Transexual Encounter Ch. 02

It had been a while since I had first seen this slim sexy TS, she was so sexy I thought about her quite a bit. My company had laid me off a few months after my encounter with her. I was still comfortable since I saved and had a decent severance package, but I was antsy about getting back to work.

I looked around for things that I normally wouldn't have considered. I came across an opportunity to do some temporary consulting work in the field I was well versed in as a 1099 contractor. As I scoured jobs boards, I saw an opportunity that would put me back in my mocha gurl's city for a few days; I had to go meet the people for an interview and proposal. I booked a room not too far from her house in hopes she would be available.

I told her about my plans and made arrangements to get in early the day before my meeting. I arranged to meet her. This time I asked her to come to my hotel, she said OK but I would need to pick her up. I told her if she was OK with it, she could spend the night. She said she might but had to figure a few things out. I didn't press her.

I picked her up and she came out looking pretty, a skin tight black leotard type pants and a tight shirt with a loose jacket as the weather was nasty cold. I know the size of her thick long cock and I was totally amazed at the fact she had tight pants on and there was no bulge at all.

We headed off to my hotel and I mentioned about going out to eat and she said she didn't dress up enough to go out.

She said to me "you should have told me about dinner, I would have sent more time getting sexy"

I told her she looked fine but she balked and we drove on. On the way she wanted to stop and get some things. I asked her about condoms and lube and she said we needed to pick some up. I went into drug store and picked up a bottle of lube and a dozen Magnum condoms for her. I am waiting on line at the counter and finally get to the register to pay. I am thinking to myself as I checked out, if this cashier only knew that the condoms were for my honey sitting in the car, and that in a short time I would be taking her huge thick cock in my ass. I thought about how cool would it be to just blurt that out to her as I picked up the bag, my cock stirred and started to engorge right there. I chickened out and said nothing and left.

Back in the car, I said I wanted to get some beer and asked her what she wanted. She told me that she wanted a bottle of Hennessy. I looked over at her as we came to a red light and I looked down between her legs and I was shocked to see a huge fucking bulge pushing through her black tights. I smiled and said that she must be glad to see me.

I could not keep my eyes on the road and was actually glad to be at a red light. I reached over and felt her up through the tented material. I previously had this fucker in my mouth and ass and yet I was still amazed at it. I wanted to bend across the seat and plant my face and lips on it right then and there but the light changed. As we drove to the liquor store I continued to reach over and stoke her meaty bulge.

When we got to the liquor store I tried to get her to come in the store with me. I said no one will notice your big hard cock sticking out, we both laughed so hard it was ridiculous. I got out of the car and started to walk to the store, and then I turned around and opened her door and bent over and kissed her on the lips and held my lips against hers and reached down and stroked her cock a few times. I released my lips from her and I could see she was flushed and I had delivered the desired effect on her.

I said don't go anywhere and don't do anything I wouldn't do, I'll be back in a couple of minutes.

She laughed and said to me. "When we get to the hotel, you are going to pay for making me so fuckin horny; your ass will be mine."

I said to her, "it already is."

Back in the car and back to the hotel. She was worried about going in together but I told her, it's my room and I can have a guest here if I want and if they don't like it, fuck them!

I had a suite with a living room and small kitchenette, she sat on the couch and I put the beer in the fridge and took one out and poured her a drink from her bottle. I brought her the drink and sat next to her. We sipped a bit and chit chatted. I told he there was a Friday's restaurant on the other side of the parking lot literally a hundred feet from the side door of the hotel.

She knew what she wanted and so did I. I was going to run across and order the food and come back and we would eat in the room, she said she would put on something sexier. I told her I needed one for the road. I finished my beer and instead of getting a beer, I put my face between her legs as she sat on the couch and I nibbled through the material of her tights, she had re-tucked herself to walk into the hotel.

She lifted her ass off the couch to "free willy" so to speak. I moved the coffee table away and knelt on the floor between her legs and pulled her tights down around her ankles. She pulled her panties aside and it popped out in all its glory. God, I never get tired of thinking about it, talking about it and writing about it; that big thick long juicy meaty fucking cock of hers.

