Liisa’s Story

(Editor’s Note: Sexual content ahead.) One of Linda’s volunteer duties with a local TG support group is to interview prospective members to try to weed out the ‘lurkers’ and disingenuous people before the group starts sharing confidential information with them. Members like to know that access to their photos and e-mail addresses is only for those who have been screened.

My motivation for doing the screening is that I get to meet some people with very interesting backgrounds and I get to dress up. I also get to share my own particular views on crossdressing.

Frankly the prospect of the screening process itself weeds out most of the ‘undesirables’ although I’m told one of our girls was able to block a local news reporter who was faking his TG inclinations to try to infiltrate our group.

But I am digressing. One of our new girls has given me permission to tell you her story so long as I change a few names and places. However I think she is a bright and fascinating gal and you will be hearing a lot of her in the future. I wish I had a photo to show you.

We met in a local restaurant. I was dressed en femme but Liisa was in male mode. ‘He’ was a very good-looking man of about 50, slim, 5′ 9 or 10″ whitish blond hair and virtually no sign of facial hair. I thought “give me my make-up kit and this would soon be one gorgeous lady.”

Liisa is of Finnish descent. She was raised in a northern Ontario town known for its forestry and mining industries. As she describes it she now lives in a large metropolitan area with her wife, pet dog and two children who occasionally come home from university and/or broken relationships.

“So how did you get in to crossdressing?” I asked.

“I’m not one of the ‘I knew from the age of six’ people,” she started. “Where I come from girls were girls and men were men,” Liisa continued using the line from an old TV show. In high school I played all the sports — ” basketball, track, I tried football and being Finnish my folks had me out on cross country skis as soon as I could walk. I did pretty well academically, too. My parents kept me on course to go to university. Up home that meant making sure I was careful with my girlfriends. For many of the local girls their aim in life was to get pregnant in their last year of high school, get married and take care of their guy while he earned a meager living in the mine or mill. My parents kept me out of that trap by making sure I was busy working in Dad’s business after school and that I had summer jobs out of town. Frankly I loved the work and didn’t want to get married anyway.”

“Smart guy,” I said thinking back to my own too early parenthood and resulting marriage.

“Well the summer I graduated high school my dad arranged for me to work for a friend of his in Toronto. I took the train the day after my exams finished.

“Mr ‘Smith’ met me at the Union Station. He was a really nice guy, very friendly. He told me I could get a place of my own but that until I was settled I was welcome to stay at their place. His wife and kids had just left for the summer to stay at their cottage in the Muskoka region.”

“That was nice of him.”

“But first he took me to dinner and we had a few drinks. He told me that we’d have to spend the night in a hotel as he was having some painting done in the house and he didn’t like the fumes. He had a room reserved in the Royal York. I must admit I was pretty tipsy when I got in to bed.”

“I think I know where this is going,” I interjected.

“No, he was a real gentleman. We each had our own bed. He got in to his bed. After a while he said in the dark ‘unbelievable but true.’ He said it again. I asked what he meant by that. He hesitated and then said something about the twists of life being ‘unbelievable but true.’ I could only meekly agree.

“We eventually went to sleep, awoke the next morning, had breakfast and went to my first day at work.”

I was starting to think that Liisa was leading me down a very long and winding road.

“After work we went to their house. It was in Rosedale and was about the nicest house I’d ever seen. Strangely there was no sign of any painting being done. John showed me to the guest room, suggested I shower and he’d have dinner ready for us.

“We ate, shared a bottle of wine and some good conversation. He was treating me like an adult. I really felt comfortable with him.

“After a while he asked if I’d like to go for a swim. I said I didn’t have a swim suit with me. He produced two of the skimpiest men’s swim suits I’d ever seen. I mean there was less material than in a racing suit. “Try one of these,’ he offered. I picked one and slipped it on and we went to their indoor pool. I was slightly aware of him eying my body.

“John stripped naked and dove in. I kept my suit on for a while and then it just felt natural to go naked as well. We swam around and chatted by the side of the pool. John suggested I try putting my groin against the water jet. That felt neat and as he sat on the deck next to me I felt myself glancing at his penis and getting a little erection. I didn’t understand why it was happening as I wasn’t gay or anything but I wasn’t revolted either.

“John must have known what was happening down below because he slipped in to the water beside me and asked ‘do you mind?’ and put his hand gently on my bum. I said I didn’t mind but really I only let him because he had given me a summer job and was letting me stay in his house.

“After a while he pulled me close to him and put his face in my neck. He grabbed my penis. I started to pull away but then stopped. Not only did I owe him something but his hand felt good. I was getting a hard on.”

“So am I,” I interjected.

“We stayed like that for a while then he turned me to him and kissed me square on the mouth. It was a forceful kiss, not like the kind I’d received from my girlfriends. He told me I was so beautiful and that he didn’t know why but he wanted to suck me and make love to me. I wasn’t sure what would happen next but I was pretty sure it would involve the two of us going to bed. I also wasn’t sure what would happen if I said no so I went along with him to my room.

