It was my year off school, and I had decided to spend it far away from my family, far away from friends, and find myself. Having grown up in the inner city, there was no better place for me to reflect upon life than in this mountain wilderness. I was used to life being constantly busy, my parents pushing me into hard work at school and hard play outside of school, as well as all the extra-curricular activities including sports, theatre, music and dance. For now, I felt safely tucked away from the bustle of everyday life, and had spent most of my time reading books and lounging around, thinking about what I wanted out of life.
My host family didn’t complain about my lack of physical activity. They were an older couple who had never had any children and they were quite happy to have a surrogate son staying with them. They treated me very well. Mrs. Foster was happy to cook and clean for the family every day while Mr. Foster, now retired, sat around reading his newspaper and smoking his pipe. I sat all day long on the sofa devouring novels I had brought over from Europe. We made quite the old-fashioned family in many ways, but I knew it couldn’t last forever.
Today was Christmas day. Mrs. Foster had invited a couple to dinner that she and Mr. Foster had known for many years, and a friend that they called Uncle Joe. Joe wasn’t really an uncle, at least not to them. He was Mrs. Foster’s sister’s boyfriend, although many years younger than her, and he had been coming to Christmas dinner for the last eight or nine years since Mrs. Foster’s sister, Mary, had died in a tragic accident on a ski lift.
I had met Joe once before while we were touring the region. He lived in an isolated cabin on the side of a nearby mountain. We had stopped at his place for a couple of hours for refreshments and he had asked me loads of questions about my upbringing, my travels, why I was in Canada, what I wanted out of life, and so forth. He seemed very inquisitive, but at the same time quite genuine. Still, I felt a little uneasy because I felt like I was exposing my entire life to a stranger and yet knew little about him. He had a knack for keeping the conversation focused on me and my life, without offering much information about himself. I had made a mental note to learn how to ask questions instead of just answering them, realizing that I was young and inexperienced in the art of conversation.
—
When I entered the house Mrs. Foster informed me that their three guests had already arrived. I apologized for having been so long, but she waived away my apology and told me to go into the living room and say hello. I hadn’t yet met the Greens, and as I shook their hands I realized that they were about the same age as the Fosters. Mr. Green looked like a retired Colonel, whereas Mrs. Green looked like a typical housewife, in many ways similar to Mrs. Foster.
Upon seeing me, Joe stood up and leaned toward me with a big smile on his face. I was about to hold out my hand when he put his arms around me and gave me a big hug, his arms wrapped tightly around my back and his cheek next to mine. I was taken aback and started to go bright red in the face. I wasn’t used to this kind of behavior between men, especially after I had only met him briefly once before.
Mrs. Foster laughed happily when she saw my reaction, and said “Well, Joe sure is happy to see you!”
“I sure am!” said Joe, a smile beaming from ear to ear.
“Let’s sit down and have a little drink before we start on dinner”, Mrs. Foster continued.
We sat there drinking our glasses of sparkling white wine, nibbling hors-d’oeuvres, and making small talk about the weather until this lead to Mrs. Foster and Mrs. Green breaking off into their own conversation about domestic issues, while Mr. Foster and Mr. Green spoke about hunting in the old days. That left Uncle Joe and me to strike up conversation together. This time, I managed to learn that Joe was from the city, like me, but had come to the mountains after he met Mrs. Foster’s sister, Mary. He had worked for a few years in advertising, but didn’t really need the money as he was independently wealthy from his family. After Mary had died, he decided to stay in the mountains because he felt happier being close to her origins, and denied the “life of ugly riches” as he called it. He explained that even though he was well off, he had decided to live out his days humbly in his two room cabin. I was quite impressed by his story.
After a while, Mrs. Foster stood up an announced that it was time to exchange gifts. She went to the tree and started to rummage through the boxes, finding one gift for each of us and handing it to us while announcing who it was from. We had all been asked to purchase a small gift for each other as a token of gratitude for the season, and luckily Mrs. Foster had advised me to purchase socks for Mr. Foster, a scarf for Mrs. Foster, and a tie for Uncle Joe. She had even helped me choose them from the only department store in a nearby town.