I opened wide and put my lips around it and bobbed my head up and down on it. It grew immediately in my mouth and was less than a minute and it was fucking huge and so frigging hard, I was jealous of it but also in awe of it and happy that for tonight it would be all mine. I knew from past experience I was not going to make her cum quickly so I knew I had to break it off and go get the food. I was hungry and we had all night.

I came up for air and took the tights off her ankles and saw some cute multi colored socks she had on. I took them off her feet and saw some pretty red painted toes. I have an unbelievable foot fetish that she didn't know about yet. So I took her toes in my mouth and sucked each one like it was a little cock. I counted them off one through ten.

Then I rubbed her feet on my crotch, and I said, "I guess it was ten for the road." I kissed her once and said I had to go get the food.

I headed for the door and she stood up and said to me, "come here for a second."

I walked over to her and she said to me that she was really attracted to me and kissed me on the lips. She put her arms around me and we French kissed, intertwining our tongues. I wrapped my arms around her and held her tight to my body and told her that she was the most beautiful person that I was ever with in my life.

I told her I'd be back as soon as I could and went to get the food. The restaurant was busy and getting the order to go was taking a while. Finally ordered and it was going to be 20 minutes to get food so I quickly went back to the hotel. Would the girl who took my order be shocked to know that 5 minutes before I was giving her the order, my gurl was giving me her cock in my mouth? In a few minutes it would be back in my mouth.

Back in the room, she was in the bathroom when I came in so I grabbed another beer and drank a big gulp. I was still nervous, even though I was already with her previously. She came out and I told her it would be twenty minutes and I didn't want to be away from her for that long of time so I came back.

She smiled and said, "How do I look?"

She had on a sexy outfit that made her look like a dominatrix but not over the top. She was sporting a black bustier, black panties and fishnet stockings. I said she looked like a million and that it looked like she was going to be in charge in that outfit. She said she had plans that included me being her bitch all night long and I might as well start now.

She sent me to the bedroom and told me to put on my lingerie and heels and then come out to the living room. I stripped and put on my black thigh high stockings and garter belt. I went with a smooth lime green sports bra that held my big nipple silicone breasts tightly to my chest. The nipples poked right through the soft spandex fabric, the main reason I purchased that bra. I really wasn't a sports bra because it had no padding but the design was the same; all the better to show off my tits I thought to myself.

I didn't have time for the wig so I slipped on some black leather pumps and strutted out to the living room and told her I was at her service.

She liked the lime green bra and felt up my tits and squeezed the nipples and I pretended that I felt her doing it. I said to her "ohh... squeeze them harder." Then I moaned as if I could feel her pinching them.

She said to me," well it is apparent to me that that you are submissive little thing with a foot fetish."

I said yes Miss, I am and I do.

She put her foot up on the coffee table and pushed my head down, I got the gist. I knelt down and started kissing and licking her foot through the fish net stockings. I tried to lift her foot and put it in my mouth but she held it firm to the table so I kept kissing and licking. I tried to work my way up her leg to her crotch, but she kept pushing my head back down top her foot. I was rock hard and she knew it. I was stroking my cock and kissing away. She switched feet and I didn't skip a beat. I kissed and sucked away, I loved every second of it.

She took her foot down and stood in front of me with her legs spread wide and pointed her red painted finger to her crotch. She was about half way hard already and tenting her black panties. I moved myself directly between her legs. As I moved toward her cock, she squeezed her thighs on each side of my head and held it like that, her cock was a few inches from my forehead but I couldn't get to it.

She finally let go and at the same time pushed the back of my head up and into her meaty cock. I pulled the panties aside so fast she couldn't have stopped me. The big gurl stick was in my mouth so fast, I put suction on the head and worked my way down the shaft, I could feel the this bitch stick getting bigger and harder as I went down. From previous experience I knew I had my work cut out for me.

