Before I get into the actual experience, I’ll give you some backstory on how we got there.
Growing up, I had a best friend named Brian who was also my neighbor. We met when we were 5 or 6 and both also ended up having older brothers who became friends through sports. So basically, we were together all the time, whether it was hanging out together at one of our houses or at sporting events, either our brothers’ or our own. We were essentially inseparable.
Brian’s brother was an exceptional hockey player, and even though we all played in some capacity growing up, he was miles better than anybody else in the leagues. Because of that, Brian and his family moved away when we were both 11 years old so he could pursue sports. It was tough when he moved but we still stayed in contact somewhat. This is a few years ago now so social media was still relatively new. We became friends on the various platforms and stayed in contact that way but eventually lost most contact when we entered high school aside from the occasional post updates.
When I was in 10th grade, I noticed Brian’s posts becoming much more feminine. As kids, Brian was always really interested in playing with action figures but also dolls which he had a ton of for some reason. Or if we were playing some sort of make believe game, he would always want to be the princess or queen, etc. It’s not really something you think of as a kid but when he started making his transition it all started to make more sense.
Anyways, like I said, his posts became much more feminine and I noticed he was started to post himself in women’s clothes and everything else. Fortunately, Brian’s family was extremely accepting so I’m sure that helped with his transition tremendously which is great. So I guess you can say he started to transition in about 9th/10th grade.
It wasn’t until 12th grade that he started going by his new name, Joelle, which I assume was a play on his middle name, Joel. Joelle even created a new social media account which she friended me on, and I accepted, knowing who it was. Aside from some happy birthdays and casual conversations, we never stayed in too close contact and I never brought up the subject with Joelle about her transitioning until she was back in town my senior year of college.
I was home on spring break and I guess that Joelle’s family was also in town, visiting some old friends, my parents included. Being that I’d stayed in some contact with her, I can’t deny that Joelle was an attractive trans woman. She was 5’ 6” tall, about 145 pounds but fit, and her parents had even funded her breast augmentation surgery in college. She’d upgraded to about a C- cup but they definitely couldn’t have been cheap because they appeared to be very well done. Since she transitioned a few years prior, she had truly transformed in looks completely and if you wouldn’t have known prior, you would’ve never guessed Joelle used to be Brian aside from the semi-masculine features that are hard to hide, such as muscle tone and jaw lines, etc. I never found myself sexually attracted to Joelle until I finally saw her in person when she came back to visit with her parents…
“Hey James!! It’s been so long!!” She said joyfully as they walked into my parents house. She threw her arms around me like we’d stayed in close contact all of these years which surprised me.
“Uhh hey! Nice to see you again!” I said somewhat awkwardly, not expecting such an energetic greeting.
Joelle was wearing a tight fitting white crop top shirt which exposed her belly button and was just loose enough that her breasts caused the shirt to stick out from her stomach about an inch or so. She had on tight jeans and her hair was brown and about shoulder length. When she backed away from the hug, my eyes quickly flashed down at her crotch region out of curiousity. I didn’t see any sign of a bulge and considering how tight her jeans were I thought she may have been post-op. When I looked back up to meet her eyes, I saw her smiling, guessing that she must’ve seen me look down. I awkwardly smiled back and blushed some out of embarrassment but her smile made it seem like she didn’t mind.
Her family had been planning to come over for dinner so we all sat down and enjoyed each other’s company for about an hour and a half or so. Joelle sat next to me at the table and it honestly felt like we’d stayed close all of these years. We talked about school and sports and all of the stuff we used to talk about without really missing a beat. Nothing had changed at all personality wise and I really shouldn’t have thought that it would’ve. Joelle was the same person I knew as a kid and it felt amazing getting to talk to her again.
Being that Joelle and her family were visiting from out of town, my family had offered for them to stay at our house for the night.
“James, we figured that Joelle could just stay in your room tonight since we’ve turned your brothers room into an office and it would be more comfortable than the couch. We can just use the air mattress on the floor for her to sleep on,” my Dad told me.
This news caught me by surprise but it’s not like I could say no. Besides, it seemed like our parents had already thought this out without telling us anyway. When my dad said Joelle could stay in my room I caught a slight smile from her, telling me that she was intrigued by the thought of staying in my room. What really caught me by surprise was when we were all about to get up from the table and her hand brushed up my thigh.
“Oh I’m sorry! I didn’t realize your leg was there!” She said as she continued to stand up, looking back at me and winking.