My first present was a Canadian shirt from Mr. and Mrs. Green, as a souvenir. I smiled and thanked them, while Mrs. Foster handed me a second gift, this time from Uncle Joe. I lifted the flaps on the wrapping paper surrounding the oblong box, thinking it was probably another shirt. The box shape was not unlike the one I just had received from Mr. and Mrs. Green. After removing the paper, I lifted the lid off the box and saw a pink silk lingerie-looking item with lacy ruffles inside. I quickly closed the lid and looked at Uncle Joe.
“Do you like it?” Joe smiled.
“I’m not sure”, I blurted, “If it’s for me.” I said. I was blushing bright red again.
Part of the embarrassment was due the fact that I had just been given an obviously feminine and very intimate gift from another man, and part of it was due to the fact that I liked the idea, but didn’t want to like it. As a child, I had often secretly worn my sister’s clothing, but it had never occurred to me that my penchant would be known by anyone else. I had never told anyone about it, and had never been caught. Somehow, the thought that Uncle Joe may have been aware of my inner desire to wear female clothing was exciting and damned scary at the same time. I reasoned that he had probably made an innocent mistake, though at the same time I wanted to keep the gift. On the other hand, I wondered if he was provoking me, either to engage in sex with him or perhaps as a joke to test my manhood. Before I could clear my mind of all these conflicting ideas, Mrs. Foster saw that I was disturbed by the present from Uncle Joe.
“What’s the matter, dear?” she said to me, looking concerned.
“Nothing”, I responded abruptly, trying to buy some time. I placed the closed box beside the armchair.
Joe sat there nonchalantly with a smile on his face, looking pleased despite the commotion.
“What did you get from Uncle Joe?” continued Mrs. Foster.
I hesitated for a few moments, and then decided it was better to come clean with the situation.
“I think it’s a mistake”, I said, swallowing hard. “It’s some kind of ladies lingerie.”
“What on earth?” exclaimed Mrs. Foster, turning to Uncle Joe with a puzzled look on her face.
Uncle Joe sat bolt upright on his chair, leaned forward, and put his right hand up to his forehead, looking somewhat surprised.
“I’m terribly sorry”, he said, “I must have mixed up the boxes. That was supposed to be for my sweetheart.”
Everybody laughed at what had just happened, whereas I felt confused. On the one hand, I was relieved that Uncle Joe hadn’t deliberately given me the lingerie, but on the other I was sad that I would have to give it back. I had already formed thoughts about wearing it in my room later that evening. It had been a long time since I’d enjoyed that delicate feeling of being feminine.
“Good God, man”, exclaimed Mr. Green to Uncle Joe, “He’s not a Sissy boy you know.”
“Indeed, not one of those transvestite types you see on television these days”, Mr. Foster guffawed.
“Stop it.”, said Mrs. Green, “He’s a very sweet boy.”
“Yes, but not that sweet” said Mrs. Foster, winking at me.
They all enjoyed the merriment at my expense while I sat there blushing profusely, trying to smile.
“I’ll tell you what”, interrupted Uncle Joe. “If you come down to my cabin on Tuesday, I’ll give you your real present. “Here, give me that box,” he continued, extending his hand toward me in a gesture for me to return the gift. “I’ll make us supper and we can have a drink to this unfortunate mistake.”
I thanked Uncle Joe for his offer and agreed to meet him at his cabin on Tuesday at 6pm.
—
The rest of the evening went smoothly, with no further incidents. That is, until Uncle Joe – who was sitting beside me – put his right hand firmly on my left knee after the coffee, and reminded me that he was looking forward to seeing me again the following Tuesday. Once again, it seemed innocent enough, but it sent a strange sensation through me. His demeanor was gentle and kind, giving no sense of anything untoward, but the touch of his fingers as he squeezed my knee felt sensual, sexual even. We had hardly spoken throughout the meal, listening instead to the Foster’s and Green’s stories of times gone by.
I felt intimidated by the evening’s earlier incident, and just wanted to lie low until the evening was over. Joe finally let go of my knee before declaring that he needed to run to get ready to make some repairs on his cabin the following morning.
