A Year with Anthea

In the early hours of January 1st, I split up with my girlfriend. It had been coming for weeks as I had grown tired of her narcissism and jealousy towards me. Matters had been bubbling up all evening and after we arrived home from a New Year's Eve party she let rip about the lack of attention I had afforded her during the evening and lack of reaction to her speaking to other men. I wasn't sorry and as I left her house and headed home I felt quite relieved. As we progressed through the month and she swiftly found a new boyfriend that she was parading around, I was happily enjoying the single life again and thinking about the future but wondering what lay ahead.

Being back on my own I started searching for porn online and one evening I clicked on a video showing an attractive woman in the thumbnail. As the video played out, the woman slowly stripped revealing tanned skin and small breasts. As she pulled down her pants she revealed a hardening cock. I had entered the world of transgender porn and I liked what I saw but wondered how to enter this world.

Fate intervened in February as on a Saturday evening I was waiting to start a shift of work in central London with two colleagues. We sat in the front of our van and while we waited we noticed a large number of people walking into a club across the road. As they entered we noticed that some of the women were walking like men and a few overtly dressed and made-up drag queens entered.

"That must be one of those weird clubs where men pretend they are women," one of my colleagues said. Whilst they sat there deriding people walking in I was quite intrigued as I watched various people entering including cross-dressed men, some alone, some with genetic girls who I reckoned must have been accepting wives, girlfriends or friends. Single men also entered, some quite smartly dressed for a night out and others with bags, probably containing femme clothing, using the club to get changed. We continued watching while we waited and finally, we were instructed to start work and my attention moved on to getting the job done.

Back home my search for information about transgender women widened as I started searching for crossdressers and started watching porn featuring men dressing as women and having sex. As well as searching for porn I searched for non-sexual content about crossdressers and learnt more about them as well as the term Admirer, a category I felt I fell into.

A couple of weeks later March arrived I was sitting in my car outside the club in a similar location to where I had sat in the van with my colleagues but this time I was dressed up for a night out and building my confidence up to go inside the club. Once I saw a few people head inside I left my car to walk across the road to the club where I paid the entrance fee for an Admirer and headed downstairs to the club area.

I had no idea what to expect inside and so struggled to think about what to do next. I knew a lot of transgender prostitutes and their pimps operated out of the club and I wanted to avoid them. I also knew I was facing tough competition from the other Admirers who came to the club looking to hook up with crossdressers and transgender women. I bought myself a drink and started to move around the room wondering what to do when I noticed a genetic girl sitting with a cross-dressed man beckoned me over.

"You looked a little lost," she said to me. She introduced herself and her cross-dressed husband. We chatted for a while where I learnt more about them and they asked why I was there. I told them that I was curious about crossdressers and when she pushed me I told her I fantasised about having sex with a crossdresser. Both of them looked at each other and I wondered if I was being set up but before I had to answer I was asked to dance with the husband. 'She' stood up and took my hand leading me to the dance floor. I enjoyed the feel of her hand which was soft and she had long painted nails. Her deportment was feminine and she looked good in the dress she was wearing. She danced in a very feminine way interpreting the music and making me feel at ease. We danced to three songs and then headed back to the table. This time I was the leader happily taking her hand in mine and threading our way through the crowds back to our table. When we arrived back I could see another cross-dressed woman had joined and I was introduced to her and when I asked her name she told me it was Anthea.

Anthea was a good-looking woman and had just turned thirty like me. She wore a chestnut brown wig falling just below her shoulders which I learnt was her favourite hairstyle. She had dressed elegantly but stylishly as she wore a black bias cut dress which emphasised her slim figure, fishnets and black low heels. I was also drawn to her hands which were slim with black painted nails and she had light but nice makeup. As she stood up to greet me and I shook her hand I felt a tingle inside me as I found myself fancying her but knowing that under the wig, makeup and dress was a man with a cock and balls. The question I had been asking myself for the weeks before and right now was, "am I gay?"

I sat with Anthea and chatted with her and liked what I heard. She was easy to chat with and asked me questions about my vanilla life, territory I thought was out of bounds at a venue like this, but she made me relax and willing to tell her more about me. I learnt that she was gay and liked men. Anthea had been born a couple of years earlier but it had only been in the last six months she had gone out dressed and had started visiting the club we were in at the time.

As the evening progressed I found myself enjoying Anthea's company and we were giving each other playful flirting touches. She put her hand on my thigh out of sight under the table and moved it higher and I happily placed mine on her fishnet-clad leg and gently moved it up inside her skirt, feeling the tops of her stockings but deciding to stop there.

I didn't want to snog Anthea here so asked her for a dance. I happily took her smooth hand and led her onto the dancefloor and we enjoyed dancing to a few songs where I was playful pulling her in and placing my arm around her back as we swayed to the music. The music later changed to the final few slow songs of the night.

