I hadn’t seen Mark for almost a year. His father had found a new job and subsequently his family had moved to another state. I’d known Mark since the beginning of high-school and I was really looking forward to seeing him again. We’d become friends since day one and it had come as quite a shock when he told me he was leaving. Not only had we seen each other in school each day, but we’d hung out together almost every day after school and at weekends too. We enjoyed many of the same pursuits such as jogging, tennis, swimming, board games, reading and such.
Mark was nineteen and would soon be starting college after taking a gap year during which he had been away travelling in Europe for a several months. I was a few months younger than Mark and was also taking a gap year, but unlike him I couldn’t afford to travel so I had been working odd jobs to make some savings for once I started college. I’d hardly heard from him since he’d gone away aside from a few brief emails but now he had invited me to stay for a few days and he seemed enthusiastic to see me again. I gleaned from his emails that while he was in Europe he’d enjoyed a lot of partying and had managed to pick up a few girls, so I was looking forward to hearing his stories. He had a way of spinning yarns such that he turned even the most banal situations into grandiose farces.
There was never a dull moment between us. We would make each other laugh with our silly antics and jokes, much in the same way as any two teenage boys would do. But, there was more to it than that. Something pulled us closer to each other than either of us would dare to admit, and even though both of us had clearly stated to one another that we were strictly heterosexual, on occasion I had felt strangely attracted to him and wondered if he felt that way too.
There had been an incident where we were messing around play-fighting and it turned into us almost kissing. I had pinned him to the ground and was lying on top of him. Both of us had been laughing until we were exhausted. As we lay there, our eyes caught in the same way as I had experienced with girls; that deep, dreamy look drawing me in. Just before our lips touched we both withdrew, embarrassed at what we were about to do. We avoided each other for several days after that and when we finally did meet up again, both of us kept quiet about what had happened before we gradually we slipped back into our old boyish ways.
That wasn’t the only time I’d felt attracted to Mark. Several times, I had found myself watching him and wondering, “what if?”, and then telling myself that it wasn’t normal. The fact was, no other guys affected me in that way and therefore I thought that I couldn’t possibly bisexual. Still, sometimes when we went swimming I couldn’t help but notice the bulge in his tight trunks, and when we showered I occasionally caught a quick peek at his circumcised cock. It made me wonder what it would be like to hold it in my hands and to touch it. I kept these thoughts strictly to myself.
Mark was of slight build, about 5ft7 tall, with light brown hair, light green eyes and full lips. He’d never been into athletics and for a large part he was excused from taking part in gym class due to having had asthma as a child. In true Mark style, he had taken advantage of this fact throughout his school years with the backing of excuse notes from his mom, despite the fact that he hadn’t had an asthma attack since he was about seven. He told me that he didn’t like being associated with the “boorish jocks”, and hastened to add that although I had to participate in sport, I wasn’t like the others.
When Mark jumped out of his car to greet me as I walked out of the railway station, I immediately saw that he had changed. His hair was now shoulder-length and wavy, and his face was tanned. He was wearing a black polo-neck sweater, tight blue jeans and pointy black shoes, a style I had never seen him wear before. He looked very smart, and when he smiled, I could see that he had whitened his teeth.
After a quick and slightly awkward hug, he ushered me into his sports car, an MG I think, and we drove away. During the ride, he told me that many things had changed since he’d moved, and that he’d learned a lot about life as an adult and especially about himself. I was intrigued, but he told me that he’d explain everything later.
“For now, let’s just enjoy the sunshine and the fields,” said Mark before revving the engine and accelerating.
He had a way of making life enjoyable. No sooner had he mentioned the sunshine and the fields then I felt happy riding alongside him in silence, watching the beautiful countryside whizzing past and feeling the warm wind blowing through my hair. I soon found myself grinning wildly and when I turned to look at him, he looked back at me, flashing his white teeth, his eyes beaming a smile like a madman.
“It’s great to see you again!” he shouted above the noise of the engine.
