My mom and I had established a routine after we “came out” to each other. Seems we both loved wearing feminine undergarments and we loved wearing them while we masturbated and sucked each other. I’m the middle-aged son in the basement apartment and she’s the sixtyish mom upstairs and we have a monthly date when we get dressed in our finest lingerie, open a bottle of chilled Prosecco, cuddle for a while and then let our fingers do the walking until we’re both well satisfied, often satisfied a few times. It was all going swimmingly until mom’s boyfriend got involved. I hadn’t mentioned him bec… Read more

A Cum Filled Afternoon Overlooking Vaseline Towers I'm thrilled that I'm making this step towards greater crossdressing thrills and more excitement. I've accepted an invitation to “drop by” the hotel room of a new cross dressing friend next time he's in Toronto. He'd posted this invitation to all 12 million xh users. but somehow I think I may be one of a few to show interest. Right now I'm very interested and I await the day when our stars align (preferably our cocks). For me,it will be when I go to TO for one of my regular visits to friends and to visit art galleries and maybe stay into th… Read more

My friend Steve invited me to a party. We’d been chatting about it for a while. He called it a “stroke and cum” party. The way he described it, it was older men mutually masturbating. There was usually about a dozen participants and it took place in a hotel room downtown whenever someone in the group organized it and sent out invitation. Steve had received the invitation forwarding it to me. I accepted and we agreed to meet near the venue. I should bring $25 towards the kitty to pay for the room and some booze. Underwear was voluntary because it got in the way. I was keen. We met then made… Read more

I was in grade five and today had not been a great day. My mother was going to make it better though and change my life. I came into the living room to find my mom, as usual on her chaise watching TV. She was dressed as usual in her housedress. She noticed my distress and asked what was wrong. I said some k**s had been mean to me. She urged me over to her chaise and I lay across her rather large body, my head on her big round breasts and she rocked me "There, there now, Mommy's going to make you feel better." She reached up, opened the top buttons of her housedress and opened her nu… Read more

Cocksucker’s “To Do” List I regularly chat and cam with other men who wear women’s clothing, men who love to perform for each other in sexually explicit ways. We enjoy each other and our small group has become a sort of club since we are geographically and sexually close. A leading member of our “club” organized a challenge and selected a number of us to attend a special “real” event. Three of us accepted the invitation. We would be meeting for an “opportunity” to perform the sexual goals that each of us had posted on our online profiles. With much excitement, I prepared for the gat… Read more

Ever wondered how a 69-year old retired photographer who likes to show off in panties came to be that way? Why do I have an irresistible desire to masturbate with men while in panties? I blame it ALL on my mother. I clearly recall the afternoon when I got home early from school and lay on my bed to play with myself. I was twelve and had discovered P...boy magazine and how my cock would get hard looking at naked women. I didn’t notice when my mother came into the room but when she said softly “I wondered when you’d discover that smut.” I froze. I quickly pulled a sheet over my withe… Read more

Pulling the Train with Mom My mom and I had established a routine after we “came out” to each other. Seems we both loved wearing feminine undergarments and we loved wearing them while we masturbated and sucked each other. I’m the middle-aged son in the basement apartment and she’s the sixtyish mom upstairs and we have a monthly date when we get dressed in our finest lingerie, open a bottle of chilled Prosecco, cuddle for a while and them let our fingers do the walking until we’re both well satisfied, often satisfied a few times. It was all going swimmingly until mom’s boyfriend got invo… Read more

Mother and Crossdressing Son Fantasy The story is about how my passion for wearing women's lingerie helped me to establish a more intimate relationship with my mother. I'm a 42-year-old man and I still live at home with my mother. My Father passed away 20 years ago. We live in a suburban bungalow and I have a nice little apartment in the basement. It's not as private as I would like. That's important because four years ago after discovering a number of chat sites where men present themselves in women's underwear, I began to become interested myself. Now, once a month, I dress in very fin… Read more

I'm wearing my new panties that I bought at Target. They're aqua which is a colour a tend towards mostly because Target doesn't have a lot of red panties in Large. My stockings are from Dollarama because I didn't have the nerve to search through other stores. Any way, they're hold-up stockings in a flesh tone and I like them. The self check-out at Target and other stores is a revelation. I could purchase what I wanted without passing through the watchful eyes of some s*******n-year old girl who clearly wonders, "what's this old guy is doing buying stockings and panties"? She'd joke with… Read more

An older man finds an older woman and her cock at a Spanish class. With winter coming to an end I was taking a class in conversational Spanish at the senior citizens centre because I planned to travel to Spain or Mexico next year. The people in the class were about my age, 60 to 70. I was fortunate enough to sit beside possibly the most attractive woman in the class. Unlike the others she dyed her hair a bright red and, come snow or sleet, she always wore a dress. For a number of classes we worked together trying out our poor Spanish until we could both ask where the toilet was, or order a… Read more

