A Weekend with Samantha

As I passed the sign for The North I felt excited. Traffic had been heavy getting to the motorway and represented my virtual journey to this point in my life. As I turned onto the motorway slip road I could see the road ahead was clear so I changed up a gear and put my foot down to accelerate and join the main carriageway.

I was heading north to meet my friend Samantha, a crossdresser in her late 40s like me. We had met online a few years earlier when I was rediscovering my love of crossdressing and my kinks. I had been crossdressing since my late teens, like most trying on my sisters and mother's clothes, and later acquiring my own wardrobe as I went through my twenties enjoying periods of singledom. When I met my wife I knew I had to discard my femme life and so the weekend before we moved in together I reluctantly took my femme wardrobe down to the local charity shop and begrudgingly said goodbye to a selection of evening dresses, office wear and nightwear. My wigs and make-up went in the bin as I said goodbye to Susan.

Whilst I felt sad back then I don't regret it as I have a happy married life. In recent years as our children have grown up and our sex life has naturally waned I found myself thinking back to those crossdressing experiences in my twenties and craved to be Susan again. Time online soon introduced me to social media specialising in crossdressing and soon I had created a new profile and was chatting with others. As time continued I noticed chat was limited as other people craved to see pictures of me and I started to acquire a new femme wardrobe. We owned a big enough house by then that I could hide the items away and bring them out as required. I contacted a local photographer who agreed to take pictures of me en-femme and once the new pictures were uploaded I started to notice that I was more popular.

Eventually, chat with others moved on to talk of physical meets and I was transported back to my early twenties and the delight of seeing an attractive crossdresser and then having the further delight of seeing their cock as it was revealed from under their skirts and released from their femme panties. I liked to submit in these scenarios, taking the cock in my mouth and later feeling it pushing and entering my bottom and the eventual climaxes that the sexual play brought. As I chatted to other crossdressers I yearned for these meets again and knew I had to do something about it.

When I told my wife she was understanding and said that if it was what I needed so be it. I had confessed to my crossdressing during the early stages of dating but I had not wanted to continue it as our relationship progressed. I knew my wife had explored her own fantasies before we got together so I knew she was open-minded. Meets took place after that with local CDs. Some would involve just chatting but some led to sex and I submitted to them like I did in my twenties. As time marched on my femme wardrobe increased in size and I had more photos taken which boosted my profile. As I was enjoying this newfound life I met Samantha.

I was attracted to Samantha's overtly sexual photos she posted on her profile. Whilst they didn't display genitalia, she posed in tight office wear showing off the curve of her bottom and the curve of her breasts through the shiny fabrics she liked to wear. She was an attractive woman in the various blonde wigs she wore and well-applied make-up. I fancied her from the off and wanted to get to know her more.

I wasn't expecting a reply to the message I sent her complimenting her on her look as she was clearly popular, having a lot more likes and comments on her photos than I could ever hope to achieve. I was surprised when later that day I received a reply from her thanking me for my compliments and also complimenting me on my own photos. A few days later I bought myself new office wear consisting of a deep red satin blouse with a black leather knee-length skirt and booked myself in for another photo session a few days later. When the photos came back I shared them with Samantha who was very complimentary. The regular chat continued and eventually, she asked if we could meet.

Samantha lived a couple of hours away from me so I knew that I would need a night away and told my wife. She had become very understanding of my needs and so would give me a proper goodbye with a hug and kiss before I left and so I felt happy and confident as I set off to meet Samantha. The meet took place in Samantha's house as her wife had gone out for the night. We spent time getting to know each other by chatting and eventually we moved to sit next to each other and soon had our hands all over each other. I left the following morning having experienced Samantha's climax in my mouth and bottom and after a very satisfying hand job from her where my cream ended up all over her fingers. We savoured the taste of my juices by licking her fingers and then enjoying some long deep post-play kisses.

The meet had been very successful and Samantha asked if I was willing to have a longer meet a few months later. A friend of hers owned a cottage in a village near where she lived which offered us privacy but also enabled us to spend time outdoors dressed, something we both confessed to wanting to try. The first weekend meet at this cottage was a huge success as we enjoyed plenty of time in vanilla mode and playing in bed together. Subsequent meets took place every three to four months and we had become more adventurous with going out together dressed such as to a local restaurant to eat.

A few months had passed since our last meet and I was relishing the weekend ahead with Samantha. I had bought some new outfits and finally treated myself to some new nightwear. The journey on the motorway and to the cottage was easy allowing me to arrive close to our meeting time. From outside I could see lights on and I headed to the back door to let myself in and change inside the kitchen. When I was ready I went through the sitting room where the lights were dimmed and a fire lit. Samantha came forward with a glass of Champagne and our mouths met as we kissed and pushed our tongues together allowing a short French kiss before we broke away and enjoyed the Champagne whilst catching up.