As I bobbed up and down she moaned and thrust her hips forward as I went down on her. I was determined to get all the way down before I had to leave for the food. I opened wide as I could and tried to breathe with the cock in my mouth and then pushed all the way down. This was starting to get somewhat easier. I made it all the way to the base of her thick slick shaft that was glistening from my saliva and held it, my nose pressed against her body. She had to be impressed; I was getting better at handling this python. I came up and took some air and looked up at her like a puppy looking for acknowledgment from her owner.

She smiled and said "you are getting the hang of it; I think I'll keep you."

I said I had to go get the food. I was putting on my pants over the lingerie and slipped out the silicone tits and I heard her say "leave the bra on baby."

I put on a sweatshirt type shirt that was loose fitting and she gave me an evil grin and then said OK you can wear that, but she threw me the multicolored socks she had on and said "wear these."

Shit, I thought, there is no way I can explain that if they see them in the restaurant, then I thought fuck it, if they see them I will say my girlfriend made me wear them, it was that or she was going to paint my toes red! Yes that would do, anyone would wear these socks over getting their toes painted. Truth of the matter I would love it if she painted my toes and made me go out in flip flops.

The trip for food was uneventful, I thought about lifting my pants somehow to show off my girly socks but did not, wish now that I had.

Back in the room we ate and drank as boyfriend and girlfriend, no shenanigans. She knocked back quite a bit of the Cognac that I had picked up earlier and I slowed down on the beer. We cleaned up the mess and I went down the hallway to get rid of the trash as we did not want it smelling up the room.

Now she told me that she wanted me decked out in a sexy secretary type outfit with full make up, wig and jewelry. I opened the closet and showed her the assortment of clothes I had hung up earlier. She immediately saw a beautiful red silk robe and took it out and put it on herself and she told me how much she adored silk, it was kind of small on me and I had acquired it like most of my things from a second hand store so I told her she could have it. She kissed me and said "you are making it hard for me to dominate you; right now I want to feel your cock in my ass." I told her that I would do whatever she wanted. She said; "well let's get you dressed and we will see about that later."

I put on my corset and tightened it to cinch my waist; she picked out my black bra and red panties. I still had on her socks and black thigh highs and garter. She picked out a grey pencil skirt that was skin tight and four inches above my knees and one of my favorite tops it had super thin material, silky, stretchy long sleeve purple top. It accentuated my tits and you could see the nipples budding through the material.

I put on the clothes and did my make up like a secretary who puts on a little more before she walks out the door and heads to a bar for a drink after work. Heavier on the eyeliner and some purple and a dash of silver for the eye shadow, blended them nicely. I put on some darker lipstick to match the purple in the top. Then the wig, my favorite silver bracelet and a costume necklace with silver chainmail and beads. A spritz of perfume and I was almost ready.

She was rummaging through my girl things and making comments on my style and tastes. All of it complimentary, she was surprised to find out that my favorite store was Goodwill and most of it came from there. It is more thrilling to wear things I know another woman wore, maybe on a night out the previous owner was dancing in the clothes I now wear. Maybe she picked up a guy or took her husband home and fucked him in a skirt I am now wearing. If the previous owner knew where her things were now, that would be priceless to see some hot MILFs face!

I brushed out my wig and stood up for her inspection. She looked down at my feet and said "really?"

I still had on her socks, forgot that small detail. I told her I would only take them off if she let me keep them.

She said to me, "well I guess you have earned them."

On went with my higher heeled black Italian pumps. She said let's go back in the living room. She sat on the couch and told me to fix her another drink and bring it to her. She had on the couch with the red silk robe on and had slipped on a pair sexy black glittery kitten heels with pointy toes, different than I expected but upon further review as the saying goes, they did kind of look sexy, cute and mischievous all at once. Yes I thought to myself I like them, maybe it will be my next purchase?