—
On Tuesday afternoon, I took the bus to Uncle Joe’s. It was a straight run from the Foster’s house, just a few miles down the road. As I made my way to his place, I felt excited and worried about what might happen. I still didn’t know if he was trying to make a pass at me or whether it was just genuine friendliness. In fact, I wasn’t sure how I would feel if he did make a pass at me. I had never been attracted to a man before, and wouldn’t have known how to behave if I was. I certainly wasn’t going to press the issue with him, although I did awkwardly enjoy his strange attention. I reminded myself that he had been Mary’s boyfriend and was therefore unlikely to be gay. “Besides” I thought, “It’s OK to enjoy the attention, so long as it doesn’t get out of hand. But, what is getting out of hand?”
Before I could finish all my strange and wonderful scary thoughts, I had arrived at Joe’s cabin. I knocked on the door and he came out almost immediately.
“Come in, come in”, Joe said, with his usual big smile.
As I walked through the doorway, he put his arm around my shoulder for a second, and then proceeded to remove my coat while I lowered my arms to let him pull it away from me. I realized at this moment that he was behaving as if I were a girl, and I was also behaving as though I were a girl. “No man remove’s another man’s coat in this way” I thought, “And yet it feels so natural.”
“Welcome to the mansion”, he said, laughing at his own joke. “Take a seat on the sofa over there. I’ll be back in a minute. I’m making stew. I hope you like stew?”
“Yes, very much”, I said, making my way toward the sofa.
Joe hadn’t gone very far. In fact, he ‘d just stepped over to corner of the same room, stirring a pot on the stove range. The last time I had been here, I didn’t really notice the place because I was too engrossed in conversation. Now, I looked around, observing that aside from the sofa and kitchen table with two chairs, there was no other furniture in the room. The floor was covered with a couple of thick woolen rugs, which gave a feeling of coziness to the place, but it certainly was a far cry from typical city life, or even most mountain life for that matter. The Foster’s place was at least ten times the size of Joe’s cabin. Still, it was a warm and comfortable place, I thought.
I looked at the door to my right, which was closed. I assumed it must be the bedroom.
“That’s the bedroom” said Joe as he walked back toward the sofa. “Hang on a second. Before I forget, I’ll get you your present.”
Joe disappeared into the bedroom and emerged a few seconds later with a square gift-wrapped box in his hands. He sat down on the sofa next to me and handed the box to me with both hands, as though making an offering to the gods.
“This time I hope you will like it”, he said.
I tore off the top of the wrapping, and pulled it aside to reveal the lid of the box. Hesitantly, I lifted the lid, under which there was a layer of crimpled white tissue. I looked at Joe for a second and he smiled at me.
“Go on!” he said, “It doesn’t bite.”
I took out a wad of the tissue and saw more tissue underneath. Then I took out a couple more pieces and stared into the box, in which I could now clearly see the same silky pink material as I had at the Foster’s house. My heart leapt at this discovery and then suddenly I felt very shaky.
I looked gingerly at Joe, who was still smiling, and said to him “It’s the same thing.”
“Yes, but this time I hope will you like it.” he repeated.
“But, I’m a guy”, I started to exclaim. “I can’t wear this…”
Before I could complete my protest, Joe leaned forward and put his index finger over my lips in a shushing motion, and said “You can wear it if you want to. Nobody can stop you from wearing what you like. Guys clothes, girls clothes, they’re all just clothes. Besides, if it makes you feel good then you shouldn’t feel bad about it.”
I was red in the face once again, and didn’t know what to say. I just sat there with my head held down for a couple of minutes, wondering how Joe could have known my secret, and what his intentions were by giving me such a gift. I figured that he would probably want to see me wearing it, and maybe even want to have sex with me while I was wearing it. I felt scared.
“Aren’t you going to look at it?” Joe asked.
I didn’t answer his question directly, but proceeded to pull the silky item out of its box.
“It’s beautiful”, I said shyly. “Thank you.” I could hardly believe that I was thanking another man for giving me lingerie, but it was happening and it was real. It felt surreal, but it was real. It felt weird and strange and wonderful and scary all at the same time.
