My neighbor and I knew each other practically since forever. We grew up with each other. We hung out a lot. We went on adventures together. We were neighbors, best friends and everything else you can be without being in love with each other.

Yes, my best friend was a girl. Later on she was a woman. But she wasn’t one of those that was into girl things. She all the time hung out with us, with the boys. She competed against us in sports, she was the one jumping off the highest trees over at the lake, she was the one calling the shots. I liked her. And she liked me.

We all the time, from the age you are interested into such things, had partners. We had lovers, we had our long time relationships up and running, we had our broken hearts and in the end my neighbor was all the time there for me. And I was all the time there for her. We were nothing but best friends forever.

Our partners all the time knew about the two of us. Everyone in town knew of us. They were talking behind our backs from time to time. The told us to begin dating each other. We declined. We didn’t wanted to ruin the friendship we had up and running. It had more value for the two of us.

But a few years ago it hit us hard. We both were twenty eight years old back then. My best friend and I we got through a messy breakup in the same moment of time. Luckily we still had each other. We began to hang out a lot. We listened to each other. We tried to built up the other one again. And we shared more than just one drink from time to time.

So one Saturday afternoon we were hanging out at her place. She had moved back into her childhood home after her breakup. Her parents were traveling the world for about two years. So instead looking for a place of her own after splitting up with her boyfriend she occupied her family home. It was convenient, it saved rent and someone had to look after the place she probably would own later in her life. And yes, while hanging out, we did some day drinking.

We were kinda tipsy when she came up with a great idea: “How about dressing up a little bit? Taking a few pictures of us while pretending to be someone else?”

I shrugged my shoulders: “Why not. I am in.”

By the looks of it she already had a plan as what we should dress up: “How about you turning into a woman while I turn into a man?”

As if she wasn’t running around in men’s clothes always. But well, why not. It was a distraction from my broken heart. And I have to admit, the wondered of dressing up as a women had something arousing.

So we went upstairs. Into her parent’s bedroom. Looking for some fitting clothes. Luckily we found a lot. Her mom has left the bigger part of her wardrobe back at home. So did her father. It took us some time to pick the right, some fitting ones. Luckily for me her mom was relatively tall and chubby. So it looked good. I haven’t got the most masculine frame on Earth, but well, I think you get what I am trying to tell you.

Each one of us picked a full set: She got some jeans, a flannel shirt, some boxers, so she chose pretty much the same attire she was wearing always. I went into a different direction. I choose some sexy, slutty clothes: Short skirt, the most lingerie like underwear I found, some stockings, and a very deep cut shirt. Because when dressing up female, then I’d do it the right way.

My best friend smiled when she saw my choices. Then she began to undress herself. No, she wasn’t leaving the room. She just stripped naked and put on the new clothes. She signaled me to do the same. I struggled to pull blank in front of her. It put a smile on her face: “Come on. As if you never have gotten undressed in front of someone else before.”

She had a definitely had a point there. So I began to undress. I got totally naked. I set my boner free. Yes, seeing my best friend naked gave me a raging hard one. She, the reason for my erection, noticed it and commented on it: “Have I done that to you or are you just excited to wear some female clothes?”

I decided to go down the honest path. I told her that it was both. A gigantic smile appeared on her face when she heard what I was saying: “Good. Now hurry up, get dressed.”

Luckily the cloths somewhat fit: The underwear, the lingerie worked out great. It wasn’t covering my boner, but well, it wasn’t designed to do something like that. The pantyhose was stretchy enough. The shirt was a really tight fit and you could see parts of my belly. But well, you can call that sexy. And the skirt, it covered everything. At least when I was standing up straight.

Once I was done, I placed myself in front of a mirror. And I must admit id had something. And the smile on my best friends face told me that she liked it too. Even more, she practically was undressing me with her eyes. A never ever had seen her doing something like that before.

Then we went back downstairs. We took our phones and began to take pictures of us. We fooled around a lot. We tried some official looking ones, we tried funny ones and we tried sexy ones. It was during the sexy ones that she whispered something into my ears: “Seeing you dressed up like a woman made me soaking my boxers.”

A gigantic smile appeared on my face. I just asked her the following: “So you wanna get fucked by a woman too?”

She shock her head: “To be honest, I want to fuck the woman.”

It took me some time to process her answer. I had to think about her proposal. In the end, I said yes. I told her that she can fuck me if she wants too. A damn fucking gigantic smile appeared on her face. Then she left the room. She went upstairs. She told me that she would be back soon: “Okay, I am waiting for you.”

Then I sat down on the sofa. I spread my legs, totally ignoring the fact that I was wearing a short skirt and relaxed for some time. Counting the leaves on a pot plant on the opposite side of the room. To kill the time until her return.

When she came back she looked different. It took me few moments to understand what it was. She was wearing a bag in one of her hands, but that wasn’t the thing that was catching my attention. I checked her out from tip to toe. It took me more than just a few moments to figure it out: There now was a bulge between her legs too.

