A Bloom in June Ch. 06

****This is Chapter 6 of an ongoing series about a middle aged guy having a fling with the 21 year old trans daughter of his college friends. As suggested, I have added in more context as to what came before so it can be read as a standalone, but, naturally it is best enjoyed after reading the previous five. ****

"Bro... Seriously... If some dude wanted to pay me a hundred bucks to chuck grapefruits at his dick I'd be sooooooo in." June said from under a blanket on my couch as I walked in the door after work.

"That was perhaps the greatest non sequitur I have ever heard in my entire life." I replied, closing the apartment door and dropping my bag.

"The book Sully!"

And with that she held up the copy of Rita Mae Brown's"Rubyfruit Jungle" to remind me. I had bought it for her because the septuagenarian college professor we met on New Years Eve recommended it to us after we brought her home so she could get herself off while watching us as we took turns fucking each other's asses.

Ok, maybe without more context that would be the greatest non sequitur of all time.

June is the nearly 22 year old trans daughter of two of my friends from my days as an Undergrad at Vanderbilt University. A few months prior to the above exchange, her dad had reached out to me to see if I would spend some time with her, because he knew I wouldn't judge her or make her feel uncomfortable.

What they didn't know is that June would end up finding me attractive and flirt with me, going so far as to drunkenly throw herself at me at a Halloween party. I rebuffed her on that occasion, but only because she was drunk. I was certainly attracted to her, despite the fact that I had never been with a trans woman before. It definitely wasn't over a lack of interest on my part. Just circumstances.

Eventually, after a lot more flirting we did hook up, and after some early puppy love from June we had settled into a friends-with-benefits situation. In the background of all of this was the drum beat of the 2024 US Presidential election. When the far right swept into total ascendency, June's dad ended his support for her self identity and demanded that she present herself to the world as male or else be cut off by them.

She understandably fled home, and has been crashing with me for the last two plus months. Over the course of that time we have fucked a lot, including a few times together with her best friend, Lizzie. Lizzie is the 22 year-old cis daughter of another set of my college friends, and she would be coming back to town in a few days when the semester began.

So while I was at the office for my first work day of 2025, June was home reading this novel that had been recommended - practically assigned - to her by Dr. Meredith Altman, a gender studies professor who had asked to watch us have sex on New Years Eve.

I ended up reading the book that weekend once June had finished it, and I saw why Dr. Altman thought it would resonate with her. Although I'm sure she recommended it more for the struggles of finding yourself when the world is targeting you for being different, rather than the part about a rich guy blowing his load when being pummeled by citrus fruit. But that part was certainly memorable and worth remarking on too.

I was looking forward to us resuming our play with Lizzie when she returned to campus, but June had other plans. I didn't see either of them for about 5 days as June spent all her days volunteering with two different non-profits aimed at helping trans people, while spending all her nights on campus with Lizzie.

Just when I was beginning to think I may never see her again I texted to ask about her plans for her upcoming birthday. She apologized for disappearing on me and said that she'd like to spend her 22nd with both me and Lizzie. So, I offered to either take them out for dinner or to cook at my place, eliciting a quick text response from her.

How bout we go out for dinner and then have desert at your crib?

sounds perfect to me! I responded.

---

As a middle aged guy my memory isn't quite what it used to be. That said, I remember January 11th of 2003 exceedingly well. Then in our late 20's, the boys and I spent the early afternoon drinking and bullshitting on Broadway in advance of our hometown Titans taking on Pittsburgh in a playoff game. Lizzie's dad was the only one of the group missing, but none of us gave him a hard time since he had a 14 week old daughter at home. The rest of us drunkenly trudged across the bridge to see what turned out to be a truly epic game.

You don't get to see a lot of overtime playoff wins in the NFL, let alone one where the winning field goal has to be kicked three times, so we were all very pumped when we left the stadium. It was actually June's dad, Jack, who suggested we head to campus to keep the party going by watching the old alma mater's basketball team play.

We arrived with only a few minutes left in the first half, and while the game wasn't as memorable as "The Music City Mulligan" was, it was still a good one. A one point victory over the #4 team in the country makes for a fantastic way to wrap up a hometown sports day for the ages. But what really helped to ensure that I remembered the whole day was that I was the only sober one after the basketball game ended, so when Lili called to tell Jack that she was going into early labor, I was the one who drove him to the hospital.

