[TM] first I’m time with a man while being a woman.

This was one of the best days of my life. I’m mean I’ve had a few good days so it would be insulting to say it was flat out the best day ever. But I’m sure we can all relate to that part. First let me give you a bit of an insight as to the beginnings of this predestination.

By the age of 16 I was proficient in the use of girls clothing to create the overwhelming sense of ease and joy in being feminine. The rush of the moment and the sexual urge has no doubt been the catalyst to my addiction. Addiction isn’t a good word but it’s as close to explaining the fact that it became an inevitable urge that I could not suppress. I suppose like hunger, and hunger isn’t an addiction. Sure I went long periods where I never had the urge but I’d always find that little need in the back head to fulfil my femininity. At aged 21 I had a small collection of random outfits and under-ware and was developing my skill sets which included tucking and creating cleavage. Now this was enough to look down and be contended that I look feminine enough. This was short lived. If I ever went a period where I’d sustain my urges, they would come back with new ideas to try something else. Now by that I mean add another step in the process that makes me more feminine and for a while I’d be contented. For example I’d buy heels. Then I’d try sexy lingerie, dresses, skinny jeans, all sorts of toys of ever varied colours and sizes.

I then had scare with my girlfriend finding some underwear that wasn’t hers in my drawer. I managed to convince her it wasn’t another girls. Which luckily was her main concern. I suppressed it the best I could but the urges never went. I just had to be more careful and possibly the main reason I progress so slowly. Id learned that this silly thing wasn’t important enough to upset the people I loved. So why tell them. Keep it a secret and do it as little as possible. I class myself as a straight guy so I was always ashamed of my secret. I could never actually admit that I am probably every bit as bisexual and well whatever I am on the scale of the gender/sexuality spectrum other than a Heterosexual male. It’s been a slow process pushing my boundaries with what I can get away with and still feel comfortable with.

To get an idea of how slow a process it’s been. Yeah I’m a wimp and should have bitten the bullet years ago. I never got a a wig till I was in my 30s and never tried makeup til a few years later. But when I did the switch clicked. I was looking at the reflection of the girl that I have always wanted to be. I could see Eva and even though I did not look perfect I could see the the potential that I might just pass enough to be a girl and live my dream.

So i have an ever growing collection of beautiful clothes. Makeup. Wigs. Shoes. All the ingredients to make a pretty girl. But I’m not content. I could have better clothes. Better skin. Better makeup. It’s not an easy process believe me. I have to shave. Fake tan. do eyebrows. Nails. Then we add jewellery and bags. By now you can tell I’m not messing around. I’m 33 years old and have more stuff than a teenage girl. When I’m dressed I feel a million bucks. Im not going to say I look amazing cos I don’t. But I look good enough that I feel amazing. Finally I’m at the position where I can live out my desires to experiment with life as a woman. By that I mean push the next boundary of my desire to be a woman. Going out. Showing people me. Judge their reactions to see if i am actually passable or my feelings cloud my judgement of my looks. It’s complicated to explain unless you are in a similar position as me but I think it’s hard to see how you really look from another persons perspective when you are so infatuated by the female you. I have digressed.

This digression is important. Hopefully now I don’t have to convince you that this actually happened, or put true story as a title. I suppose most girls-like me can relate to this and know I’m not full of….

I had a plan. Spend the night in an apartment in the city and be me. without any time constraints or fear of someone walking in the door would be bliss. I got an early check in and after some quick shopping of some more fake tan and rose wine I was exited at the thought of it. It takes me ages to get ready. It’s not a quick process remember I have not had years of practice like other girls my age. But I love the process. It’s great fun. I start with a shower and wash head to toe and cheek to ….. I’m clean ok. I shave. I’m not naturally hairy but nothing worse than a hint of shadow and you gotta have the smoothest legs. Bit of fake tan then stick on some underwear and a long top while i do my makeup. Why did I never do makeup earlier. It so clever. The tricks and tips you learn, its an art form. Brows, Eyes, contour, foundation, lips and finally lashes. A bottle of rosé later and Im ready for my hair. But we still have nails to do. So another half bottle and I’m chilling in full fem doing my nails, watching Ariana grande playlist on the tv. Life is good. I pick out my outfit. Nothing too fancy just some ripped black skinny jeans. Sorry, I’ll start with the, tightly tucked in black panties, Black bra with a burnt orange oversized knitted top. As I say nothing to flash. But casual and cute. I put on some trainers and and a Barbour jacket. And decide to go for a stroll round the city. I’m a country girl so it’s a novelty to be able to walk out and have pavement on my doorstep. I go to the shop and buy some Bobby pins. My hair always lands in my face. Self service of course. Then make my way round a short walk. I fancied a cigarette. I don’t even smoke. But I thought it would be fun. I walk into the corner shop and for the first time used my very best ( read bad ) girls voice to get cigarettes. Ok so now I’m pushing a new envelope here. But I’m smitten. And tipsy. I wander some more and admiring my reflection in the shop windows and disguise my male swagger as much as I could. I must have been doing something right. As I walk past one guy he mutters “how you doing” as he passes. Mission accomplished. I make my way back to the apartment after stopping off to take some selfies with some graffiti as a back drop.

