After a morning of shopping, I went for a hamburger. As I sat there with my bag of goodies by my side, a man in his early thirties sat down at the table next to me. He beamed a smile at me and said hello. It was unusual for people in the city to be friendly to strangers, but then again, he didn’t look like a man from the city. He must have been in his mid-thirties. His face was rugged, and his hair was unkempt. His clothing was clean, but it looked worn. I guess he must have been a manual labourer of some kind, perhaps a farmer. His hands confirmed my theory; they looked rough and strong. I smiled back briefly and said hello in return before turning my attention back to my meal.

I was nineteen at the time, very much unaware of the world of cross-dressing. All I knew was that I had always had a penchant for dressing up in girly clothes in private. My shopping spree that morning had consisted of visiting several stores on the city’s main strip looking for items to fill my female wardrobe. Since I left home just a few months previously, I finally had the freedom to dress up as much as wanted in the secrecy of my own apartment. With some extra cash from my new job, I was really going wild with my purchases. That morning, I had splashed out on several undergarments, a couple of skimpy dresses, a skirt and blouse, and a pair of classic black high-heels. I was looking forward to wearing them at home and basking in the girliness while watching some DVDs.

“Nice catch,” said the guy next to me, “I’m Nash.”

He held out his hand as he introduced himself. I had no idea what he was talking about, thinking it must have been a reflection on a sports event. I reciprocated and shook his hand. His grip was surprisingly soft, despite the roughness of his skin and the thickness of his fingers. He seemed to show a genuine interest in meeting me.

“Hi, I’m Remy,” I said in return, “I’m not sure what you mean. Can I help you with something?”

“I meant your shopping,” he chuckled and winked at me, “That’s some lucky girl.”

I felt very small suddenly, as though I had been caught with my hand in the cookie jar. I didn’t know what to say at first. I looked at him for a second, noticing his swimming pool blue eyes and bright smile. His teeth were immaculate for an otherwise scruffy-looking guy. In fact, there was something very charming, sexually attractive about him. I quickly brushed that thought aside. I wasn’t typically attracted to men and had certainly never entertained the thought of having sex with one. Besides, he was a stranger and who knew what he was looking for.

“Have you been following me?” I asked.

“Not exactly,” he replied, “I just saw you in the store across the street. I thought it was cute how you were holding up the lingerie. You must have a passion for it. It was quite fascinating.”

“What’s it to you?” I said quite abruptly, even rudely.

I was thinking of getting up and storming out of the restaurant. This guy had been stalking me and was making comments that made me feel embarrassed.

“Woah, it’s ok!” he said, seeing my discomfort, “I didn’t mean to spook you. I kinda have an interest in that sort of thing. I mean, you look like an intelligent guy. You must know that some guys like to, well, dress differently. I’m not saying that you were buying that stuff for yourself, but if you were, it’s totally ok with me. I’m not a person to judge. In fact, I would think it was awesome if you were. As I said, I’m simply interested.”

“What kind of interest?” I asked, still hesitating if I should run away or not.

“Listen, Remy,” he said softly, “I’m not saying that the clothing is for you, but if it is, I have known a few guys who go home and dress up on their own. It’s a very lonely life, especially as you get older. You end up with a wardrobe full of beautiful feminine clothes and nowhere to go, or you get married and hide your secret forever. It’s better to have a few friends who understand you, who encourage you, and who can help you in times of need. I have some friends who cross-dress, and I admire them for their courage and their beauty. I’m sorry if I have upset you.”

The way he delivered his message somewhat reassured me that he had a genuine concern. The look on his face was asking me for understanding and forgiveness.

“I’m sorry,” I said, “I’m not used to talking to complete strangers.”

“Well, then let’s not be strangers,” he replied, “Why don’t you come back to my place for a drink and we can chat some more. I live just around the corner.”

I hadn’t confirmed that I had been shopping for myself, but I figured that it was obvious to Nash by now. I hadn’t refuted the claim, and he was quite clear in his assessment of the situation. In the back of my mind, I knew that if I went with him, some sexual activity would probably occur. In fact, my cock was twitching slightly at the thought, even though I was somewhat conflicted at engaging with a man.

“OK,” I said meekly, “Just for an hour or two. I need to be home by 3 pm.”