I had to stare between her legs. She noticed my behavior. She probably enjoyed the attention I gave her. But instead of thanking me, or being nice to me, she called me out for how I was sitting: “Don’t sit there like a pervert. Don’t sit like a man. Cross your legs. No one wants to see your half hard dick.”

A shiver went through my body when I heard her commanding voice. I immediately complied. I crossed my legs. I was sitting like a woman now. A smile appeared on her face when she saw what I was doing. Then she sat down next to me. Not really knowing what to do next. And I had no clue either.

We both were turned on by each other. But we both were more than just nervous too. We might have checked each other out in the past, but nothing sexual ever came out of it. We really liked each other, we really got along with each other but turning it all into a sexual thing, we both were not so sure about the fact if it was the right thing to do.

The mood turned from sexy and playful towards awkward. Very awkward. We both probably wanted to leave. She was the first one attempting it. She stood up and was on the verge of walking away when I grabbed her hand. With a firm grip. I held her back. I stopped her from walking away.

Then she turned around. We looked each other in the eyes. Something connected. Something made boom in our heads. A warm and fuzzy feeling showed up in our bellies. She froze. I froze.

Some time later, I honestly can not give you a more exact description, we slowly moved closer to each other. While still looking each other in the eyes. Then our lips were touching. We shared our first shy and very gentle kiss. It felt good. It felt right. The first kiss was followed by a second one. Then a third one.

Meanwhile we were hugging each other. Being that close to each other felt nothing but good. Even better, it felt fucking awesome. We still were kissing. The gentle kisses soon turned into passionate ones. Our hands began to wander all over our bodies.

Now we both knew that we were doing the right thing. It just had the right feeling to it. Or in other words: It was mind blowing kissing her. Holding her in my arms. It felt in about the same for her. And yes, we both were really turned on again. Horny was in full swing.

She unzipped her panties. A decent sized plastic dick was hidden beneath her boxer shirts. She told me to suck on it. To lube it up well before it went up my ass. I complied. I took the toy as deep as I could. She even pressed my head onto it. In a very gentle way. Not by using brute force. It was not about hurting me, it was about showing me my place. Needless to say her doing was nothing but a turn on for me.

I lubed the toy up as good as could. I put as much of my saliva onto it as feasible. She called me a cock sucker. Her cock sucking slut. Hearing her saying something like that was nothing but a turn on for me. It made my hard on spitting out pre cum.

Then it was time to fuck. She told me to get on the sofa, on all of my four and to spread my ass cheeks as wide aside as I could. She totally ignored my balls and my dick. She was only interested in my fuck hole. And she knew what she was doing. She probably had done the same things with some ex boyfriend before.

At first she slid one of her fingers inside my dirty hole. It already felt good. She played around with me for some time. To make me get used to the feel of it. To open up my fuck hole for more.

Then she slid a second finger in. While using plenty of lube. Now I began to moan out loud. It felt so fucking good. I even asked her for more. Soon after my greedy asshole swallowed three of my fingers. She called me her dirty little slut.

Then, after cleaning her finger with some whet wipes she brought with her she pulled a condom over the strap on. Then she lubed him up. And gently slid that thing up my ass. She clearly was in no hurry. Neither was I.

The moment the toy penetrated my fuck hole moaning escaped my throat. The toy sliding inside me felt so good. Again, she took her time. She gave me time to adjust to the feeling. While spanking my ass. And calling me a naughty slut. Yes, my dick meanwhile was leaking pre cum.

Once I was used to the feeling, yes she asked me, she fucked me. Gentle, but as deep as feasible. My eyes began to run in circles. Saliva was dripping out of my open mouth. I lost it. She turned me into her mindless fuck toy. The only thing I did was telling her to go faster, and harder. And yes, she complied.

Now my moaning was filling the room while my pre cum was messing up the sofa I was kneeling on. My meanwhile limp dick, my still hard and filled balls were bouncing back and forth with every thrust she gave me. She fucked me so damn fucking good.

I have no clue how long she was fucking the shit of me. Suddenly some inner heat was building up. Sweat was running down my body. Something was definitely happening with me. Something was building up inside me.

She kept on going. She knew how to proper fuck a men. She called me her bitch while giving me one hard and deep thrust after the other. She clearly enjoyed herself. Then she gave me one really hard, one really deep thrust and boom, I came. My balls were unloading themselves.

It was my first orgasm from anal only. It felt incredible. My hole body was trembling. Now I was really gone. I collapsed onto the sofa. She gentle pulled out the toy. Then she gave me a few gentle kisses on my neck while whispering something into my ear: “You are my good boy now.”

That evening my best friend turned into my girlfriend. It was the begin of the best relationship I ever had. We still are a loving, caring but very kinky couple. For the bigger part she is the man in our relationship, and I am the woman. Not just in bed, but everywhere. We even stopped pretending to be typical, average when we are with other people. We accepted ourselves. And we are more than just happy now.