“There’s a little something more in the box”, said Joe.
I reached into the box and pulled out a pair of pink stretch-nylon full back panties, decorated with the same light pink ruffles as the negligee, and as suspected, under the next later of tissue there was a matching bra.
“I don’t know what to say”, I said.
Joe laughed gently and told me that the look on my face was enough to let him know that I was happy. He put his arm gently around my waist and squeezed me toward him while burying his face into my neck. After a few seconds, he let go of me, and sat back on the sofa.
“Go try them on”, he said, “I wouldn’t want them to be the wrong size. If they don’t fit I can always send them back to France and order new ones.”
“Oh my God”, I thought, “France. They must have cost a fortune.”
I still had no idea what exactly Joe wanted, nor how he knew that I enjoyed crossdressing. Maybe he had clued in and was trying to help me out. Maybe I was just being naïve, and he wanted something further from me. I didn’t know what to think any more, but I decided to go with the flow until it felt too uncomfortable.
Joe ushered me into the bedroom and told me to take my time, closing the door behind me while he stayed in the living area. The bedroom was equipped with a double bed, and had fitted wardrobes along both walls. There was a window above the bed with a view to the mountains beyond. It was getting dark, but I could still faintly see the snow caps in the distance.
I gingerly stepped out of my clothes, pulled on the panties, strapped on the bra, pulled the negligee over my head, inserted my arms, and smoothed it over my hips. The routine of dressing was familiar to me, except that I had never worn female clothing in a stranger’s house.
The negligee was quite short, so it only just covered the top of the panties. I looked at myself in the full-length mirror, seeing the familiar image of me as I wished I could be every day. I swirled around while watching my ruffled butt in those form-fitting panties. The bra cups were small and padded in such a way that they lifted my chest to form little breasts. Everything fitted perfectly!
I walked past the mirror a couple more times when Joe called from behind the door.
“How’s it going in there?” he called.
“Fine”, I called back. “It’s perfect, thank you.”
“You’re welcome. There’s some old makeup in the top drawer of the dresser, if you like.” Joe continued.
I hesitated to answer for a second. I had never done makeup before, and I reminded myself that I would have to go back to the Foster’s house later that evening. “What if I can’t remove it properly?” I thought. Besides, I really wasn’t sure I wanted to try makeup for the first time at Joe’s place, nor wanted him to see me wearing makeup. I wasn’t even sure I wanted him to see me in lingerie, for that matter. “What if he rapes me, and then kills me?” I thought for a split second, then rationalized that he had been married to Mrs. Foster’s sister for a few years, and was still a good friend of the family after several more.
“Thanks, but I’ll pass on the makeup.” I called back.
“As you wish,” Joe replied, “It makes all the difference.”
A few minutes later, and after hearing no further comments from Joe, I was about to get changed back into my male clothes. I figured that seeing as there was no request from him to actually see me wearing the lingerie, it would be appropriate to get dressed before returning to the living area. Then, I heard a knock at the bedroom door.
“Can I come in now?” he asked loudly but gently.
I gasped aloud and said “I’m still dressed up.”
“Well I sure hope so.”, Joe responded, and before I could make any further objections, the door opened and I saw a woman standing before me, dressed in lacy black lingerie from head to toe. She was wearing black high heels. Her shiny black hair was cut in a sleek bob, and her face was made up with long black eyelashes and deep rouge lipstick. It took me a couple of seconds to realize that is was Uncle Joe.
“You’re not the only one.” he said, smiling, except that this time he looked beautiful rather than handsome. “There are many of us in the world. As you grow older, you’ll learn to recognize them, and hopefully meet them. They’re mostly very nice people, in search of many of the same things as everyone else; freedom, love and happiness.”
I felt calmer all of a sudden, knowing that Uncle Joe shared my secret.
“Let’s get you some makeup”, said Joe, “And by the way, my name is Josie for this evening. What’s yours?”
“I don’t know” I responded “I’ve never had a girl’s name.”
Josie looked at me for a moment, and then said “Emily. You look like an Emily.”