“It’s great to see you too!” I yelled back.
When we got to his house, I noticed that it was even larger than the one they’d had before. It looked more like a mansion or a small castle than a house, but I wasn’t complaining. Mark’s family had always lived to a high-standard of living. The good thing was that they never made a fuss about it. In fact, his family was more down-to-earth than a lot of people, wealthy or not.
“How’s your Dad’s job going? “ I asked.
“Quite well by the looks of it,” Mark replied, pointing at the house mockingly.
I realized that the timing of my question was rather obvious, and felt a bit stupid for having asked.
“I have no idea, really,” Mark added, seeing my embarrassment, “I hardly ever see him.”
He then went on to add that his older sister, Julia, was away at some week-long convention and that his Mom was visiting a relative and would only be back at the weekend, three days from then. He joked about how we could have a party and trash the house, but I knew it wasn’t his style. He said his Mom had prepared some frozen meals and that if we wanted anything different we’d have to fend for ourselves.
Mark pointed me to the guest bedroom and then took me on a tour of the house. It was truly magnificent, with high ceilings and large rooms. Downstairs there were two reception rooms, a living room, and dining room and a large kitchen. Upstairs there were five bedrooms, with two separate staircases leading up to them. Even my guest room had an en suite bathroom with a full sized bath and a shower unit. After the house tour, I took advantage of it and had a quick shower before changing clothes and returning downstairs to one of the reception rooms where Mark was waiting.
He offered me a drink, so I asked for a whisky and coke, which I sipped slowly as he told me about his adventures in Europe. For the most part, he had travelled by train and stopped off in several major cities all the way from Spain, up through France, the Netherlands and the Nordics, then back down through Germany, Switzerland and Austria to Italy. It sounded exhausting, but he assured me that he had also rested plenty and had time to think about his life. It was already the second time in the space of an hour that he’d mentioned changes and learning about himself.
“What is it that has changed?” I asked him.
“It’s not all that easy to explain,” Mark responded quietly, “and it’s something that you probably won’t understand.”
“Well maybe you should explain it, and then I can tell you if I understand or not,” I responded.
Mark sat back in his armchair, took a few deep breaths, and then told me his story.
“While I was in Spain, I met up with a couple of guys in a bar. They were curious about the US and asked me loads of questions about what it was like to live here and such, and in turn, I asked them a bunch of questions about Spain. We got to joking around and we were having a good time. At dinner time, they suggested I join them at a famous tapas bar, and from there we went on to a nightclub, only it wasn’t a normal nightclub. At first, everything seemed the same as I have seen in other nightclubs before the act gets going. There were regular couples and gay couples and lesbian couples, as well as a smattering of supposedly single people looking to connect.
When the act started was when things got strange. There were three beautiful girls on stage dressed in long silk dresses with slits up one side that showed off their legs as they danced to show music. I was mesmerized by how elegant they appeared and how feminine they acted. Of course, they were really transvestites.”
Mark paused at that moment, waiting to see if I would say anything.
“What happened next?” I said, not really knowing where this was going.
I suspected that he might say that he was turned on by one or more of the transvestites, but I didn’t want to jump to any conclusions. In fact I was feeling very curious, one might even say slightly titillated by his story.
“We sat down at one of the tables and watched the show for a while. The dances were all very professional, and the girls were just stunning. At around 11pm, one of the two guys I was with said that he had to leave, leaving me with just the one, called Juan.”
Mark stopped again, took a sip of his drink and asked me if I was ok with what he had said so far.
“Yes, I’m fine.” I answered almost impatiently, “Go on.”
“Well, by about midnight the girls were doing a striptease number, down to their underwear, and suddenly I felt Juan’s hand on my knee,” Mark continued.
“Holy cow!” I exclaimed, not sure if I should be shocked or not.
“The thing is, I didn’t mind.” Mark went on, “Are you shocked?”
“Not if you’re not,” I answered truthfully.