I said 3 pm because I wanted to time-box the meeting to give him the impression that I wasn’t going to hang around all afternoon. I also wanted a deadline in case I felt I needed to escape.

“That’s fine,” he replied, “I have some things to do later this afternoon too.”

---

His apartment was quite small but tidy and quite well-decorated for what I thought was a bachelor’s pad. He saw me looking around and swiftly explained that he and his wife had separated a couple of years previously. I sat down on the couch while Nash went to fix a drink for both of us.

At first, we chatted about mundane stuff like where we were from, what we did in life and where we worked. Nash was indeed from the country, but he had moved to the city and was now in the construction business. As I sat there listening to him, he was interesting, but I could feel something missing in why he had asked me to come back to his place, and there it was.

“Why don’t you slip into something more comfortable?” he said with a wry smile.

My cock shot up immediately. The moment was then. He was asking me to model my new clothes, and I wanted to show him. It would be the first time ever I had dressed up as a girl in front of another person. I felt so nervous and excited at the same time.

“You can use the bathroom,” he said, “There’s still some old makeup my ex left behind.”

---

I took my time in the bathroom. I wanted to get everything right. I picked out a matching red cotton panty and bra, black stockings and suspender belt, the red silk dress and the black heels. My head was rushing with thoughts about what I was doing and what might happen, but I was caught up in the moment of excitement. I had never felt so exhilarated in my life.

I opened the wall cabinet and found the makeup. There was quite a selection. I applied a bit of foundation and mascara, eyeshadow and finally a deep red lipstick that matched perfectly with my dress. I brushed my hair into a pageboy style and held it into place with a pretty white bow hair clip. When I looked at myself in the mirror, I felt quite proud of my achievement. The girl looking back at me was who I wanted to be.

---

“Wow, you look amazing,” said Nash.

“I’m sorry it took so long,” I replied.

“Come and sit next to me,” he continued, patting the space on the couch.

I teetered over to the couch and sat down. I wasn’t used to walking in heels, but it didn’t seem to bother him. He just smiled from ear to ear, obviously enjoying the moment.

“How do you feel now, my dear?” he asked.

“I feel a bit shy but good,” I answered, “I’ve never done this before.”

“There’s nothing to worry about,” he continued, “There’s a first for everything. Just relax.”

While saying this, he placed his hand gently on my knee. The touch of his strong hand through the delicate nylon material of my stocking caused my cock to swell further than it already was. I felt a dribble of precum oozing from the tip of my shaft.

“You don’t mind, do you?” he asked, nodding at his hand on my knee.

“No,” I replied quietly, “It feels nice.”

“See, this is what I was talking about earlier,” he said, “You could go home and try on some clothes, perhaps twirl around a few times in front of the mirror, read a book or watch some television, maybe masturbate, but then you would be on your own. You do masturbate, I assume?”

“Yes, sometimes,” I replied, my face blushing bright red.

“Good!” he continued, “It gets rid of the tension.”

He gently rubbed his hand up and down my leg toward the top of my thighs, sliding my dress slightly toward me. The feeling of his hand rubbing me that way was ecstasy. I felt more drops of precum dripping from my tip.

“You know,” Nash said, “Seana and I used to help each other like that. Whenever one of us was stressed, we would tug each other off. You know, nothing gay about it. It was just a game we played to distract ourselves from the bigger problems in life.”

“Who is Seana?” I asked.

“She’s a girl I used to know in college. A pretty girl like you, but not as pretty as you. When she left college, she got married, and I never heard from her again. I still miss her and the fun we used to have.”

“I’m sorry to hear that,” I said, feeling Nash’s hand slide up above my stockings and on to my bare thighs. I felt like I was about to cum.

“What are you thinking?” he asked.

“Nothing in particular,” I answered, “I’m just listening to you.”

The truth was, I couldn’t really think much. His voice and his touch had mesmerised me. I wanted more.

---

His hand finally reached my crotch, and he started to stroke my cock through my panties. He put one arm around me and pulled me tight, giving me a kiss on my neck while he grasped my shaft with his free hand. I felt very vulnerable, but safe in his arms at the same time. He fumbled around in my panties, releasing my shaft and playing with it gently, stroking it up and down. His hands gripped tightly around my throbbing dick, the callouses on his rough hands reminding me of what a manly man he was. The way handled me, I felt like a girl, and I just wanted him to show me the way.