I sat down on the edge of the bed and thought about my new name while Josie rummaged around in the dresser for the makeup. I liked Josie’s choice of name. It sounded very girly, which was exactly how I felt when I wasn’t trying to act like a guy. It could have been a name I’d choose for myself, but now it had been chosen for me. So, Emily it was.
“Sit still, for goodness sakes!” said Josie as she tried to apply the mascara to my eyelids.
“I’m sorry.” I said, “I’m not used to this.”
“You’ll get used to it.” Josie responded. “With a bit of practice you’ll be able to put on your makeup in under two minutes.”
“If I get used to it.” I answered.
“You will for sure”, Josie continued. “You’re a natural. Such a beautiful looking young lady. You’re very pretty, you know.”
This last comment made me excited. I felt a twitch in my panties as I thought of myself being called pretty. I adjusted my legs to prevent my penis from popping up into view. But, Josie immediately noticed what I was doing and made a comment.
“Don’t worry about that.” She said, “The old pecker can’t help it. It comes with the territory of being male and female at the same time.”
I blushed profusely while Josie made the finishing touches to my makeup, applying a dark pink lipstick with a touch of lip gloss.
“There you go.” She said. “Look in the mirror and tell me what you think.”
I stood up and turned toward the full-length mirror. What I saw wasn’t me, or rather it was me, but it was me as the girl I remembered from when I was young. It was me as the little girl with the big eyes and a fair complexion, all grown up into a woman. I recognized myself as I had imagined I would become, before I realized that I would never be a girl despite my childhood dreams and wishes. It was so emotional seeing me as that woman that I almost started to cry.
Josie put her arm around me and pulled me gently toward the living area. As I walked toward the sofa, she popped back into the bedroom, emerging with a pair of patent leather pink high heels. She told me to try them on, which I did. They were slightly too large, but not enough to make me fall over while walking. Although I hadn’t worn heels for many years, I had a lot of practice at home until my feet outgrew those of my sister and mother. I made a few test steps up and down the room, to which Josie nodded with approval.
“Let’s eat now.” Josie said.
We sat down to the stew and vegetables. It was delicious. I concluded that Josie had not only accomplished a great look as a woman, but also knew how to cook. I suspected that she could probably do just about anything that any other real woman could do, and told her so.
“I try my best.” she said modestly.
Josie asked me a few questions about my past crossdressing, where I started and what I did, and I made sure I reciprocated with the same questions toward her. Both of us had started as young children, and both of us had tried on our sister’s clothes. Josie explained that it was often the way. Most crossdressers started young by either borrowing their sister’s or their mother’s or their aunt’s clothes. “Wherever the opportunity arises.” She said.
After dinner, we cleared the table and went to sit on the sofa. I was about to ask Josie if she knew a lot of crossdressers when she asked me a question instead.
“I guess that you must have masturbated while wearing your sister’s panties?” she asked. It was actually more a statement of fact rather than a question.
I blushed and said “Yes” in a quiet whisper.
Josie turned toward me and ran her hand up my leg in a sweeping motion. It reminded me of her taking my knee at the Foster’s, only this time we were both dressed in lingerie, and the feel of her hand on my bare thigh was electrifying. I could feel a rush of blood swelling into my penis.
“It’s perfectly normal.” Josie stated in a matter-of-fact manner. “We’re all sexual beings with different turn-ons and turn-offs. Panties can have quite a powerful effect on a young man, whether you’re a crossdresser or not. The main difference is that crossdressers also like to wear them, as well as many other female items, of course.”
I looked at Josie to see if had more to say, but she just sat there next to me, seemingly mesmerized while she stroked her hand gently up and down my thighs and over my knees. The effect was causing my penis to swell almost to the point of discomfort. I tried to think of anything except her touching my leg, and I didn’t want to be rude by pushing her away.
She pulled gently at my left leg to separate it from the right one, whispering “Just let it happen if you like it. Don’t try to fight your emotions with logic.”
I let her pull my legs apart and closed my eyes. My penis sprung erect and was pushing hard against the fabric of the panties as she continued to run her fingers over my bare legs, teasing me. My mind was racing and my heart was beating rapidly. I reminded myself once again that I could stop at any time, but I was really enjoying the moment, and Uncle Joe was in fact Josie, not just a man as I had thought.