This morning, I had been on Live Cam watching a 25-year-old man with an enormous cock who gently stroked himself while receiving encouragement from at least 20 people. I went through the list of watchers and found the usual suspects. There were a few quiet Eastern Europeans, a couple of a teenage men comparing while trying out their gear, two women, suspiciously young with nothing on their profiles - and at three older men. I'm always compelled to comment on the Live Cam men and their penises and occasionally I get a private message. "Hi," usually starts the conversation followed by an inv… Read more

Being a pensioner with time on my hands and discount tickets at the local movie theater I'm there a couple of afternoons a week. This week though was going to turn into the kinds of activities at a theater that we only dream of. Alone in the dark with women strangers was just the start. I'd seen all of the action flicksd at the local movie house so I took a chance and went into a Disney movie. Maybe it was Lion King I'm not sure because what was going to happen to me gave me a whole new appreciation of Disney movies. I usually sit in the back is my eyes just won't work any closer. The t… Read more

I have a fantasy about masturbating with a friend when I was just a teenage. Actually, the fantasy is about how I should have - but didn't. A gay friend was to be my guide to fulfilling my fantasy. When I was about twelve, I had been a frequent reader of lusty stories and would get a dirty magazine whenever I could. I hadn't yet masturbated but had played with myself even poking my stiffening cock onto any hole I could find, mattress, rolled towel-anything to try it out but ejaculating was a mystery. One day the mystery ended when I took playing with myself to a new level and came for… Read more

I met a woman at a party last night and this skinny skank gave me the best sex without touching that I've ever had. It was the best climax in a most erotic situation, complete with porn, voyeurism and fantastic masturbation. And we probably haven't finished yet. I was attending a celebration of a local Neighbourhood Watch's fifteenth anniversary. I was invited because I was a friend of a friend and didn't get out much. Someone took pity on me. I was standing alone watching the men in shorts and t-shirts make pigs of themselves at the snack table, clutching warm beers and talking about… Read more

Part 5 during which I meet new friends who touch my cock and encourage me to ride my bike more. These weeks with my anonymous couple in the nondescript house on my bike route have been disturbing. Getting sucked off by both of them and accepting commands from them without any control on my part has been humiliating - and very exciting. I jerked off at home after these episodes and the orgasms were explosive. I had become a willing participant not knowing what would happen to me the next time I was called to their home and ordered to "strip." A few weeks later, after no contact from th… Read more

Part 4 during which I sucked the husband's cock and was introduced to another neighbour It was three weeks before I make contact with them again. I had ridden by their house every day and the lights were always off. I even tried the door. It was locked and when I knocked nobody answered. This was a very frustrating time for me. One morning I got a phone call from the husband. It was his familiar voice ordering me, over the phone, to take my clothes off. It was early but I'd been at the computer watching porn so I was already naked. I waited a moment to convince him I'd stripped then h… Read more

Part 3 in which I'm agreeable and cruelly disappointed. The next morning, before dawn, I got on my bike for my ride but this time I stopped in front of their house. I could see the flickering light from their television through front window. I walked up to the porch and tapped on the door. The man yelled "It's open. Come in." And I did. They were watching a video of me masturbating in front of them a week ago. They were both on the couch in a darkened corner I could see that they were naked. Don't these people wear clothes? Once again the house smelled of marijuana. "Come and sit do… Read more

Sex Slave to the Neighbours Part 2 This is Part 2 of 5 in which I go back to the house where I had been humiliated and excited, not to mention, got sucked off by an attractive older woman. The next morning with the sun just clearing the horizon, I jumped on my bike for a ride by that woman's house. The previous day had been a dream and a nightmare. It was all so sudden and I was rushed out of the woman's house so quickly that I didn't know what had happened to me. So, I'd ride by the house and maybe I'll get invited in again and get my cock sucked and my balls drained. Or maybe I'd… Read more

This is part 1of 5 Since retiring, I keep fit by riding my bike around the neighbourhood a few early mornings a week. Exercise is the excuse but my fondest desire is that, along my route, I'll get invited into the home of a mature woman who was waiting for a bike-riding gent to pass her home, come in and fuck her. Balls drained, I would then ride home smiling, maybe to return the next day for more. In this story, it goes way beyond that. Over a couple of months I would become a slave, have my cock sucked by the woman on my route, take her husband's cock into my mouth enjoy it and climac… Read more

This is part 1of 5 Since retiring, I keep fit by riding my bike around the neighbourhood a few early mornings a week. Exercise is the excuse but my fondest desire is that, along my route, I'll get invited into the home of a mature woman who was waiting for a bike-riding gent to pass her home, come in and fuck her. Balls drained, I would then ride home smiling, maybe to return the next day for more. In this story, it goes way beyond that. Over a couple of months I would become a slave, have my cock sucked by the woman on my route, take her husband's cock into my mouth enjoy it and climac… Read more