I was still there, helping to comfort Jack as he worried about Lili and the baby since she was only 6 months along at the time. Luckily he didn't have to worry for long, as just seconds before midnight mom and baby were both resting and fine. So I was there the night June was born, although a different name was initially on her birth certificate.

Just as it was the day she was born, January 11th was a chilly Saturday in 2025, but you would have never known it based on the outfits June and Lizzie were sporting when we headed out for dinner. June had on the shortest skirt I had ever seen her wear and no stockings. Over her silver sparkly skirt she sported a sleeveless flouncy black top with no bra beneath. Lizzie was wearing a black body suit with frilly edges along the neck as well as the arm and leg holes, which I only knew because the jeans she was wearing hung low enough to see at least two inches of the lace headed for her crotch.

The old man sported a black and grey button up flannel shirt, jeans and Jordan's. I was fully aware that I was the dud in the group fashion wise. Our unexpected fourth member was a girl named Lucy who was apparently close with Lizzie. She was also envisioned as some sort of gift for me as they thought they'd be able to get her interested in joining us in bed, but as it turned out their intentions exceeded their grasp.

At our first stop I opened a tab and grabbed myself a beer and three espresso martinis for the ladies. We toasted June's 22nd trip around the sun and then the three of them disappeared to the dance floor after quickly downing their drinks. After about an hour and two more drinks, I rounded them up for our 8 PM dinner reservation.

The three of them were quite giggly at dinner, but when it became clear that Lucy didn't want to come back to my apartment afterwards, they stopped dropping hints. After we finished up eating and bid her a good night, June told me that she was a gold star lesbian who had confessed to being interested in trying sex with a man at least once before graduation, but I apparently didn't cut the mustard for her college experimentation.

Not that I minded, since I was already looking forward to an evening with both June and Lizzie again. They each took one of my arms and we walked briskly back toward my apartment through the very chilly night.

I was getting used to the sideways glances I sometimes got when I walked into the lobby of my building with June. On this evening, however, it went to a whole other level. Dressed as they were and, probably owing to their ages and the fact that there were two of them, I actually got a shake of the head and a grunt of disapproval from Mrs. Applewhite, who lived on my floor.

Naturally, June and Lizzie found it hilarious, and they both fully burst into laughter when the elevator doors finally closed. Lizzie leaned over and kissed June through continued giggles as I pressed the button while shaking my head.

By the time we made it into my place I was finally starting to feel some of the residual shame and embarrassment abate, quickly being replaced by rising lust. In the time before June came into my life I had been having some pretty decent sex for a guy my age. I did well with hook ups, owing to my proximity to Broadway and the fact that I had stayed in good shape and had all my hair. Plus, I had one fairly regular play partner who just happened to be married to a former coworker of mine.

For the previous few years I sometimes had to rely on help from the pharmaceutical world to get and keep a really good hard on, but I honestly hadn't needed them over the last few months. Since things started with June, and now with both her and Lizzie, I was usually so turned on that getting hard happened involuntarily, like when I was young.

So when I broke away from them and fell sideways onto the couch, I could already feel a stirring from between my legs. They resumed kissing and were now also groping at one another, so I began to rub the palm of my hand along my hardening cock as it protruded down into the leg of my jeans.

We had all previously been together, so we didn't need a lot of preamble. And judging by the amount of time that June had been spending in Lizzie's dorm room over the previous week, they were now even more comfortable with one another sexually than when they first drew me into a threesome.

I took a nice long hit of weed and untied my shoes, kicking them to the side. As the girls stumbled onto the loveseat, intertwined in each other's limbs, I took the opportunity to pull my jeans off and resume rubbing my now fully hard dick through my boxers.

June looked over at me and she had fire in her eyes, showing once again how much she liked to be observed. She made a big show of putting her hair back in a ponytail and then yanked Lizzies jeans off leaving her there in just her lace trimmed black body suit.

Lizzie moaned and closed her eyes as June unsnapped the body suit, exposing her bald pussy. June turned her head to watch me watching her as she explored her friend's crotch, licking, kissing and smelling her way around. When June fully dove in and began to swirl her tongue around Lizzie's wet lips I rid myself of the rest of my clothing and began to stroke in earnest, but it was short lived.