As I sat back on the sofa, Josie started to alternate between tickling my thighs and tracing her fingers over my erect penis. I thought I was about to explode as I felt her gentle touch just beyond the fabric of the panties. She started running her thumb and forefinger up and down my shaft, squeezing the head in a rhythmic motion. My former girlfriends had never had such an effect on me. It was a fantastic sensation.
I opened my eyes briefly, and Josie shifted from the couch to kneel in front of me. I knew she was about to give me a blowjob, and all prior thoughts of stopping were now gone. Not only was I going to let her give me that blowjob, but I desperately wanted to feel her beautiful red lips around my swollen cock.
Josie leaned forward, put her arms around my waist, and pulled my lower half toward the front of the couch. Then she popped my penis out of the top of my panties and lowered her head into my lap. Her tongue made swirling motions around the head of my cock, and occasionally she dropped down to swallow the top half of my shaft, holding her mouth closed tightly enough that I could feel the softness of her lips as they slid like silk over my swollen member. After a couple of minutes, she sat slightly further back and pulled my penis toward so that I could watch her more easily as she swallowed the whole thing.
She gazed up at me as she sucked, looking me straight in the eyes. I loved the way she had done her makeup. The eye-shadow, eyeliner and mascara made her eyes look bigger and brighter, in just the same way as she had done with mine. She was wearing a perfect level of toner and rouge, but it was really her lips that made all the difference. The deep red color gliding over my cock was enough to drive anyone mad, and even when she wasn’t sucking me I had noticed how full and pouty they seemed. As Uncle Joe, I hadn’t seen this, but now that Josie was here it was evident.
She stopped swallowing me and started to lick my balls, scooping one testicle then the other into her mouth and holding it there for a few seconds while she ran her tongue around the scrotum. The feeling was sensational. It felt comforting, as though she was taking care of me. I had never felt such a thing with my former girlfriends. Josie was a champion.
Next, she pulled me even further off the edge of the couch, lifted my legs in the air and proceeded to lick my anus. “Oh my God!!!”, I thought as she darted her tongue in and out of me. I had a momentary feeling of embarrassment, and then thought that she wouldn’t be doing this if she didn’t like it. In fact, she seemed to be loving it; kissing my butthole and licking me like there was no tomorrow.
Moments later, Josie stood up and took my hand, pulling me toward the bedroom. I followed her willingly when she told me to lie face down on the bed. She stripped off my panties, lifted my butt in the air, and I could feel a silky liquid running down my crack. I knew I was about to be fucked, and I was all for it. She worked the liquid gel into my hole with her thumb while I remained motionless in anticipation. I heard her undoing her gown and stripping out of her panties, and then I felt a throbbing knob pressing gently into my anus. She pushed and pulled gently and rhythmically at first, until my butthole relaxed and opened enough to let her in. She slid into me with ease, at which I was somewhat surprised but very happy at the same time.
Josie asked me for confirmation that everything was ok, to which I practically squealed an enthusiastic “Yes!” She started pumping slowly back and forth until she was able to move freely in and out of me. After a few moments, she reached around my waist and grabbed my penis in her right hand. She rocked back and forth, simultaneously filling me with her delicious meat and stroking my longing shaft. We moved in unison for a while, and then I heard her starting to groan. She pulled tightly at my cock, squeezing it more and more with each thrust as she pumped her huge load of cum inside me. The feeling of her hot juices streaming inside me set me off as I shot several jets of my own all over the sheets with each successive tug from Josie’s agile hand.
“Did you enjoy that, Emily?” Josie asked my softly as we collapsed side by side on the bed.
“Wow”, I responded, “I never realized it could be that good!”
—
Josie and I met up a few times after that before I returned to Europe, and even though we enjoyed some more girly fun times together, that first time remains my fondest memory. I never did work out how she knew I crossdressed, nor that I would enjoy engaging in sex with another crossdresser. All she would tell me is that she somehow knew from the first time she set eyes on me.
