Andrew was one of my FWB in high school. He was tall and athletic. Brown hair brown eyes. His cock was almost as long as Mark’s, white, thicker, and cut. His legs were hairy and so was his lower stomach. Not crazy and uncontrolled but manly and hott. A contrast from my smooth, soft, and slender body.

When Mark and I started to experiment in the stalls during basketball camp, we invited Andrew to keep watch for us in case he heard anyone coming. Eventually, he got curious too. Asking us what exactly we were doing and laughing in disbelief as we confessed. We convinced him to stand by the stall and look after his eyes adjusted to the darkness. Only a few minutes later, he traded places with Mark. My shorts and boxers were already around my ankles. Andrew asked me what to do. I grabbed his bulge in the darkness and gently squeezed. I told him when he gets hard, he can drop his pants and rub his cock between my cheeks. Initially I thought maybe he wasn’t interested. His cock soft and limp in my hand. I told him he could grab my ass. Then it shot up, almost instantly hard, trapped behind his shorts. I turned around and pressed my ass against his shorts. Feeling him grab my hips and my ass. Giving him a little preview and tease. Then I felt the warmth of his skin pressing against me. Andrew had dropped his pants and was now enthusiastically rubbing his cock against me.

Over the next four years, Andrew and I had many more opportunities than I did with Mark. Andrew and I were in baseball together and we had practice everyday after school. He would come over to my house to wait for his ride often. That meant regular two hour windows of opportunity. Since we were good friends, nobody thought twice about our sleepovers either. No idea I was on my knees giving him blowjobs or taking him doggy style at 2 in the morning. Our adventures filled with blowjobs, groping, quickies, and some role play to spice things up. I would do it in boy mode. In my baseball uniforms, basketball shorts, sweaty baggy workout clothes. And eventually we were able to dive deeper. I would often wear his older sister’s clothes. She was off in college and left behind a lot of clothes in her wardrobe. It started with a pair of panties. A quick swipe and hidden under his bed. Then our curiosity grew. I wore some skirts too. We built up to a full outfit when possible. Andrew often choosing what he wanted me to wear. And a few times lending me her lipstick that was left in her drawer. would do it in boy mode. In my baseball uniforms, basketball shorts, sweaty baggy workout clothes. And eventually we were able to dive deeper. I would often wear his older sister’s clothes. She was off in college and left behind a lot of clothes in her wardrobe. It started with a pair of panties. A quick swipe and hidden under his bed. Then our curiosity grew. I wore some skirts too. We built up to a full outfit when possible. Andrew often choosing what he wanted me to wear.

Andrew made me feel the most feminine. Anytime I was around him I couldn’t help but think about dropping to my knees and just sucking him off. He was gentle with me and kind. Always on my side at school and in practice. It felt like he cared about me in more ways than just being bros. Often times I would change after hanging out with him and my boxers were soaked in the front with my own precum. We wouldn’t even have to do anything sexual.

I had a threesome with Mark and Andrew. We planned that to be our last time together but Andrew and I had one more chance. His family had decided to move to a new house and he invited me over to his old one where he was staying until the next day when they brought the truck to load up his stuff. I was “going over to help him pack.” When I arrived, as soon as his door closed he embraced me. He wasted no time reaching into my shorts and grabbing two handfuls of my cheeks. I noticed that he wasted already hard. Poking against me. We made out at the door and he started to try and finger me when I pushed him away. I told him to wait and we both smiled real hard knowing what we were about to get into.

Upstairs every room was empty except his room. He had a lot of boxes filled already and the room was relatively empty. His bed remained and his television was still mounted. On his bed was a dress. Just by looking at it I knew it was going to be short enough to expose my ass if I bent over.

I walk over to the bed and ask, “Is this for me?”

Andrew replies, “Yeah. I was able to grab it before it was taken over to our new house.” He stands behind me grabbing my ass again. We tease each other with touching and dry humping for a few minutes. Then I excuse myself to his bathroom.

In my bag, I had a wig from party city. I used the previous Halloween as a cover to buy a wig. I bought two but I only used them when I was with Andrew or Mark. Then I would neatly store them in my box marked “Halloween” the rest of the time. There was a bra that belonged to a cousin of mine. I remember when I swiped it, I had to have it as soon as I saw it. Full lace and semi sheer. Andrew liked when I wore less revealing panties. He described it “like unwrapping a present.” So naturally my ex girlfriend’s boy shorts was lost and found in my collection of clothes to wear for Andrew. I had already prepped my body at home and I stood in front of the mirror examining all side of me. Smooth soft body. Wig on correctly. Dress cute and soft on my skin. Panties adjusted and bra in place. I felt so sexy. My brain was melted already and oozing out was a horny sissy. And to complete my transformation, I put on the lipstick Andrew had sitting on the sink for me. Deep red.