“Juan asked me if I was enjoying the show and admiring the beautiful girls. I told him that I was, and then he told me that he could introduce me to them after the show. Apparently he had been frequenting the club for years and he knew all the artists by name.”
“Did you take him up on the offer?” I asked.
“I did a little more than that,” Mark said solemnly, swallowing hard.
“Did you sleep with him?” I asked, thinking about Juan’s hand on Mark’s thigh.
“It’s a little more complicated than that,” whispered Mark.
“What then?” I asked quizzically. He really had my heart racing by then. I couldn’t think of a bigger revelation than Mark going to bed with a guy.
“We went backstage to the girl’s dressing rooms and Juan introduced me to them. They were really lovely and sweet, and spoke quite good English. At some point they started horsing around, saying I looked quite feminine and then they insisted that they be able to show me with ‘just a little makeup’. I let them go ahead, and one thing led to the next.”
My breathing was getting really heavy by this time. Mark’s story was fascinating, but more than that it had me excited. My cock had expanded and was fighting for freedom. I shifted into a more comfortable position before urging Mark to go on.
“Wow, that is some story!” I exclaimed, “Tell me more.”
“Are you sure you’re okzay?” said Mark.
“Yes, please go ahead,” I responded.
Mark continued his story.
“After the girls had finished with the makeup, they insisted that I try on some dresses. Juan was encouraging them all the while, insisting that I would look marvellous. They were such good sports and so nice, I didn’t feel intimidated at all. On the contrary, I felt like I was with old friends. One of the girls found a slinky high-neck black mini-dress, which Juan particularly liked. He took me by both hands and said I looked simply beautiful.
He then asked me if he could take me home. At first, I thought he meant that I would change back into my own clothes and that he would drive me home, but he then added that he would welcome a sexy girl like me at his place. I said yes, after which the girls found me some shoes and stockings, and a wig. One of them giggled and told me that Juan takes really good care of his girls.”
“So he took you back to his place?” I asked.
“Yes,” Mark answered, “It was something I wanted to do, and I’m happy that I did it.”
“He drove me to his home and treated me like a lady. He was very gentle and polite, never insisting on doing anything I didn’t like. He whispered beautiful words in my ear and made me feel very special. For once in my life I felt whole, as though a great weight had been lifted from me, setting me free. The next day when we said goodbye we knew we would never meet again, but we had both enjoyed a wonderful night together. ”
Mark leaned back in his chair and looked at me, as though waiting for more questions. I sat there watching him for a few moments, thinking about everything he’d said. I didn’t want to ask him for more details about his sexual encounter because that was between him and Juan, but I was curious about him getting dressed up like a girl.
“What was it like being dressed up like a girl?” I blurted out, not sure how to put it any other way.
“It wasn’t the first time.” Mark responded, “Which is partly why I went through with everything that night and why I’m happy I did. If I hadn’t done what I did that night, I still wouldn’t know what it’s like.”
“You wouldn’t know what it’s like dressing up as a girl?” I asked quizzically.
“No, I wouldn’t know what it’s like being treated like a girl.” Mark responded.
He went on.
“I have been dressing up in girl’s clothes since ages. It’s an integral part of who I am, not something I do just for fun or to have gay sex. I used to experiment with my mom’s and Julia’s clothes, but I started building my own collection after what happened in Spain. It made me realize that it’s something that I need and something that I want to pursue. I don’t want a sex change. I just want to be able to dress as a girl from time to time, to feel feminine and to be treated like a girl. I know this must all sound terribly weird to you, and I fully understand if you just want to leave.”
“Don’t be silly,” I said. “I’m very surprised by all this and I would never have guessed, but I don’t think less of you now that you’ve told me. In fact, I think it is fine.”
“You’re a real friend,” Mark said softly.
Later that evening after dinner, and after having thought through all that we had discussed in the afternoon, I decided that it was time for me to make my confession. If ever there was a time to come clean, it was then, right after Mark had poured his heart out to me.
“I have a story too.” I started, “It’s related to your story, but it’s also about you and me.”