This totally caught me by surprise. I mean, we had been getting along and talking like we hadn’t missed a beat but was there some sort of attraction I was missing? I was still very confused about the whole situation because I did think Joelle was really attractive but had never been attracted to a trans woman before. My mind was racing with all kinds of possibilities as I stood up to help clean up after dinner.
After dinner, our families hung out on the deck for a while and talked some more before we all started to turn in for the night. Joelle and I headed towards my room together. She was walking slightly in front of me and I couldn’t help but look at her ass in her tight jeans. It was shaped beautifully, cupped nicely by her jeans and swaying side to side as she walked. It was obviously firm but not overly large, really fit her body well.
I must’ve been looking too long because as we approached my room, she slowed down and I nearly ran into her.
“Did you forget what room was yours?” She said teasingly.
I laughed it off and hoped she didn’t realize that I’d been looking. I opened the door and we both walked in and laid down on our beds, mine my normal bed and Joelle on the air mattress.
“Finally a little time to ourselves!” Joelle said as she sprawled herself out on the air mattress. “I was getting tired of listening to our parents talk about the same old stuff over and over.”
“Yeah I hear you,” I said, agreeing. “I’m gonna change into something more comfortable. Do you need a pair of shorts or anything or did you bring some stuff?”
“No I brought some,” Joelle said. She reached under my bed and grabbed her bag. “I dropped it off in here earlier!”
I went into the bathroom and changed quickly. I came back out to see that Joelle was also changing and was just about finished. She had put on a larger white T-shirt which fit much looser but was cut short again, exposing her lower back and stomach. I could tell she had removed her bra because it was laying on the floor next to the air mattress. She was pulling up a pair of short shorts and I saw that she was wearing a thong before her shorts were all the way up. I could also see a bit of her bulge now that she had changed into some less restrictive clothing.
*am I really this attracted to her? She is so damn sexy. I’ve never felt this way before but I can’t deny the attraction*
“Oh, sorry I didn’t think you’d be coming out so quickly!” Joelle said as she turned around, brushing her hair behind her ear. “I hope you don’t mind!”
“Nope not at all!” I said. “You know you’re always welcome here to do whatever! We’ve known each other our whole lives.”
Joelle smiled and thanked me for always being understanding. She could tell that I was trying to hide my awkwardness but it must not have been going very well. We were still getting along great but there was an obvious tension that I think we both noticed.
We both laid on our beds and continued talking for a while before I finally broke the tension, hoping to make it less awkward for both of us.
“Joelle, I’m sorry we lost touch the way that we did, especially when you started transitioning. I want you to know that had nothing to do with our falling apart, I was really happy to see that you had a good support system around you, but I should’ve made more of an effort to keep in better touch.”
“You don’t have to apologize! I know that’s not why, it’s just because we were so far away, it’s not like we could’ve avoided it completely.” Joelle said.
There was a bit of a silence before Joelle spoke next.
“Sooooo, is there anything else you want to ask about my whole transition? I can tell you’ve been a little bit awkward since I got here,” Joelle joked in a light hearted way.
I laughed as well, happy to know she wasn’t upset that I was a little bit awkward and tense.
“Yeah I guess I’ve got a few questions,” I responded, laughing slightly. “How does it effect your sexuality? Like do you consider yourself gay or straight still or what?”
I knew that was a little bit straightforward of a question but Joelle answered it quickly.
“I consider myself gay for sure but slightly curious. I’m mainly attracted to guys but I’ve actually had a couple sexual interactions with my more adventurous girlfriends. So I guess I’m bisexual if you really break it down.”
“I’ve gotta be honest, Joelle. If I didn’t know you were trans I wouldn’t even second guess it. You’re drop dead gorgeous,” I say.
Joelle smiles and blushes, brushing her hair back from her face and behind her ear. “Okay, my turn,” she says. “What about you, how’s your sex life been?”
The question slightly caught me off guard but I figured I’d answer honestly since she did for mine. “It’s been pretty good! Nothing too crazy, a couple friends that I’ve fooled around with but nothing too serious since I’m still in school and all.”
“No experiments with your guy friends?” Joelle asks.
I laugh, “No not up to this point! I mean living with a bunch of guys in a house, you see your fair share of dicks walking around the house but I’ve never had any drunken nights where something has happened.”
I look down to see Joelle lying on her back with her hands above her head, causing her shirt to ride up her stomach to just below the bottom of her breasts, revealing her tight stomach.
*damn she really has a great body*
“Alright, my turn again,” I say. “What do you like more, having sex with guys or girls?”