“Naked and barely dried he lay me down on my back and knelt over my cock, taking it fully in his mouth and thrusting up and down. Then he turned around on the bed so I had a clear view of his cock. It was much larger than mine and beautifully cut. I took it in my hand and moved so I could also suck him. I instantly loved the textured feel of his cock in my mouth. I wasn’t sure how I would feel about it in the morning but for the moment I enjoyed it. We stayed like that until I came in his mouth. He then got up to rinse himself out in the guest bathroom and masturbate while I went in to a bit of a shell.

“In a while he said goodnight and that we’d talk in the morning.”

“How did you feel?”

“There’s no doubt I had questions about what had happened and what the future held for me. However, through the night I realized that I was still the same hetero guy I’d always been. I just had added a dimension to my life’s experience.

“At breakfast and on the way to work John didn’t mention the previous night’s activity. On the way home he said we had to have a talk. I thought, ‘Oh boy, this is it. He’s had regrets and he’s going to fire me with a story of how I came on to him’.”

“My guess is that he didn’t.”

“Right again. We ate and shared another bottle of wine. John told me about his life and how he’s been just like me at my age when an older guy had come on to him. He had enjoyed it then put the experience behind him as he got on with his business life and his family life but every so often he got an urge to play with a young man. I just happened along at the time of one of those urges. He explained that when he said ‘unbelievable but true’ he was thinking that he had really wanted to have sex with me right then and there in the hotel but unbelievable to him he was holding back.

“He asked if I’d had any regrets about the previous night.

“I said I hadn’t, that I knew it wouldn’t change my life and that I’d only regret it if he fired me. ‘There’s no question about that’, he said, ‘in fact if you stay here with me the summer and keep our little secret I’ll treat you very well.’

“So we settled in to a routine of working by day and playing every once in a while by night. Every so often John would leave an envelope with a few hundred dollars on the table beside my bed. In a few weeks I’d gone from track star to boy gigolo.”

“I assume the crossdressing comes in to it somehow?”

“Yes, when we were having sex John kept saying how beautiful I looked. He seemed to like my fine Finnish features. He suggested I let my blonde hair grow out and said I’d make a beautiful girl.

I kept thinking about his flattery. Every weekend John would leave to be with his family at the cottage. I had the run of the house. It wasn’t long before I started going though his wife’s drawers and trying on her lingerie and in to her closet to pick out a nice outfit and a pair of heels. They were a bit tight on me but they fit. I would sit around the house and do a lot of looking in the mirror. The session always ended with me masturbating and rushing to put everything away.”

“Been there; done that,” I said referring to how I used to try on my first wife’s clothes when she wasn’t around.

“Well, it seems one day I wasn’t so careful putting every thing away and John found a bra partly hanging out of his wife’s drawer. He asked me about it in a non-threatening way and I confessed that yes, I had been trying on her things. He told me I had to be more careful and he asked me to show him what I’d been wearing. He asked me to smell them and I discovered that I was leaving a scent behind. He put everything in the washing machine and then took me to bed. He wasn’t mad. He told me that the next day he’d have something for me.”

“I bet it was a negligee.”

“It was better than that. After work we drove to the Dufferin Mall out in the west end.”

“I know that one. It used to have a wig store,” I interrupted.

“That’s the one. Our first stop was Zellers where he asked me to pick out a couple of skirts and blouses. I protested that I didn’t know my size. He asked how his wife’s clothes had fit. I told him the skirts were fine but the dresses and tops were a little tight. He told me to get a 10 in the skirts and 12 in the tops and that if they didn’t fit we could always return them. Our next stop was the lingerie area for bra and panties. He also suggested I get a little pantie girdle with garters attached. He picked out some stockings for me. Shoes were easy. His wife’s size 9s fit me pretty well so he got me a pair of black patent leather heels and a pair of flats ‘in case you want to go out’, he said. At the time I laughed at that.

“We checked out our purchases and John paid cash. He confided that it wouldn’t do for his wife or the company auditor to see any of those charges on his credit card statement.

“Our next stop was the wig shop. They had a private booth for try-ons. John didn’t try to hide that I was his boy/girl toy. I guess the business was gay-friendly because we got great service and I got a beautiful Farah Fawcett style wig.

“One more stop at the drug store for some cosmetics and we were off to home.”

“I bet this was hitting you like a hurricane.”

“Sure it was. Part of me was asking myself why he was doing this and part was anxious to see what I looked like as a woman.

“When we got back to the house John told me to try on what I would like while he whipped up something to eat. I carefully laid out my clothes then put on panties and the bra. The panties proved a little difficult as I was already erect.”

“Surprise, surprise.”

“Next came my skirt and blouse. They fit well and so did the heels. I didn’t do anything with the makeup but I put on the wig and tried to brush it a bit. I looked in the mirror and was a bit disappointed. I didn’t look as femme as I thought I would. It was time to see what John thought. I walked awkwardly in to the kitchen. ‘Not bad’ he said and gave me a little kiss. Then he added ‘let’s eat and then I will help you a bit.’

“We ate a quick dinner, saying very little. When we were finished he asked if I was ready for some help. Yes, I replied. ‘Okay, how’s your penis?’ he asked.