Our go to role play was for me to pretend to be his crush. I knew her in school. We had some classes together. Her name was “Ashley.” I can still hear him call me by her name when we were setting the mood. I Our go to role play was for me to pretend to be his crush. I knew her in school. We had some classes together. Her name was “Ashley.” I can still hear him call me by her name when we were setting the mood.

Andrew was laying on his bed. We had been having sex with some lights on. I had felt vulnerable at first but then it turned me on so much that he actually wanted to see my body. His fan light was on. I was in full view as I walked up to his bed to take his hand. I enjoyed kissing his neck and chest while he played with my ass. I marked his body with my lipstick on the way down to his boxers. I took my time. Knowing we would be all alone at the house and remembering it would possibly be our last time hooking up before we both went our separate ways in college. I gave him my most enthusiastic blow job. Even now I can remember his taste and how I was not shy to look up right into his eyes with half of his shaft in my throat.

I took him to the edge. Hearing him say, “oh fuck I’m about to cum.” I stopped and laid next to him on the bed. He turned me on my stomach and got on top of me. Andrew pulled up my dress and my panties down. Unwrapping a present like he wanted. Andrew spanked my ass. I could feel the jiggle vibrate up my back. Then his face was pressed all the way between my cheeks. I was caught off guard and let out a very feminine whimper. Andrew grabbed my hips to pull his face deeper. His tongue was pressed against my hole. It felt so incredible. I shook my ass on his face and he groped and spanked me. With the sting on my ass still burning, he put the first finger inside me. I was moaning uncontrollably as his knuckle went in and out of me. His kisses on my ass felt so sensual. Two fingers deep inside me I could feel my hole stretching. Almost ready to take the girth of his cock. Three fingers, I am being so loud moaning. Andrew doesn’t shush me. I know it’s okay for me to give in. He continues to lube my ass with his tongue. Then he goes for the record. 4 years of hooking up and we had never made it past the third finger. Tonight was the night to try. He knows my body. Going slow at first with three fingers. My eyes closed, head back. I’ve forgotten who I was and all I knew was that I was a girl named Ashley giving the guy who had a crush on her a chance at this point. And the fourth finger starts its way in. I push my hips up more to open my hole. One of his hands pulling a cheek to the side while I hold the other. Finally, the fourth one in. His thumb hooked on to my cheek. Gently and slowly he pushes in and out of me. Complimenting me and praising me the whole time. I’m so horny typing this out right now.

Then he’s on top of me. Cock sheathed between my cheeks. Kissing my neck and whispering naughty things about how good of a girl I’m being into my ear. I beg him to fuck me. I position myself in doggystyle on the edge of his bed. I’m directly under the fan light in his bedroom. Cheeks spread. Limp leaking cock dangling transformed into a swollen clit. Asshole now a delicate tight pussy awaiting Andrew’s cock. He pounded me. We made out while he was inside me. We tried every position possible with this last time we had. My favorite was reverse cowgirl. It felt good and I really liked looking back to see Andrew looking right at his cock going in and out of me.

I had a moment, as always, wondering what I was doing. Why was I doing it? We should just be packing up his things and maybe playing Xbox. Regular bros. That thought didn’t last long as I felt my clit stiffen up. We were in missionary. My legs wrapped around his torso. I grab my hard cock and began to stroke. Andrew watching me and continuing his rhythm in and out of me. I let go just a few seconds before I shot warm cum on myself. Andrew pushing it out the tip of my cock. He gently massages the tip for me and slows down his pace. But continues deep. Then his cock turns to steel inside me. A telltale sign that he was ready to cum. We make eye contact when I say, “cum inside me.” Andrew speeds up. Forgetting slow and sensual for my empty clit and focusing on pleasurable fuckdoll for his cock. And there’s not a single straight boy thought in my mind left. Only that I’m his crush named Ashley and he’s fucking my pussy.

Andrew cums inside me. My own cum sprayed out on my stomach and chest. He leans down and kisses me as he pulses inside me. We moan into each other’s mouths as our tongues twirl around one another. Then he gets up and goes to the bathroom. I lay there vibrating in every extremity. My toes. My fingers. My torso. My legs. My face. My swollen leaking clit. Andrew returns and kneels by my face. His cock is semi hard and gets harder as I suck it. My own clit begins to grow.

We didn’t have a round two. At the end of our 4 years together, we had our set hook up routine where I would suck his cock at the end just to clean it off and take any remaining cum in my mouth (it was my suggestion when I learned that I loved the taste of him). The remainder of the night we cuddled in bed and turned the lights off. He played with my ass more and I would caress his cock until we both fell asleep.

The next morning we quickly packed all of his things and I went home. It ended up being the last time we would ever hook up. We never reconnected in college or after. As far as I know we both still live in the same area and I’ve seen him only once or twice from a distance. Always too nervous to approach him. Andrew was my favorite lover of my two fwb. I never told him or Mark that. To this day, our last night together is on of my favorite memories to get me in the mood for dressing up and sissy activities. Majority of the videos I post I’m right in the middle of thinking about that night.