As the first song got under way I pulled Anthea in towards me and moved my head to kiss her on the mouth which she responded to. As the music eventually wound up I was a mixture of emotions but knew I wasn't quite ready to take things to the next stage. Anthea invited me to come and join her at her hotel but I declined, said goodbye and headed home.

The year moved into April and Anthea and I were now chatting daily after meeting at the club. Eventually, I felt ready to meet her again and she invited me to her house one evening for dinner. I knew I wanted to be more intimate with her and have sex and just hoped this wasn't obvious when we met up. When Anthea answered the door and invited me in I wanted her straight away. She was wearing a bright print summer dress, a style she favoured, and tan stockings with light-coloured low heels. She invited me in and we exchanged some small talk while she mixed me a drink. As she passed me my drink, our fingers touched and I quickly put down the drink and moved in to kiss her. She responded hungrily and after we had started vigorously exploring each other's bodies she led me upstairs to her bedroom.

She sat on the end of her bed and lifted her skirt allowing me the sight of her matching underwear set. Her pants showed the bulge of her cock inside and she slowly pulled them down allowing her restrained cock to unfurl and harden. I knelt in front of her and took in the sight of her now hard cock, absence of pubic hair, and moved forwards, taking it into my mouth and started to suck her off.

My technique at sucking cock was rubbish and I could tell Anthea wasn't enjoying it and so I broke off and wanked her off with my hand. We happily looked at each other in silence as I gently tugged at her member in my hand and this was providing her with a lot more pleasure as she eventually lay back to enjoy the sensation, finally climaxing and ejecting her hot sticky load over my enclosed hand.

When she sat back up she saw the sight of her cream over my wrist and dipped her finger in it, tasting some for herself and then putting her fingers inside my mouth, allowing me to taste her cream, a first for me, and a taste I liked.

She led me into the bathroom to clean me up and then we headed back downstairs for some drinks and the dinner I had originally come over for. We chatted more after dinner and she asked lots of questions about me and why I had come over that evening. I told her I didn't think I was gay and she laughed saying that she had met men like me who like cock but only when they think it belongs to a woman. This made sense to me and later she asked me to stay and it felt lovely following her back up to her bedroom, undressing and climbing into bed next to her encased in her silken nightwear.

We both slept well snuggled up to each other and in the morning, as daylight started to appear in the cracks in the curtains I started kissing and touching Anthea and she asked if I would like to fuck her. I was hungry for her and she moved to position herself on all fours, allowing me to enter her bottom from behind. I wanted to savour the experience as long as possible so slid myself in and out slowly until I could finally hold back no longer and I emptied the contents of my balls into her bottom. I pulled out afterwards and we enjoyed a post-sex cuddle.

By May we were an item and my skills at both oral and anal sex had significantly improved. While we switched roles, I preferred sucking Anthea off and then releasing my climax into her. Anthea told me she loved anal sex and the feeling of my hard cock sliding over her prostrate. She introduced me to new positions including where she would lie on her back, placing the soles of her feet on my shoulders, allowing me to penetrate her deeply and meaning we could kiss during sex. This was her joint favourite along with entering her from behind such that the weight of my body pushed her into the bed making her feel very submissive as the sex felt very animalistic.

As June came Anthea asked if we could visit vanilla settings. She wanted to be Anthea in places other than at home or in TG/CD friendly clubs. I agreed to escort her out and we started by visiting a cinema, but soon found our attention moved away from the film and onto each other as we used the darkness to explore each other's bodies. As the evenings stayed lighter as we approached Midsummer, Anthea asked if I would escort her to the pub one evening. We drove to a country pub on a sunny summer's evening and I found a table outside where I suggested Anthea wait while I went to the bar to get some drinks. When I returned Anthea looked uneasy. She had been given some funny looks by people on nearby tables and we both found conversation strained. The final straw was a comment from a group of lads nearby and we abandoned our drinks and headed back to Anthea's. She was upset as we arrived back at hers and both felt it was better if I left her alone for the night so I headed home, also feeling upset.

In July Anthea wanted to try going out in a vanilla setting again. This time I suggested we take a walk in the countryside and enjoy a picnic as we both felt nearby towns and cities were too crowded. She wore a tight-fitting cotton dress and trainers. She had hairless legs meaning that she didn't need to wear tights or stockings all the time. We drove out to a nearby canal on a sunny day and found the car park busy so it took a few moments before Anthea was ready to leave the car but eventually she did.

We held hands as we walked along the canal, passing many pedestrians and boaters and as we kept walking Anthea visibly relaxed and eventually had quite a carefree look. When we had walked for a while I suggested we take a detour and we found a nice spot overlooking the canal and countryside.