Mark waited patiently while I related what I wanted to say.
“While you were telling me about what happened in Spain, I was thinking about you and what it all meant to you. Even though you say that you went ahead with everything willingly, you must have also been somewhat nervous.”
“I was,” Mark answered.
“I felt like I was right there with you, and I wanted to help you and to encourage you. I could tell how important it was to you to take those bold steps. I felt like I could see you through the eyes of Juan and I wanted to experience the beauty he saw in you, and I wished I had been able to tell you how much I cared about you. But, more than anything, I wished it was me holding you in my arms.”
“Really?” asked Mark.
“Only if you’d wanted it,” I responded
“Yes, I would very much like that,” Mark said quietly.
I noted that he said, “would” rather than “would have”, making my heart race for several minutes.
“I’m going upstairs now.” said Mark, “You should stop by and say goodnight to Carla. She’ll be there in about twenty minutes.”
I walked up the stairs in the dark and saw light coming from one of the bedrooms. The door was ajar, so I pushed it gently open. Carla was sitting on a chair by the window, in semi-darkness. She stood up and walked toward me. I could see she was wearing some sort of long robe as it glistened in the obscurity. When she came closer I could see her more clearly, and indeed, it was a silk full-length bathrobe. I took her by the hand and raised it to my lips to kiss it.
I didn’t recognize Carla as Mark or vice-versa, and even though I knew they were the same person, to me they were two distinct people. I was now in the presence of Carla, and she wanted my undivided loving attention. I could easily see why Juan had said she was beautiful, because she was. Her makeup had been applied exquisitely, and her lips looked fuller than ever, just waiting to be kissed.
She pulled me toward her and put her arms around my shoulder, I put my arms around her waist, and then we embraced passionately. The taste of her lipstick and the caress of her tongue made my cock as stiff as rock. I could feel it bulging against my pants and poking her in the groin area. Even in the darkness, I could see her eyes lit up like they had been on the day that we had nearly kissed. I pulled her tight and continued to taste her tongue with mine.
I slipped a hand inside her robe and put my hand behind her to caress her back. She felt silky smooth and her skin so soft. I rubbed my hand up and down, massaging her gently while we continued to kiss. I then slipped my hand further down her back until it reached her panties, and ran my hand over her buttocks. They were as round and deliciously soft and firm as any I had ever felt on any girl.
Carla tugged at the bottom of my t-shirt and lifted it up. We paused for a second while I pulled it over my head and off, and then she started running her fingers through my chest hair. I noticed that she had even taken the time to polish her nails red. She then started fumbling with the zipper on my pants, but I wanted to pleasure her more, so I pushed her hands away gently and fully opened her robe, which she let slide to the floor. She was wearing a black Basque, with matching panties, garter belt and stockings.
I was headed into territory I didn’t know, but I wanted to explore, much as Mark had wanted to explore that night in Spain. “If you don’t explore, you will never know,” I told myself.
I kissed her once again on the lips and then knelt down. I pressed my face against her panties and felt a stiff bulge through the nylon mesh material. I stayed like that for a moment, breathing heavily against her crotch, running my hands up and down her stocking legs and over her buttocks. She moaned lightly as I did this, and especially when I squeezed her butt cheeks tightly in my hand for a few seconds before releasing them.
I reached up and tugged lightly down on the front of her panties. Her she-cock popped out and I took it in my mouth, swirling my tongue around the head and delicately licking the rim. Simultaneously, I continued to caress her buttocks while she ran her hands through my hair, encouraging me in a soft voice to swallow her shaft completely. I obliged and sucked it down as far as I could and then retracted my mouth while dragging my lips over her throbbing member. I repeated this manoeuvre a few times while she shuddered in delight.
After a minute or so, Carla reached down and took me by the arms to pull me up again, then started undoing my pants. She reached into my underpants and pulled out my stiff cock, and then she knelt down as I had done and started to suck me off. I held her head in my hands, watching her beautiful reds lips engulfing my rod, leaving traces of lipstick as she sucked in my shaft and then released it. A couple of times she looked up at me to see if I was enjoying the attention.