Catching up soon led to kissing and heading upstairs to bed. Both of us are of an age where undressing each other on the sofa is for teens and it is far nicer to head to the bedroom, change into clothing which can be easily removed and enjoy each other's bodies. Soon, we were in bed together and I was very pleased with how the silk of my new nightwear rubbed against my hairless skin and Samantha ran her hands over the outside, allowing me to feel her fingers through the thin fabric covering my body. Samantha's hands continued exploring and moved up under my skirt touching my thighs and moving ever higher.

As Samantha continued to touch me lightly it became too much and I broke away from her mouth laying back allowing her to continue exploring my body as my breathing intensified. As Samantha's fingers moved higher and touched the fabric of my panties with the sensation being felt by my cock I felt myself have a mini climax, erupting an amount of cream from the end of my semi-hard penis. Samantha sensed my climax and so moved in close to me, allowing us to cuddle and gently kiss each other. We were both tired and so happily fell asleep afterwards.

The following morning I woke before Samantha and went downstairs to enjoy some time to reflect. Sitting down in my femme nightdress and robe was lovely and I savoured the sight of my hairless slim legs and reflected on the pleasure of enjoying Samantha's intimacy and comfort in the bed the night before. I drifted into a daydream and was awoken a little while later when I heard Samantha moving around upstairs so I returned to join her. When she saw me she climbed back into bed and I joined her as both of us were much more awake and keen to continue with our sexual relationship. We started kissing and soon I broke off to move down under the covers and explore Samantha's groin. I lifted her nightie and pulled her hardening cock out of her pants feeling it spring free in my hand. In the gloom under the covers it was difficult to see the full splendour of her thick rod, a sight which has always attracted me to her and which I always wish to put inside my mouth as soon as I see it.

I started my oral sex routine of licking the tip and savouring Samantha's moans as my tongue flicked over the sensitive end until I felt it was getting too much for her. I then started to guide the rod into my mouth, savouring the feeling of the shaft entering my mouth and allowing me to mouth fuck her. As it touched the back of my throat and my gag reflex kicked in, I started to slowly withdraw it until the tip emerged from my mouth and I gently kissed the end again. I repeated this several times while Samantha got more and more excited. Once I knew she could take no more I started to slide the penis in and out rhythmically, fellating her hardness and bringing her up to her climax. I felt her squirm and was rewarded with waves of cum erupting from the end and filling my mouth. I knew Samantha liked to taste her own juices so I swallowed most but kept some back for some final post-coital kisses before we lay back in each other's arms and fell back to sleep. As I drifted off to sleep I craved Samantha's rod inside my bottom but we still had plenty of the weekend to go and that would come later.

We woke later in the morning and spent time enjoying breakfast and dressing. Samantha wanted some new video of her dressed so she changed into her trademark smart officewear and I nearly came when I saw her come down the stairs. She had a pair of black patent heels on her feet but it was the combination of dark green satin blouse and leather skirt that nearly made me come. Despite us both approaching fifty we have kept our bodies in good shape and Samantha's form inside this smart ensemble made me want to molest her there on the spot as she looked gorgeous. As well as the footwear and clothing she had selected a new lighter blonde wig with silver highlights and applied make-up to match. I was really turned on by the sight of her and asked her to stand there while I looked at her. She did a couple of turns so that I could take in the stretch of the leather over her shapely bottom and the back seams of her stockings.

"Can I touch you," I asked? Her reply left me mildly disappointed as she said that I would have to wait until later as if I started we would never get anything done. We then set to work preparing to photograph and video her. Samantha had started to make more content in recent months as she had found it was a good money maker. During our weekends together over the past year we had started planning and then filming her for her fans. The content uploads had increased her following and she was starting to make good money from it. She had confessed that if her wife accepted it, she would become Samantha full-time, quit her job and just make content. She knew that was probably not going to happen and so she confined being Samantha to meets, these weekends and sharing her experiences with her fans.

We got to work setting up the lighting and cameras and started filming Samantha. We began with Samantha fully clothed but teasing and saying words she knew excited her fans. She gently brushed her fake breasts through the satin of her blouse and then seductively uncrossed her legs giving the briefest glimpse of the area between her legs which remained in shadow. I was smiling as I filmed her and reflected on how professional she now looked when being filmed but also I wanted to put my hand up between her legs and feel her. We took our time and then broke for a while before moving on to the second set. This involved Samantha unzipping her skirt and showing her bottom off to the camera. With her skirt open there was a good view of her stocking tops and she gently stroked these knowing it would make her fans go wild. The third set was much more explicit as she removed her pants, making herself hard and then stroking her cock as she talked dirty into the camera. She never climaxed in these sets as she wanted to tease the viewer and exercise her status as a Domme. She had also started doing private cam sessions where she would climax on camera and knew she could charge a premium for this service. I was glad as I wanted her cream for myself later.

