6 years ago
Panty Power

I met a panty wearing man from a panty Web site. We meet once a month for some panty sex. As well as panties we wear stockings, suspenders and basque for our fun sessions. Great to rub cock against cock, suck each others cock, wank each others cock and shoot our cum on each other. Have yet to try anal but that will probably happen eventually.

AnonymousAnonymousover 6 years ago
Panties

I love wearing panties and thongs!

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