It was cold and nice to get back inside. The place was a bomb site with clothes and makeup everywhere. I forgot to previously mention that in between getting ready I was messaging a few guys I talked to on grinder. After a few live pics and some dick pics in return I had narrowed down the candidates to a guy who sent a face pic that looked handsome enough. Now I may go off at at a tangent again but the juicy bit is on the horizon so stay with me. I’m not into men. I like men. I like the thought of being with a man. I think it’s sexy when guys fuck girls. Most importantly I get turned on by dick and more importantly a huge sexual desire to be fucked by one. But not really into men. I can’t explain it but that’s the way it is. The closest analogy I can give you is I don’t like tomatoes. I like ketchup. I like tomato soup.but I don’t like tomatoes. This tomato seemed like it would be good for tomato soup. I put on some pizza I drink some more wine. I message the tomato. I don’t know his name to be honest. For the purpose of the story we will just call him Tom

I was tipsy, horny and could accommodate. This Was a no brainier. You get to learn who the chancers and dreamers are and I knew pretty quickly that Tom wasn’t messing about. I had time to prepare. After a few outfit changes and most importantly changing to my pink panties, a burnt pizza later I had an outfit change. Tom requested I wore the skirt as per my profile pic. I know it delays the story but I know you need to know. The outfit of choice was a black leather skater skirt and an animal print puffed sleeve crop top with a high neck. Bare legs and black heels and pretty purple toe nails. Since you are probably wondering what my nails were like they kind of faded to bright pink with glitter on the index finger nail. As pretty as I could achieve when made up with rings and bracelets.

I send Tom a pic and he is delighted. Well I mean he said I looked sexy and he really wanted to meet. I ask him to come round have to entertain my notion to suck dick. It’s just like the thought of it turns me on. Imagining myself making a guy so turned on that this girl is making him hard. Tom was keen. He wanted to return the favour but I explained I wasn’t confident and that I’d rather I wasn’t into topping. I explained I wasn’t sure id go through with fucking but will see how I feel. I never told him it was my first time but mentioned I’d never met anyone like this. He understood that I just wanted to be treated like a girl. This understanding gave me some confidence Tom wasn’t a wanker.

So I bite the bullet. I think fuck It and hit send location. He probably won’t show I say to myself as justification for my irrational behaviour. I ask him how long he will be and he’s already left. Oh. The odds he’s going to show have just rapidly improved. And the place is a mess. I quickly shove my bits and bobs in the cupboard and freshen my lipstick, brush my teeth pre lube and pre pare my… what? I’m nervous but excited and feeling good. I was prepared and looked hot. Confidence is key right.?

I must be onto bottle number two but over the duration of the afternoon, I’m at a nice tipsy state. I top up my glass again and check the status on grinder. “What’s the number?” “1”. This is getting real. So I sip some more wine with etiquette. Like I say confidence is key.

The buzzer goes. I take a breath check myself in the mirror, then let him in. As I peak round the door I smile an squeeze out my most feminine “hi” I could muster and smile. He smiles back. It was cold outside. He was jacketed up with a hat and scarf. As I close the door behind him he un wraps his scarf as he stairs at me. I remember him saying “wow. Wow. Wow Eva you look really good”. He is the first person to say my name. Which was the first of many novelties. I keep smiling. A nervous smile perhaps but when he was smiling at me and complimenting me I couldn’t help it.