All of this filming as well as photos took a few hours so we finished up for lunch and decided to go out afterwards. I was desperate to go walking nearby as I had recently acquired an autumnal country lady ensemble of raincoat, jumper, long tweed skirt and brown boots. I changed and presented myself to Samantha who was impressed. She was more casual in leggings and a fleece and her wearing casual clothes made me so jealous as her body shape suited them much more than I could ever imagine. We headed out into the street and soon turned off onto a path and headed across the fields. I loved these outdoor excursions as they made me feel liberated and the woman I wanted to be. I liked dressing up in smart wear but if I wanted to really be Susan I knew some more casual attire and looks were needed. Despite the wind and threat of rain we both felt great linking arms and walking through the countryside and enjoyed most of the walk in silence as we were happy being who we wanted to be.

In the evening Samantha had arranged a bit of a treat as we headed to the local pub for dinner but with a twist as she had invited four other crossdressers she knew well to join us. A couple had driven over en-femme just for the evening while the other two had booked into the pub and so changed into their femme personas before dinner and joined us in the restaurant area downstairs. The pub had a separate dining room for us and we took our seats and started to enjoy the company of the evening. I had met them all before and so we caught up on what had been happening since we last met and then the others wanted to hear about Samantha's content creation and how it was going. They had all been following her on social media and had seen her photos and videos and wanted to know more. Both Samantha and I spoke about our filming session from earlier in the day as the other sat there in silence.

"Do you need any subs to film?" "How can I be in one of your videos?" "Can we come to the next filming session?" These were all questions that were asked. I felt a bit embarrassed at all of this as I knew Samantha had sex with other crossdressers and a monogamous relationship with her wife but I always liked feeling that she only had sex with me. Samantha sensed this and answered that at present she would only make content with me and at this I visibly relaxed. The evening continued and eventually wound up with Samantha sensing some of the others wanted to come back to the cottage but I knew she was feeling horny as was I and we wanted to get back for more fun. We said our goodbyes and almost ran back to the cottage where we undressed and started embracing before Samantha broke off telling me that she had a surprise for me. We went upstairs where I was told to close my eyes and could hear rustling and metallic sounds. When I opened them she was holding an assortment of equipment and I knew what was coming.

I have always been a fan of bondage and as my relationship with Samantha has developed she has helped me explore my fetishes of being tied up and fucked roughly. The cuffs were old but the ballgag and hood were new. She helped me put the cuffs on first and left them unsecured while she placed the ball gag over my head securing it in place with multiple straps to secure it in position. Next came the hood, another new purchase which she placed on me before I felt the back laces being pulled together, pulling it onto my face. Straps over the eyes, under my chin and around my neck secured it fast and the extra security of small padlocks fastened to the buckles prevented me from undoing them. As I was placed into this head prison I became very conscious of my breathing and the sounds around me.

Samantha roughly manoeuvred me onto my front and secured the wrist and ankle cuffs with heavy-duty equestrian snaps. I then felt cold lube being applied to my bumhole and the weight of her body lying on top of me.

"Getting ready fag for some big cock action," I heard her say through the thick padding of the mask over my ears which excited me. I felt her move to line her cock up with my bottom and she started to press herself against my opening. My sphincter naturally resisted for a moment before dilating and allowing her inside me. Once she had got comfortable she started to ride me and hard. Samantha knows that I like rough anal sex with the feeling of the giver pressing down on me, pushing my head down into the pillow and making me take her full length inside me. She used her other hand to push my body which combined with my bonds made things uncomfortable but I enjoyed it like that as it fucks my mind as much as my body. By now Samantha was in full domme mode, fucking me and using her spare hand to spank me as she took breaks in her thrusts. This continued for what seemed like an age before I felt her body spasm and her climax pour into me. Wave after wave of cum erupted inside me and I was glad we had saved this moment for later in the weekend.

I was totally weak afterwards and continued to submit as Samantha removed the hood from my head and then the cuffs from my wrists and ankles. She made me climb into bed and cuddled up close to me, pulling the duvet over us both. I always love her post-play care of cuddles and gentle kisses and this is how we fell asleep.

As I woke up on Sunday morning I felt sad knowing that Samantha and I would say goodbye again later. Samantha woke shortly afterwards and her instinct told her that despite all the fun so far over the weekend, I needed my own climax too. She cuddled me closely and moved her hand down to free my own cock from my panties which was semi-hard in the morning. She started to stroke me, gently teasing my cock with her long nails and gently nuzzling me. My own climax was soon in coming as I had abstained from wanking for a couple of weeks before our meet plenty of cum was released and most of it ended up on Samantha's hand. We were both spent by then so we cleaned each other up and set about preparing for the day ahead.

The two crossdressers who had stayed over in the pub joined us for brunch and it was nice sitting in the cottage's kitchen in more casual wear talking about experiences of dressing. Eventually, we knew it was time to end the party so we cleared and packed. Samantha and I had one final embrace and tearfully we said our goodbyes not knowing when we would meet again. I returned to the kitchen where I changed back into male mode and left the house for home. Heading home was hard but I knew that once back I would go back into my male persona and would be fine until the itch to meet Samantha started to grow and another meet was necessary. My wife welcomed me with an embrace and a full kiss which made me feel better and want to step back into family life.