A Scottish Lady

Why are men's clothes so boring? You look at what women can wear, and there was no comparison. The feeling of a pair of silk stockings against your skin, was heaven to me. As you may have guessed, I'm a crossdresser. My female name is Maria Stephens.

I'd always enjoyed, putting on ladies clothes. It started when I was young, and I'd wear my mums stuff. It wasn't what you would call, sexy, but I loved roleplaying as a female.

Eventually I left home, to join the forces. My crossdressing was now put on hold. During my time in the Air Force, I meet my future wife. We were married, when I found out, I was to be posted overseas.

I left after doing twenty two years, and we'd settled up in Scotland. We had two girls, and a boy, and we were so happy.

It was then that I started my crossdressing again. It was my little secret, no one else knew. I used to place an order for outfits, at least once a month. It was a thrill, to try something new on. At first I'd buy fairly conservative clothes, but eventually ordered more daring outfits. By this time I'd bought a breastplate, and it was my best investment. I could now wear low cut dresses, that showed my cleavage off.

I started taken photos of myself, on my phone, and I really liked what I saw. It was then that I started posting, on a crossdressing message board. When I started posting my pictures, I got some great feedback, and received plenty of pm's for meet ups. You may not believe this, but I still thought of myself as straight. I never posted pictures with my face in it, as I could still see my male side. My body was definitely fem, but I couldn't say the same about my face.

Eventually I posted less on there, as I'd found a social network app, called kik, where I could live chat with fellow ladies. I even joined some straight groups, and got plenty of offers when I posted pictures. The guys actually thought I was a female. Eventually I left those groups, as I felt like a fraud, having to lie.

My favourite group, was a Scottish one. It wasn't just crossdresser, that were in the group. Once again, I was getting plenty of offers. By this time though, I was becoming curious , about what it would be like to meet up. I'd bought an anal vibrator, which I loved to use.

One guy, Ross, was really keen to meetup, but I always said I couldn't do it. He was in his twenties, and was very handsome. We had some lovely chats, with him wanting to know more about my crossdressing. He loved how I dressed, as it was very feminine.

My wife was going to visit her mum, down in England. I couldn't get time off work, so she went with our youngest. All our kids, had left home by now. Ross asked if I'd like to meet up for a drink and chat, no strings attached. After much pursuance , I agreed, but it had to be at my house. I'd not been out dressed, apart from the odd drive around in my car.

It was the day of my meet, and I was very nervous. I relaxed during the day, dressed in my new mini dress. Ross text me, asking if I was still OK for tonight. I told him I was, but was very nervous. What if I wasn't quite what he was expecting, when we were face to face. He assured me, that everything would be fine.

It was that time to get ready, as Ross would be arriving in about two hours time. I started running the bath, then got to work on what I'd be wearing.

The first thing I had to decide, was what dress I was going to put on. I had so many to choose from, but settled on a black lacy dress, that came above the knees. It had a lovely low cut neckline, so I picked out my E cup breastplate. For my underwear, I picked out a black gaff, which would allow be to tuck my cock out of the way. I started call it my clit, and my ass hole, was my pussy. I'd bought a matching bra, and suspenders set recently, so I got them out on the bed. To finish my look off tonight, I'd be wearing black stockings, and a pair of 5 inch high heels. Everything was laid on the bed, so I finished running my bath, and lay in it, enjoying the heat.

I got out the bath, and dried myself. Before putting on my clothes, I shaved my legs and my crotch area. Now that I was hairless, I put on my gaff, then my suspender belt. I enjoyed the feeling of putting my silk stockings on. Once they were fastened to my belt, I then put on my breastplate. It looked hot, when I put my plunge bra on. The dress fitted me perfectly , and showed my cleavage off. I pulled the zip up, on the back of the dress. Once I had everything on, I started doing my makeup. I loved my new red lipstick, and applied some eyeshadow. Looking in the mirror, I was very happy with the result. I put on my jewellery , then stepped into my high heels. I then headed downstairs, waiting for Ross to arrive.

It wasn't long before I got a text off him, to say he'd pulled up in his car, outside my house. I told him I was ready, and to come on in. Still feeling nervous, I opened the door, to greet him.

He came in, and kissed me on the lips. It was the first time, I'd ever kissed another guy. I closed the door behind him, and turned to face him. He was wearing a white, loose fitting shirt and black trousers.

"Pleased to meet you at last Maria."

He then gave me another kiss, and put his arms around my waist, pulling me into him.

"Likewise Ross, though must admit, I'm feeling pretty nervous."

"You look so hot Maria, even better in real life."

"Thank you Ross, can I get you a drink?"

"I'll have a beer, if you have any."

"I'll get us both one."

I handed him a beer, then headed into the conservatory. It was dark outside, and I'd turned the lights down low.

"Please take a seat, and I'll put some music on."

He sat on the sofa, and I put some background music on. I sat down beside him, and we got chatting. We were getting to know each other, and he was putting me at ease. My nervousness had gone by now. I was loving chatting with this hot guy.

"Let me get us another drink."