I make my way through to the living room sofa and he continues to rip of his hat and jacket as his gawking eyes lead after me to the sofa. He probably said wow you look good again. It was all I can really remember him saying. I perch on the sofa very lady like and take another sip of wine and offer him some. He declined. So I sit back and slightly awkwardly sit snug to him. His hand wanders over to me and almost as soon as I think what am I to do next he went in for a kiss. I hadn’t really considered this part but I didn’t have time to contemplate it. I was already delicately kissing his lips and getting drawn into it with the passion building between us. I remember feeling his stubble beard prickle my face and feeling his soft lips in the middle. It was an provocative feeling as it reminded me that I was kissing a guy. I could feel myself fluttering inside and I was getting really lost in the moment. I had to stop as my hair got stuck to his beard. I quickly fixed it from my face and stole another snog. This time my hand instinctively went to his crotch. I felt around to find his rock hard dick in his jeans. This filled me with more of that building feeling that I had inside. The thought that I was making him hard and it was for me is an amazing sensation.. I rub it through his jeans for a second until I fumble for his belt. I fumbled convincingly enough that he got the hint and pulled off his trousers for me. As I catch a glimpse of his dick I take a mental note of it and then start rubbing it gently with my hands. Picture my hands with rings and pretty nails gently rubbing his rock hard cock. Sitting side by side kissing each other.

Fine I won’t rob you of the details then. As dicks go it was nice. I’m not saying it was an omg that’s nice cock, more a , that’s not a bad cock kind of cock. I mean it was pretty average, far from small and most importantly not minging.

I refrained from kissing him and shuffled back slightly. I positioned myself so I could lean down and get his dick in my mouth. With one hand still on his dick I suck him off. I’m not sure for how long really. I was enjoying it. He was enjoying it. I was really enjoying it. I wanted fucked.

“Do you want to fuck me?” I said. “Yeah”he stuttered in a cute almost begging expression. I asked him if he had protection and he shook his head. His expression changed to one of almost sorrow. I think I rolled my eyes then go grab one from my bag. Told you I was prepared. I’d planned this for a long time and played it out in my head many, many times. His eyes followed me across the room then he followed me over like he was under my spell. I start to put it on him but only got it on a bit then gave up. I walked off to the bedroom as he put it on properly then made his way after me.

I got on the bed. Im not sure what I was thinking. Problem was I wasn’t. I mentioned the black skirt and pink panties so you are already aware that the access wasn’t an issue. I tried to like lift my hips back but my angles were all wrong and struggled to get him in properly. I think basically I then rolled on my side a bit near the side of the bed. Tom must of had a knee on the bed and the other on the floor. That worked. He slid in and even though he wasn’t that big. And I can do big. I could feel it right inside me, deep. He just fucked me slow and as deep as he could. Right to the hinge. He seemed to take joy in sliding it in as deep as he could. I could feel the full length work it’s way in as it bottomed out when his hips pushed into my ass cheeks. I think I moaned with every reciprocation. I just lay on my side leaning on one elbow and my knees slightly bent and together. I could look over my side and see him fucking me. Again I’m not sure how long this lasted. I was enjoying it too much.

Tom would fuck for a bit while I’d moan for a bit . I’d try move position and try get him where I wanted it. I found my self need to change position. Just because I wanted it more. I’m not sure how changing position could make it any better but I wanted it more. I kneeled on the bed head down pussy up and he was on his knees on the bed. At this point I was fucking him. Bouncing my butt into him. Much quicker than before. I could see myself in the full length mirror on the cupboard doors. I couldn’t believe it was happening. I just kept catching glimpses of us as we fucked. Some time passed and he started to mutter “I’m going to cum”. Torn between wanting to ease off and wanting to fuck him more I opted for the latter and let him pump me hard as he neared the orgasm I worked into his fucking motion too. I just remember going “ it feels sooo goood”when he shot his load inside me. I didn’t cum but man it felt good. That’s how I like it to be honest, cumming is over rated. I had leaked so much any way I was pretty much done. I was tingling and my whole body felt like it was suppressing an explosion. I just remember giving out little moans and curling up on the bed feeling soo fucking good, like a warm, full, cosy ecstasy feeling. I told him again how nice it was. Once I’d cooled down a bit and the feeling subsided I put my panties back on, we went back through to the living room. I sat down and had the rest of my glass of wine while Tom got his trousers back on. We both just smiled at each other then thanked each other as he put on his coat. We said bye and just like that,Tom was gone.

I can only liken it to my firs time with a girl. But as a girl and with a guy. It was insane. It was amazing. But felt I could do better. Like next time it will be better. See what I’ve got myself into.. it’s just added a new dynamic to the urge that I have to fulfil. I can’t wait. Xx

Source: reddit.com/r/gonewildstories/comments/lcj47a/tm_first_im_time_with_a_man_while_being_a_woman