“Well, I guess it just depends on my mood! I definitely have sex with more guys than girls so I guess them. It’s just different. Like women are much more sensual usually and you can tell when they’re enjoying it but sometimes you have to wonder because there aren’t as many physical cues. But when I fuck a guy, you can tell he likes it if his cock is rock hard, and they’re a little rougher which I like more I think. So I guess guys!” Joelle explains.
“Do you consider yourself a top or bottom?” I ask out of curiosity.
“I’m vers. Usually if their cock is bigger I bottom because I just love that but if I’m bigger then I usually top. But you also have guys sometimes with huge cocks who are super submissive so it all depends! I actually had sex with a guy recently who no joke had a 10.5” dick but all he wanted to do was sub to me. It was different for sure, had to hold on with both hands!” Joelle said, mimicking herself fucking a guy while holding his cock with both hands.
I really start to get turned on to the thought of Joelle having sex with another guy and begin to wonder what it’s like to have sex with her. My cock starts to grow slightly in my shorts.
“Okay my turn,” Joelle says. “Have you ever thought of having sex with a trans person?”
I get the feeling that the questions are beginning to lead us to the inevitable hooking up.
“Uhhh, not really until recently! The more you talk about it the more fun it sounds!” I explain.
I look to see Joelle sitting cross legged on her mattress facing me, her arms above her head, stretching. Her shirt has risen up slightly more, revealing the bottom of her breasts. I can see her surgery scar but only slightly. I must’ve been looking too long because when I look back to Joelle her eyes are locked on me and she’s smiling.
“You know, I’ve caught you looking like 6 or 7 times tonight, do you just want to see them?” Joelle asks.
Before I can answer she begins removing her shirt slowly, revealing her breasts in the dimly lit room. Whoever did her surgery was great because aside from the slightly visible scar, they barely look fake. They appear supple and are perfectly even, somewhere in the C cup range. They fit perfectly above her fit stomach. I feel my cock continuing to harden in my pants and reach down to adjust myself before it pokes out somewhere unexpectedly.
Joelle notices me shifting and takes that as a sign that I’m interested. She slowly stands up and begins to walk towards me, her shirt laying behind her on the mattress.
*is this really about to happen?* I wonder
Joelle continues to walk towards the bed and eventually crawls on top of me, her brown hair hanging over my face. She can tell that I’m nervous as I haven’t moved much or made any moves, mainly because I’m not sure what to make of this quickly moving situation.
“Just go with the flow. If I do anything that you’re not comfortable with, just tell me to stop…” Joelle says as her hands begin riding up underneath of my shirt, begging me to take it off. I lean forward and kiss Joelle deeply, immediately overcome with lust in the moment. We kiss for a few seconds before I sit up and take off my shirt.
Joelle quickly takes control and straddles me in the sitting position as we continue to make out. Her legs are wrapped around my waist and I can feel my cock getting harder and harder. Eventually I feel a bulge from Joelle and realize that she is also getting hard. This new feeling is overcoming me with new sensations as I wrap my arms around Joelle and kiss her deeply, our tongues darting in and out of each other’s mouths.
Eventually, Joelle pulls back and motions for me to lay on my back. I do and can see the pleased look on Joelle’s face as she sees my erection straining against my shorts. She grabs ahold of my shorts and pulls them down slowly until my cock springs out, hard as a rock for her. At full mast, my cock is 7.5” long, decent girth, and circumcised.
Joelle continues taking off my shorts and grabs ahold of my cock, her legs straddling me. “Are you okay?” She asks.
“I’m more than okay, this is amazing!” I respond.
“Then you’ll love this…” Joelle responds.
She grabs the base of my cock tightly and almost immediately deep throat’s my entire cock, in one swift motion. I feel her throat straining against my length as she continues to bob her head up and down deeply, sucking my cock with a ferocity I’ve never seen. I feel her spit draining out of her mouth onto my balls as she sucks until she finally eases up, slowly sucking the top of my cock as she jerks me at the same time.
I hear Joelle moan as she just really be enjoying sucking my cock. The vibration of the moan adds a new layer of sensation that is almost too much for me to handle. I look down to see that she has removed her shorts as well but I cannot see her cock from this angle. I begin to wonder how big she is and how hard she is, something I’ve never had to wonder about before.
Eventually Joelle begins to lighten up as she sucks the last of her spit off my cock and releases me from her grip.
“Want to take it a step further?” She asks, making sure I’m comfortable with what’s happening.
“I’m positive” I say, excited to see where this journey goes.
With that, Joelle spins around to present her ass to me in the doggystyle position. Her legs are slightly spread and I can see her balls hanging below her beautiful ass. I’m more turned on than I could’ve imagined.
I quickly get up and get behind Joelle.
“Wait a minute,” she says.