"Ugh... that feels so fucking good June, but... you're the birthday girl. We should be taking care of you!" Lizzie said, pushing June's head back and glancing over at me.

I jumped up off the couch and grabbed my balled up flannel shirt to use as a knee rest, folding it and dropping it on the floor in front of of June. Lizzie pulled her body suit over her head and pushed June back till she was laying against the arm of the loveseat. All that she needed to do was spread her legs wide for her impossibly tiny skirt to push up and out of the way.

"These are new." I absentmindedly observed as I ran my fingers over her gorgeous white panties.

"A birthday gift from LL..." June said while running her hand over Lizzie's cheek.

Lizzie leaned forward and started to kiss June while bridged over me, making a perfect entry point for me to nuzzle my head up June's leg in the direction of these new birthday panties. As I kissed my way along June's hard girl cock I could feel Lizzie's big tits lightly grazing my shoulder from above as they kissed.

When I moved June's pretty panties to the side and took her into my mouth she moaned and reached to grab a fistful of my hair. Any thought of having some alone time with June's raging hard on went out the window right away, as Lizzie nudged her face down next to mine.

I grudgingly moved a bit to the side to allow her better access, and after a few moments of trying to find the right angles I was happily circling my tongue around the head while Lizzie's ran up and down the shaft. All as June was playing puppet master, with a hand on each of our heads.

Eventually Lizzie took full possession of June's girl cock and she was once again showing off her admittedly masterful cock sucking skills. So I stood up and yanked June's top off so I could spend some time with her equally hard nipples. I perched myself on the edge of the loveseat and bent down to take the left in my mouth while I grazed my thumb over the right.

"Fuck you guys... you've got me so fucking horny!!! But... oh god babe... that's... fuck, that's good. But, I'm the birthday girl so I get what I want right?"

We both made noises to answer in the affirmative while our mouths were busy, and the vibrations appeared to cause June to lose her train of thought for a second. Her head flopped back on the arm of the loveseat and her hand reached out to grasp my dick.

"Oh fuck, this feels so fucking good, but... stop. Please?"

I grudgingly released her nipple and stood up, breaking her grasp on my cock, but Lizzie was undeterred. June and I both watched as she snaked her tongue out and ran it along June's balls while she had her mouth full of girl cock.

"Come here and kiss me babe!" June ordered, and with that Lizzie finally withdrew leaving a sloppy mess behind.

After they broke their kiss, June said that what she wanted for her birthday was for her and I to DP Lizzie. Naturally, I was fully on board with this gift and had been looking forward to it since the first time we were all together. During our previous romps Lizzie hadn't been prepared to try it yet, but apparently they had been training during all those nights they spent together, and she quickly agreed.

I ran into my bedroom and grabbed some lube, and when I returned June was laying a blanket over the couch. She directed me to sit, and then for Lizzie to suck me to get me ready. As soon as Lizzie crouched in front of me, June went to work with her fingers on Lizzies little asshole.

I was watching intently as Lizzie slurped away at my cock and when I looked up again, June was rimming Lizzie. Eventually, when our eyes met, she raised her head and smiled and winked at me before she went back to fingering Lizzie's ass. After about a minute of this Lizzie raised her head and turned back to look at June.

"I'm ready babe."

June giggled and made a big show of slapping Lizzie's ass as they both got up off the floor. Lizzie moved toward me and straddled me, easily sliding her well prepared pussy down around my equally ready erection. I lost track of June as I instinctively raised my head to begin delighting in Lizzie's big beautiful tits.

As I sucked and nibbled from one to the other, Lizzie was grinding into me and she felt amazing. When she suddenly went still and raised her chest I figured June was getting ready to enter her ass. Then I felt the pressure in Lizzie's wet cunt increase as June pushed her way in.

"There we go slut... you're all filled up with cock!" June said, causing Lizzie to clench her pussy tight on me.

"Holy shit! I love feeling you both moving inside me. Christ! This is amazing!"

First we both were just taking soundings, seeing how far we could push our way into her holes at the same time, but without coordinating we ended up in a very pleasing rhythm where I pumped my hips up to fill Lizzie's pussy when June pulled back out of her ass. Then I pulled back while June plunged in, all to great effect.

In the midst of all of this I was mauling Lizzie's tits as they hung there in my face. I had visions of June and I coming all over them at the same time, and just the thought made me growl with enthusiasm.