We enjoyed our lunch enjoying the company of each other and not needing to speak much. We sat holding hands after finishing our food and soon started to stroke each other and a desire to have sex built up inside both of us. I suggested we move into a nearby set of woods and Anthea gave me a look indicating she felt the same way. We quickly packed up and headed into the woods, following a path and then moving through trees to a clearing where I spread out the rug and we continued to release her passion. I lay Anthea on her back and at a suitable point I removed her pants as well as my shorts. I pressed myself against her bumhole and felt resistance until she dilated allowing me inside. I started to fuck her slowly, allowing myself to kiss her and enjoy the moment as we savoured the intensity of our passion and the sounds of nature around us. I wasn't hurried despite having sex outdoors and I held back my climax as long as possible but eventually couldn't hold back any longer and ejected my cum deep into Anthea's bowel.

The success of the picnic and some other outings led to Anthea suggesting we go away on holiday in August. I still wasn't ready to see Anthea in male mode and she wasn't happy travelling abroad en femme so we agreed to stay in Great Britain and rented a cottage in Wales for a week. Anthea was so excited about spending a whole week en femme and so went on a major shopping spree beforehand to buy enough femme clothes, underwear and makeup for a week away. We enjoyed the week away as we knew we could enjoy many successive days and nights together rather than snatching weekends, often having to sacrifice time together to spend time with our respective friends and families who still didn't know about Anthea or my desire to be with a crossdresser. A holiday removed all of these issues and we enjoyed a week of what life could be like. We spent most mornings lazy around in our nightwear and spent the days sightseeing and became more daring and adventurous in our outings into vanilla settings culminating in a visit to a pub one evening and ignoring the strange looks from others.

September brought us into autumn. As work returned to normal for both of us we found ourselves becoming very busy and having very little time for each other. I did worry that the relationship might falter as we couldn't bring ourselves to move in together and so the month gave me plenty of time to pause and reflect.

As life calmed down in October we resumed spending weekends together. I was finding life was very natural with Anthea and as well as enjoying outings in a vanilla setting we resumed visiting the club where we had first met in London. The club visits led to meeting more crossdressers as our status meant they were more willing to speak to me. I always enjoyed these evenings as Anthea would dress for a night out and it was enjoyable seeing her fully dressed for the evening in an elegant cocktail or evening dress and escorting her for the evening. We also received a couple of invitations to social events at people's houses and whilst some of them resulted in sex between participants, Anthea and I were happy to confine our passions to each other.

In November we wanted a repeat of the nice holiday earlier in the year and booked to visit Edinburgh for a long weekend towards the end of the month. Anthea had started buying more daywear and clothing suited to autumn. I liked the way she looked in autumnal-coloured knitwear, over-the-knee skirts and knee-high boots. She was dressed like this as we caught the train to Edinburgh and Anthea's confidence in a vanilla setting shone through in the confines of a railway carriage for four hours. In Edinburgh we enjoyed sightseeing during the day, holding hands as we toured the city on an open-topped bus, wrapped up in the cold winter sunshine.

We headed to a Christmas market in the city centre one evening. Anthea wore a thick coat over a deep red dress with thick tights and high-heeled ankle-high boots. She wore earrings and had makeup and had a slightly longer wig, with her hair over one shoulder. She looked gorgeous. In the market I enjoyed touching Anthea, putting my arm around her or holding her hand and generally watching her. Back at the hotel, I knew I couldn't hold back my passion and once we were inside our room I pressed Anthea up against the wall to kiss her. I unfastened her coat and admired the view before removing it and then turning her around to give me access to her bumhole. I moved her pants to one side allowing me to slide my cock inside her. I pressed her against the wall as I fucked her, slamming my cock deep inside her and fucking her roughly. Anthea loved it and was gasping with each thrust. My climax wasn't long in coming and I released my load deep into her. Exhausted, afterwards, I sat down on the end of the bed watching, with pleasure as my cum started to leak out of her and the white cream contrasted against the darkness of her black stockings and as Anthea felt the sensation of it she giggled.

As December came to a close I reflected on my year with Anthea and what the future held. Anthea and I had always agreed I shouldn't see her in male mode and we had managed to achieve this despite a few close shaves during our time together. We both knew it would shatter the illusion if I saw her as a man and she still had to spend most of her life like this as she needed to for work and to spend time with her family. Anthea was thinking about the future too and despite the progress she had made in spending more time as Anthea in vanilla settings she wasn't ready to make the leap to transitioning just yet.

As the New Year approached we sadly but amicably agreed to split up. As midnight approached at a New Year's Eve party I pulled Anthea in for one last kiss and cuddle before we said our goodbyes. We had no idea what the next year would bring but we had both seen the opportunities we wanted to explore further in the future.