The next thing I knew, he had leaned over and pulled my dress up to my waist and plunged his head right down, engulfing my dick in his mouth. I almost spunked right in him while he sucked me off. The feeling of his tongue swirling around my shaft while he bobbed up and down, the licking and sucking felt totally awesome. He tickled my balls with one hand while rubbing my breast area with the other. I felt like I was in heaven with all that attention. After a minute or two, I had to stop him because I wanted to return the favour.

I started fondling his cock through his pants. He was hard, and from what I could feel, big too. I tugged at his zipper and then undid his belt buckle before pulling his underpants down a bit and releasing his shaft. His cock sprung out at me like a jack-in-the-box. Even though I’d never seen another man’s cock that close up before, it looked beautiful. I licked the tip a few times and then took a mouthful. It was much bigger and wider than I had expected, but I managed to work back and forth until I reached his balls slowly. I almost gagged as he thrust himself deep into my throat.

I slipped my hand inside his shirt and felt the hair on his chest. It was warm and inviting. I felt like I could snuggle up with him at night. He made me feel wanted and I wanted him too, even though we had just met. It was at that point that I first realised that all I really wanted to be was a girl with a man to love me and take care of me. I was more than just a cross-dresser.

“Oh beautiful,” he moaned, “You’re such a good girl.”

I started crying. The emotions were just too much for me. I sat up again, sobbing.

“It’s ok my dear,” Nash said, “Let’s take it slowly, ok?”

“I’m sorry,” I replied, “It’s just so overwhelming.”

I sat there for a minute or two, getting my emotional self together, while Nash held me softly with one arm.

---

He stood up and took my hand, helping me stand up off the couch. He put his arms around me and pulled me close to him. I felt good in his arms. He nuzzled his head into my neck and kissed me softly. His closeness was like something I had never felt all my life.

“Are you ok now?” he asked, “We can stop if you like.”

“Please don’t stop,” I whispered.

He rubbed my back a few times and then lifted the back of my dress, grabbing my buttocks in his hands. I loved the feel of his hands holding me through the material of the soft cotton panties. I wanted him to carry me to bed.

He unzipped my dress from the back, and let it fall to the floor. I was standing there in only high-heels and lingerie.

“Beautiful!” he exclaimed, kneeling to suck me off again.

Once again, he took pleasure in gulping down my shaft and sliding his tongue over my throbbing veins. I cannot explain how much pleasure I felt standing there, dressed up as a girl and having someone pay so much attention to me. His words from earlier resonated with me. I could have gone home for a wank, but this was so much better.

Nash stood up and removed his shirt, shoes and pants, then pulled me close again, this time tugging the back of my panties down and sliding his fingers up and down my ass crack. I knew what was coming and sure enough, he soon slipped a finger inside me.

“I want you, baby,” he whispered.

“You can have me,” I replied.

He instructed me to lean over the coffee table and spread my legs. Soon, I felt him rimming my asshole with his tongue. At first, it was a bit ticklish, but then I felt my cock swelling hugely, especially when he grabbed my shaft in one hand and swallowed my balls. He played with them in his mouth, swirling them around like a toy. He then resumed licking my ass, darting his tongue in and out of my hole while I clung on to the far edge of the coffee table.

I was just thinking it couldn’t get any better when I felt the tip of his thick shaft poking into me. With all the licking he had done, my ass was already loosened up, and it only took a few pushes before the tip of his cock was inside me. He grabbed me around the waist as he moved back and forth, each time going a little deeper. By this time, I was almost breathless but very happy.

Finally, Nash was fully inside, thrusting back and forth with increasing motion.

“Fuck me deep!” I squealed.

He grabbed my ass cheeks as he increased the rhythm, holding on so tightly that it almost hurt. I didn’t care. I wanted his semen inside me.

“Cum, please cum!” I screamed, my cock dripping, ready to explode.

In just a few more thrusts, I heard Nash groan and felt the warmth of his thick, sticky cum spurting inside me. It was my initiation to anal sex, and I couldn’t think of a nicer guy to teach me.

With his cock still hard in my ass, he reached around and took my knob in his hands. It only took a few gentle strokes before I spurted violently all over the floor, while he clung tightly to my waist.

It was all over, but what a ride!

---

As I walked back home that afternoon, I felt full of joy, knowing that I would be seeing Nash again.