“You can’t believe how good that feels!” I told her.
She pulled my pants down further so that I could step out of them. I kicked off my shoes, took off my underpants and socks, and followed her onto the bed. She pulled off her panties and lay on her back, her head on the pillow, while I knelt down facing her, pressing my groin against hers. I rubbed our shafts together, enjoying the feel of the two erect members pulsing with one another while I watched Carla relaxing and smiling at me.
“You look wonderful,” I told her.
“So do you,” she said.
She reached next to her, opened the top drawer of the bedside table and took out a tube of lube, which she then handed to me.
“Here, use this,” she told me.
I squirted some of the lube into my right hand, and then smeared it over our members before proceeding to masturbate the two of us at the same time. I loved the feeling of holding two shafts in one hand, the feeling of the oily lube as it slid softly over the rippling skin and the silky effect it had on my throbbing knob end. Judging by the engorgement of her she-cock and the look on her face, Carla was having a great time too.
“Come inside me,” she whispered.
I hesitated for a second, thinking to myself once again that this was all new to me, and wondering what it all meant. But, I had come so far and I didn’t want to turn back. I had started something and I had to carry it through. I had always relied on my logic to see myself through life, but this time I knew I just had to follow my heart for once.
Carla reached forward and took my cock in her hand, and proceeded to push the tip against her butt hole. She then took a bit of lube and smeared it both on the head of my cock and her hole.
“Rub it against me,” she urged, “It will open up.”
She lay back again while I stroked her hole gently with the tip of my cock. She smiled at me as I did so, and sure enough, after a couple of minutes I felt the entrance slowly opening up. I pushed back and forth gently until I was able to slide the entire head inside her.
“There, keep going!” she whispered.
I continued sliding in and out of her, going a bit deeper with each thrust until I was able to bury my shaft deep inside her. She pulled me close to her and started kissing me wildly, tears of joy streaming from her eyes. I pushed deep inside her and held myself there while we kissed. Her eyes were once again like deep pools of tenderness and loving.
“I want you so bad!” she cried, “Give it to me!”
I pumped her hard for minute, her butt hole now completely relaxed but still tight around my shaft. She lifted her legs and placed one over each of my shoulders. I then rubbed her stocking legs gently while gliding in and out of her delightful passage at a slower pace.
After a minute or two, I shifted aside and rolled her onto her stomach before pushing my cock between her butt cheeks and pounding her from behind. She moaned loudly as my thighs slapped against hers. The feeling of her soft skin and the sight of her biting into the pillow with pleasure as I pounded her made me cum explosively. I felt the hot sticky ejaculate spurting from my pulsating balls, streaming rapidly up through my shaft and shooting out of the tip to fill her awaiting ass.
I withdrew slowly and we rolled over to face each other.
“That was so good!” Carla said, tears still in her eyes.
“It was fantastic!” I replied.
We lay there kissing for a while, and then she rolled away from me, taking my arm and pulling it around her. We spooned until we feel asleep.
Later in the night, I awoke and was feeling horny again, only this time I wanted to make her come. Still spooning Carla, I reached between her legs and started fondling her she-cock until she became erect. I loved the feeling of her member in my hand, reflecting back on what I thought it would be like, and realizing that I had wanted it more than I really knew.
I rubbed the head softly and traced my fingers around the rim. Then, I took the whole shaft in my hand and felt the soft ridges rippling while sliding my hand up and down to pleasure her. She moaned as I did this, telling me that I didn’t have to. I told her that I wanted to, and proceeded to stroke her until she came into my hand.
“You are the best!” she whispered.
“No you are the best!” I replied softly.
I held her tightly, exhausted but contented, happy that we were together again, even if only for a while. We fell back to sleep.
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<a href="https://www.lushstories.com/stories/crossdressing/meeting-carla.aspx">Meeting Carla</a>