I worry for a split second before I see her hand reaching around to her ass, rubbing saliva onto her asshole for lubrication before sticking two fingers in as a warm up, I guess.
She removes her fingers which I take as a sign to move forward. I rub the top of my cock to get some precum for added lube.
I prod my cock against Joelle’s asshoke and begin to apply some pressure. I feel her tight asshole loosen slightly and see that the head of my cock is halfway in. I hear Joelle moan as her asshole loosens more, accepting my cock. Suddenly it releases further and I thrust my cock into her ass completely, filling her with my manhood.
Joelle moans deeply as I being thrusting in and out of her. I had never had anal sex before and it was a whole new experience for me. As I begin to thrust harder I feel Joelle pushing back, begging me to go deeper and deeper. My balls as clapping against hers as we rock back and forth, both of us fucking each other in harmony. I see Joelle reach a hand underneath of her and I assume it is to stroke her own cock.
*Should I be doing that for her?* I wonder.
Suddenly Joelle sits upright as I continue to fuck her. She brings her left hand up to caress my face as I turn towards her to kiss her.
I reach around Joelle and run my hand down her stomach until I finally reach the base of her cock. I stop thrusting for a moment as I grab ahold of her cock, the first one I’ve ever held other than my own. It fits my hand fully but not overly large and rock hard. I begin stroking her and imagine she is about 6 or so inches big. Joelle moans again in pleasure as she enjoys the feeling of my cock in her ass as I stroke her.
Suddenly she bends down again and pulls away from my cock, releasing me from her ass for a moment. I wonder if I had done something wrong before I see her turn onto her back, he legs spread, awaiting me to enter her in missionary position.
I take action and quickly get on top of Joelle, sticking my cock back into her slightly gaped asshole. I begin thrusting again, this time seeing her cock and balls flop with each thrust. I take hold of her cock again as I fuck her, stroking in rhythm as best I can. I feel her asshole tightening around my cock, hinting to me that she is really enjoying this rhythm we developed. Her cock is magnificent, and her tits are bouncing with each thrust of my cock.
I fuck her quicker and quicker until I get the familiar feeling that I am going to cum soon.
“Oh fuck I’m about to cum!” I say.
I keep thrusting when I hear Joelle say, “yes, yes! Cum on my tits!”
Her begging sends me over the top as I pull out my cock and unload ropes of cum all over Joelle’s tits, covering them as well as her stomach and even a some on her face. I continue jerking my cock as the sensation fades, eventually slowing down as I feel my cock begin to slightly soften. Joelle and I are both breathing hard as I look down to see her cock is still erect.
*I can’t just leave her hanging* I think to myself.
I make the decision that I’m going to blow Joelle. I had never done anything like that before but in the moment, it just felt right. I love my head to just above her cock and grab ahold of the base before sticking out my tongue to caress her dick. I look up to see Joelle looking down at me, her face pleading me to go further. I turn my attention back to her cock and take in as much as I can while also trying to jerk her. It takes me a few bobs if the head to get the rhythm down. I can’t go nearly as far as Joelle but I am able to get 2-3” in and feel that is pretty good for the first time.
I keep sucking Joelle as I hear her moan and she reaches her hands down to grab my head, hinting to me that I must be down okay. After a couple minutes I remember Joelle saying that she liked having a cock in her ass, so I do the next best thing and reach below her balls and stick two fingers in her ass, hoping this would send her over the top.
I must’ve been right because shortly after I hear her moans increase and breathing speed up. I curl my fingers inside of her asshole for a new sensation and I hear Joelle say, “Don’t stop! Don’t stop!”
Suddenly my mouth begins filling with a warmness that I determine must be cum. I release her cock from my mouth and continue stroking her, seeing her cum shoot high and arcing back onto her stomach. I keep stroking until Joelle slows her breathing down, signaling to me that her orgasm is completed.
I realize I still have some cum in my mouth and swallow it, unsure of what else to do. I let go of Joelle’s cock and stand there awkwardly, trying to make sense of everything that just happened.
“James…that was fucking amazing!” Joelle says.
I’m happy that she broke the tension as I was unsure of what to do next.
“That was definitely a new experience for me,” I respond, “but an amazing one. I really don’t even know what to put into words right now.”
“Do you…want a towel or something?” I offer.
Joelle laughs and agrees that she needs one. When I return with the towel, she cleans herself off and lays down on my bed. I lay down beside her in hopes that we can talk some more about what just happened.
“Next time, I want to be inside of you…” Joelle says somewhat unexpectedly and suddenly.
I feel my cock start to harden in my shorts again……