I headed to the fridge, to get us another two beers.

"Let me help you."

He came behind me, and started kissing my neck, his arms around my waist.

"You smell so nice Maria, I love that perfume."

His hand moved to my breast, and started caressing me. I turned round, and he started kissing me opened mouth. I could feel his tongue, exploring my mouth, and I responded in kind. My arms were around his neck, his were now on my ass. I could definitely feel his bulge.

We returned to the conservatory with drinks in hand. His hand was now resting on my thigh, as we chatted some more. I put my drink down, and looked into his eyes. Moving closer, I gave him a passionate kiss.

"You taste so nice Maria."

His hand moved up my thigh, until he came to my suspender belt.

"Hmmm, I like that, I wouldn't mind seeing what you are wearing underneath that dress."

He started kissing my neck, as his hand moved higher. I opened my legs slightly, and his hand moved slowly to my clit. He was rubbing me down below, and I was certainly getting turned on.

"You are one hot lady," he whispered in my ear.

My hand moved onto his thigh, and he opened his legs. I turned towards him, and we started kissing again. My hand slowly moved towards his crotch. It was now resting on his cock, and he felt hard under my hand. My fingers traced along his length, and it felt pretty big.

"Would you like to go upstairs? I asked him.

"I would like nothing more Maria."

We headed upstairs, his hands on my ass, as we ascended the stairs. I took my time, enjoying his hands on me. Entering the bedroom, I switched on the beside light. He came behind me, and started playing with my tits, while he rubbed himself up against me. My head went back, as I let out a moan. He slowly pulled down the zip of my dress. The dress feel onto floor, so I stepped out of it. Turning around, he could now see what I was wearing underneath.

"Fuck me, that looks so sexy. You have some body."

We started kissing again, his hands on my flesh. My hand moved down to his bulge, and it felt huge.

"Someone seems turned on," I whispered, as I started biting his earlobe.

He started undoing my bra and let it fall to the floor. I sat on the bed, my legs wide open. He moved closer, and he slower removed his shirt. My hands started touching his chest, then moved down to his torso. I started kissing his six pack, my tongue exploring his navel. I undid the belt on his trousers, and slowly pulled down his zip. My eyes were level with his bulge. I undid the button on his trousers, and they fell to the floor. He had tight white boxers on. I started stroking him through the material. Pulling down his boxers, his cock was now fully expised. It must have been about 9 inches long.

"God, your cock is amazing."

I started stroking him, as I stood up. Again, we started kissing, his hands all over my body. One hand was slowly rubbing my clitty. I was very hard by now. He then removed my gaff, and started stroking my clit.

"Why don't you lie down?" I asked him.

He lay down on the bed, his legs opened wide. I moved between his legs, and started kissing his shaft, starting at his balls. Inch by glorious inch, I kissed this monster cock, before reaching the head of it. My tongue slowly circled the head, enjoying the taste of it. This would be my first cock, as I put it in my mouth. I slowly started to suck it, using my tongue on the head. My hand started playing with his balls, while my other stroked him. I looked up and he was staring at me. His cock went deeper into my mouth, my saliva making him nice and juicy. I sucked him off, for a good fifteen minutes.

"Would you you let me fuck you, Maria?" he asked.

I wanted his cock so much, but had only used a dildo on my pussy. And it was much smaller than his big cock.

"I've never done it before Ross, but I want you so much."

"We'll take it slow Maria."

He told me to get on all fours. I did as he said, my ass in the air. He had brought some oil, and covered a couple of fingers with it. Slowly he inserted a finger into my pussy. It felt so good, as he slowly moved it, in and out.

"How does that feel?" he asked.

"It feels wonderful Ross."

He then inserted another finger inside me. Same again he slowly moved them in and out. My pussy was getting nice and wet now.

He put on a durex, and covered his cock in oil. Moving behind me, he slowly put the head of his cock inside me. It hurt and he pulled out straight away. He then used his tongue on my pussy, and my body started to shake. It was amazing, and I was feeling pretty wet.

"Relax Maria, we'll take it nice and slow."

I felt his cock enter me again, and it still hurt a little, but not as much.

"How does that feel babe."

"My pussy feels so tight."

While he was still inside me, he poured more oil on his cock, and went a little deeper. It felt unbelievable, and I heard myself asking for more. My ass went higher, my face buried in a pillow. Slowly he pushed deeper into my pussy. Inch by inch he went, until eventually he was fully in. I could feels his balls against my ass. I moaned in the pillow, asking him to fuck me. He started off slow, letting me feel all 9 inches sliding in and out. His hands were grabbing my ass, as he starting riding me faster. I wanted everything he had.

"Ross, fuck me harder," i screamed at him.

He started riding me fast and hard. I started matching his thrusts.

It wasn't long before we were both ready to cum. He pulled the rubber off, and we got into a 69 position. We both came at the same time, his cum dripping out of my mouth. We both stood up, and started kissing, our cum mixed together.

We lay in each others arms, both of us completely satisfied. He stayed the night, and as you can imagine, we fucked a lot more. My first date ended perfectly.