I sat next to her and we talked a bit and she told me she was worried that she was beginning to like me too much and that she was afraid that I would not want to be with her the way she wanted to be with me. She said that she wanted to be my only girlfriend outside of my home life which she knew would not change. She said as long as I was hers she would be happy. I told her that I was not seeing anyone and since I met her I thought about her all the time anyway so I was OK with it. She smiled and I could swear I almost saw a tear; I almost teared up myself as I was taken by surprise. I kissed her softly and said yes that I would only see her.

She breathed heavy and we made out on the couch like two high school teenagers. I slipped my hand between her legs and I deliberately ran my fingers up and down her shaft with an open palm as if I was stroking a woman's clitoris. She noticed and was humping my hand and grinding her pelvis. There was no mistaking her freakin bulge for a clit however. I cupped her tits that were out of the top of her bustier and put her nipple in my mouth and sucked as I slipped her panties to the side with my free hand and put my fingers around her shaft and stroked slowly up and down. She was breathing heavy and moaning and I moved my mouth off her tits and kissed the soft dark skin of her neck as I made my way up to her mouth.

We locked lips like we did before I left to get the food. This time was different, she was frenzied and kissing and sucking with a much higher level of intensity, I was kind of hanging on for dear life. She was moaning and saying how much she loved what we were doing and that her last boyfriend would never do what I do for her. I was a bit surprised but kept sucking on her tongue and taking in her juices.

We broke lip contact and I rested my head on her chest, my wig hair was all over the place but I felt the need to press my face against her body.

After a minute I slipped my hand around her semi-soft hunk of meat and stroked it, I could not bear the thought of it growing unless it was in my mouth so down I went. She said I want to video you sucking me and grabbed her phone. I didn't flinch and continued to suck up and down trying to do my best porn star imitation. I sucked the head, licked the shaft, my favorite, sucking her balls in my mouth imagining the growing amount of semen filling up in her balls.

By now I was back on the floor kneeling between her knees as she ran her phone cam. I sucked away taking brief moments to breath. I made it all the way down on her several times, each time holding it a bit longer. I could feel her shaft all the way down my throat, I still gagged but not as much, maybe someday I will be a deep throating whore that she will pimp out for cash.

She pushed me off her cock and said, I need that fucking smooth ass of yours! She grabbed my stiff cock in her hand and pulled me along by the cock to the bedroom. She matter of fact tone of voice like she was giving a command to a dog, she said, "up on the bed on all fours and show me that ass."

I knew what was going to take place and unlike the first time I met her I knew I would be able to take the length and girth of her womanhood is my ass. I had cleaned out as usual and used a big dildo before I picked her up so I was stretched out enough so it would be easier to have this torpedo in my pussy.

She stroked herself rock hard as her other hand rubbed my ass as she marveled at how smooth the skin on my ass was, she even said she wished her ass was this smooth. Hard as a rock, she slipped on the magnum condom and put the head of her cock against my pink little button of an ass.

She squeezed some lube on my ass and rubbed the head of her cock up and down the crack of my ass and then settled down right on my rosebud. I asked if it was OK that she could hold her cock in place and let me back onto it like we did last time until I am on her and then when I give her the go ahead she can thump my ass like a fucking bitch slut. That got her going and I backed onto her. Her hot thick head pushed its way past my ring and into my ass. Slowly I backed onto the seemingly endless shaft. A bit more lube a few times and I was all the way on her thick, long, hard shaft. I reached behind me and tried to pull her hips towards me and she picked up on it and grabbed my hips and pushed all the way into me, getting the last half inch of her glory all the way into my body.

I said to her "baby I am ready to be your only piece off ass and you will be my only gurl. Fuck me now, fuck me long and hard and I will be yours"

That got to her as her previous conversation was weighing on my mind so I took the chance and blurted that out. When she said yes and started to fuck me. I repeatedly said, "I love how you fuck me." I said that about ten times in a row as she plowed my ass thrusting in and out.

Then instead of repeating that I said once as she pounded away, "I love you." She grabbed my hips harder and pushed all the way in to my ass as far as she could go and held her rock hard 8 ½ inches in my ass. She finally relented and went back to fucking me.