After just a few minutes of fucking her this way, Lizzie asked if we could switch it around. June pulled out of her ass and walked to the linen closet to get a towel and some wet wipes to clean her girl cock off with. While she was doing that, Lizzie took the opportunity to clean my cock up as well, savoring the way she tasted on me.

"I wanna be able to kiss you while you two fuck me!" Lizzie explained to June, as if she had to justify our position change.

"Get up Sully, I wanna lay down on the couch." June directed me, and I quickly complied.

June stretched herself fully out, with her toes pointing and her arms above her head as if to take up as much space as possible. She looked like the very personification of feminine sexuality all stretched out like that; the presence of her hard girl cock only seeming to emphasize it in some way. And I wasn't the only one who noticed, either.

"Fuck you're so hot babe!" Lizzie said as she threw her leg over her BFF and lowered down to begin fucking her.

I just stood there for a moment watching them, lightly stroking lube onto my cock. Despite the fact that we were all obviously willing participants, in that moment I felt like a menacing observer, almost as if I were spying on them from the crack in a door.

June must've felt the same energy, because as Lizzie rode her, she kept peeking over at me jerking myself, but she would look away when our eyes met. Knowing how much she liked to be watched I considered just looming above them, stroking myself as I watched them fuck. But after a few minutes of this, June seemingly had her fill of exhibitionism.

"Come over here and fuck her sexy fat ass Sully!" She demanded.

I applied some fresh lube and slowly found a spot on the couch in the tangle of lady legs. I took hold of Lizzie's hips, holding her still momentarily as I took aim and eased myself into her ass.

"Goddamn! I love feeling so fuuuuuuull!" Lizzie moaned before she and June resumed sloppily kissing.

My exhausting personality tried to butt in with conflicted feelings about how much closer they seemed to be during our three way sex, but in a sign of incremental progress I shook those intrusive thoughts away and instead focused on how good Lizzie's round ass looked as I fucked it.

This focus brough with it intensified vigor, and before I knew it I was really throttling Lizzie's hole. June began to match my more aggressive approach, and after a few moments of lining things up just right we were both pounding into her. Only this time we weren't taking turns, instead we seemed to synch our motions up, each thrusting fully in at the same time.

June had bent her legs at the knees and had her feet flat on the couch so she could buck up into Lizzie's pussy, and I now had one leg on the floor and one on the couch as I repeatedly plunged in and out of her ass. Lizzie was all but convulsing between us, with her head tucked off to the side and tight against her own shoulder, her eyes tightly shut.

It was all too much for me and let them know that I was close. June instructed me to come in Lizzie's mouth, so I pulled out and starting pumping my cock in her face, taking her chin in my hand to keep it lined up correctly. As I started to come I fought the urge to just plunge my cock in her mouth, knowing ass to mouth turned her off, and so I just kept shucking my hand over my cock as I did my best to get as much as possible in her mouth.

"Kiss me Liz!" June commanded

"Thuch a lil cum thlut!" Lizzie said through her full mouth before lowering it to June's.

They kissed and slurped on my come as they continued to fuck there on my couch. I grabbed another towel and started to clean myself up, feeling a bit left out. Its never fun to be the first penis-haver to come during a three way. Luckily their frantic fucking meant I didn't have to wait long.

They were slapping into one another as their mouths remained joined together but Lizzie pulled away and shoved her face into the crook of June's neck as she announced that she was coming yet again. June groped at Lizzie's ass as she picked up the pace of her thrusting and as Lizzie's breathing started to return to normal June's was quickening.

"I want you both to suck me till I come!" June ordered.

They both got up off the couch and Lizzie instantly took up a spot at her feet, just off to one side to leave space for me. By the time I had knelt in my designated spot Lizzie was sucking with abandon. I never got an opening to join in, because as Lizzie took June's full length in her mouth she began to make sloppy noises with her throat and whatever she was doing fully pushed June over the edge.

Lizzie never let up, and as June began to come in her mouth her knees eventually buckled causing her to put her hand on my head for balance. June finally fell back onto the couch and Lizzie moved her head to rest on June's knee.

"You two really know how to treat a girl on her birthday!" June said as she ran her fingers through Lizzie's hair and looked over at me.