“I told him it was soft. He told me to take it push my balls up between my legs and pull the scrotum to the rear over them. I followed his instructions and was surprised to learn that there was a cavity in the hips where the balls could be tucked away. With my penis tightly tucked away he told me to pull my girdle over them. That was lesson one.”

“Lesson two was to pad out my bra. “Rolled up socks will do for tonight but if you like we can get you some breast pads,’ he said. I got two pairs of my gym socks and rolled them in to a ball placing one in each cup.”

“Lesson three was the stockings. John had bought me a pair of beige nylons and one of black lace. I opted for the black lace pair. He showed me how to roll them and then unroll them up my legs and how to do up the garter clasps.

“Lesson four was how to shake out my wig and gently comb out the ‘Farrah curls.’ I took a look in the mirror. It was getting better.

“Fifth he gave me some hints on how to walk in the heels. I placed more weight on the balls of my feet and took much smaller steps than usual. Soon I had a bit of a hip wiggle in my step. It came easily to me.

“That left the make-up to do. John said that with my fair skin and near invisible beard I didn’t need any foundation but he put a little color on my cheeks, applied some liner and mascara to my eyes and showed me how to apply lipstick. He told me that before long I would be doing it for myself. I wasn’t sure that I would be ever doing it again but once I looked in the mirror I nearly fell in love with myself. The wig, padding and especially the make-up had made all the difference. I hardly recognized myself. I loved it.

“John loved it, too. He stood behind me at the mirror and brought out a final surprise. He placed a necklace around my neck and put matching diamond like earrings on my ears. “Wow was all I could say. Wow was all he could say.”

I added, “Wow”

“We kissed and it felt somehow different. Now that I was a woman John’s kisses were gentler, so were his caresses. I put my arms around his neck and hugged him as a woman would. I thrust my hips against his.

“He asked me if I would like to dance and for the first time I was aware of the music playing in the background. It was slow and romantic. We danced around the living room and back in to my bedroom, falling together on my bed. The rest you know; only this time when we stripped he got me to put on my negligee. I agreed and from that evening on for the rest of the summer I always wore a negligee to bed.

“So for the rest of the summer I spent my days as Lars the apprentice salesman and evenings as Liisa, the kept mistress.”

“Did you ever go out?” I asked.

“Not with John but when he would go away for the weekend he would tell me I should go to one of the gay bars in the Church/ Wellesley area. It took me a bit of time to get up the nerve but one weekend I went for it. I walked to Bloor Street and then grabbed a cab to Christine’s.”

“I knew that place, too.”

“It was a pretty lonely evening. I bet as a guy I would have been hit on big time but that was in an era when ‘queens’ were pretty low on the gay social ladder. If you didn’t have a mustache you were nobody.”

“I remember it.”

“The queens who were there were pretty cliquish and seemed to avoid me. Finally one came right up to me and asked if I was a cop. I laughed but apparently they were suspicious of strangers and they were afraid of being picked up for turning tricks. I assured them I wasn’t a cop but I don’t think they were convinced. So I left and enjoyed the evening air walking back to Rosedale.

“The rest of the summer I pretty well stuck to going to work with John, getting dolled up and going to bed with John and spending my weekends alone. Come the end of the summer I spent some time moving my stuff down to London getting ready for my first year at Western.”

“Did Liisa go with you?”

“No she didn’t. It was funny but as the summer was winding down John became testier with me. When his family was due back he moved me to an apartment hotel for my last week. He said he would visit me but he never did. I wasn’t invited to meet his family.”

“That would have been really strange.”

“I think I could have handled it. Of course I would have been Lars. I also think they must have been curious about what happened to the guy who’d been staying in their house all summer.

“It ended with me going up home for a few days over Labour Day and then heading straight to London. Most of my Liisa stuff got packed in a box and left at the Sally Ann. I kept the wig for a while but life moved on. I joined the Western cross country ski team and became quite a jock. My hetero tendencies came back to the fore and I had no shortage of hot athletic co-eds to play with.”

“Life was good for you?”

“Life was very good. I married, started a family and got a series of good jobs. For while I was in politics but business and investment were in my blood. I’m pretty well my own boss now.”

“So what brings you to me?” I asked.

“I was browsing the web and saw an article about John. He died several years ago but he left a legacy of philanthropy. Reading about him got me thinking about our summer together and about Liisa. I realized that I missed being en femme. I did a little more research on the web. I experimented with some of my wife’s clothes and now I want to find out more. I think the best way would be to join your group and attend some meetings. I want to see what I’ve been missing”

“Well you would certainly be welcome if it was up to me. I will recommend sharing with you when we next meet. Would you like to come as Liisa or Lars?”

“I’d prefer to be Liisa but I haven’t got any outfits and I don’t think my wife is ready to know about this.”

I responded by offering something I’d never done before. “When I go to a meeting my wife insists I get a hotel room so I don’t leave from the house. Next meeting why don’t you join me? We’re about the same size so I will bring you an outfit, an extra wig and some fresh make-up.”

“I couldn’t ask you to do that,” he replied.

“It would be my pleasure.” I resisted adding that perhaps I would get as lucky as John had done but that was what I was thinking.

The End

Category: Transgender Fun & Entertainment