With the boundless energy of girls in their early 20's, they both shortly sprung up and raced to take a shower together in the master bath. I gave myself a bit of whore's bath in the kitchen sink and pulled on a sweatshirt and shorts before ultimately making myself a PB&J.

---

By the time our festivities wrapped and the girls had taken a long shower together it was nearly 1 AM. They retreated together into my spare bedroom to go to bed, each kissing me on the mouth as they went.

I got my own shower and climbed alone into my bed, taking with me the ever louder intrusive thoughts that said I was being shouldered out of June's life.

I get so fucking sick of myself sometimes. Even when I know I'm being ridiculous I can't seem to stem the emotions that crop up in the wake of these anxieties.

The clock shown 2:18, and I was sill there wrestling with conflicting thoughts and emotions. I was serious when I told June I didn't want to be in a relationship with her, but I also loved having her in my life in this new and very personal way. I had pushed her to try things with other people, so I very well couldn't feel slighted that she seemed to have an even stronger connection with Lizzie than she had with me.

They had known each other their entire lives and had always been very close. So it only stood to reason that their lifelong bond would show up quite strongly in their fucking. The logic seemed rock solid to me, and soon I felt the anxiety start to wane as exhaustion seemed to sweep over me.

Then, my door opened.

"You're not in here worrying and overthinking are you?" June said softly as she pulled my covers back and joined me beneath them.

Do you know what it feels like to be fully clocked by a newly minted 22 year old? Its quite destabilizing, but also remarkably comforting all at the same time.

"Uh.. guilty."

"Shit Craig... you really need to learn how to turn your brain off sometimes, ya know?"

"I do know. My therapist knows. My ex's know, and you seemingly know better than the rest of them!"

"I had so much fun with you both tonight! You are both so special to me, but in different and very important ways. I... I don't want to make things worse here, but I think its important that I explain this to you. Here goes: I feel like I can be myself around her in a way that I can't with anyone else. She was the first person I talked to about feeling like I was trans, and that was when we were like 14!"

"I get that Junie, and it's not a problem. I..."

"No, let me finish! Before I even started to transition she would let me try on her clothes up in her room when we had gatherings, and when I was wrestling with what to do she would just say stuff about my 'gorgeous little figure' and my 'pretty face' almost like she was sure that I was a girl even before I was.

"So she is like... uniquely special to me if that makes sense to you. But so are you Sully! And even though its in a different way, its no less special to me. When dad brought me downtown to have lunch with you that day I was excited, because I knew I'd feel comfortable with you, and that you wouldn't judge me. But, what I wasn't prepared for was that you would be in to me, and... I'm not gonna lie... It kind of messed with me.

"Having you, this like... regular dude be into me and want me makes me... I don't know... it makes me feel like a real girl, ya know? There are plenty of seemingly straight guys out there who watch tranny porn and might even fantasize about being with a tranny, but I feel like you're not some gross chaser. You're just a guy who likes me because I'm a girl."

"Yes. I am, and I do."

"And you were my first.... and you made it so fucking special, like way more than I could have ever wished for. Plus... you've been so good to me. I'm sorry if I haven't said 'thank you' enough for all the help you've given me, and all the money you've spent on me... and for giving me a place to live, but please know that you are just so fucking special to me and, even though I don't think I'min love with you anymore, I definitely love you and I hope I can be in your life forever."

With that she laid her head on my chest and as I stroked her hair I felt a tear drip down from her eye. I craned my neck forward and kissed the back of her head before lightly turning her to face me.

"I love you too Junie. And I'm more than happy to do whatever I can to help you. I hope you know that you will always have a place in my life, and you can always come to me."

She stretched out to kiss me and then just laid there for a second, our faces right next to each other. She kissed me again, and then pushed up off the mattress so that she was on her hands and knees, but with her face still right by my head.

"I worry that the things that make you so special to me are the things that make you pull yourself apart. I just wish you'd be nicer to yourself Craig."

"Me too sweet girl, me too."

I thought she was going to jump up and return to sleep with Lizzie, but at that moment she pulled the covers back and began kissing her way down my torso.

"I have a way to shut your brain off" she said as she plunged her hand under the waistband of my boxers.

After I came in her mouth she kissed me again and got up and left the room. I glanced at the clock again and it read 3:03. That was the last thing I registered before I slipped off to a very restful sleep.

----

Chapter 7 arrives in July.