A Bloom in June Ch. 03

****This is Chapter 3 of an ongoing series about a middle aged guy having a fling with the 21 year old trans daughter of a college buddy. I think it can be read as a standalone but I don't go out of the way to add call backs or context, assuming that most people will read the first two prior to this one****

"Listen... " June said while laying naked on top of me "I don't want you to crash out, thinking I'm catching feelings or anything, but seriously... how are you still single Sully?"

"Trust me... its not a mystery or anything..." I said into the crook of her neck, causing her to wiggle around on top of me as my breath tickled her.

"No seriously! You've got a good job, even if I don't understand anything about it and almost fall asleep when you try and explain it to me. You've got a cool pad and car, most of your hair, a pretty amazing beard that is giving total daddy energy. Not to mention that just about everything you believe in is enough to make my bible thumping parents snap."

With that she rolled off of me and then kept rolling until she landed one leg on the floor and sprung up to stand looking back at me. It was Friday night and we had just had sex for the second time ever. After I got back to the hotel from an unexpectedly long work day I found her waiting naked in bed.

I had hoped to take June to see a show, but unfortunately I didn't even leave the office till 7. So she had to make due with me sucking her cock a bit and then rimming her until I was good and hard. I bent her over and fucked her as hard as I could until she whimpered and told me she was going to come. After she was done twitching I pushed her to the side a bit so I could admire the wet spot she had left on the sheets before picking up the pace again. I grabbed her hair in my fist as I finished, pumping my load inside her.

From there I had laid down and June joined me, laying on top of me. As we cuddled I felt my come drip down her inner thighs on to my pelvis. She felt so good in my arms and if I'm being honest, I had a quick thought about what being in a relationship with June would be like: all the goods and oh so many bads. So after she had dismounted me and stood over me I tried to be as honest with her as I could, but I also remembered how emotions can get magnified for the person you lose your virginity to.

"June, I'm kind of a handful. I can be a good time, and a great partner for a few years. But, I'm also very particular about certain types of things that don't seem like a big deal at first, but apparently end up chafing over time. Judging by my two relationships as an adult, I'd say right around seven years, or, more accurately: right around 5 years of living together."

"I was only like 17 when you and Miss Rene broke up, but I remember thinking that she was crazy. Of course, my dad thought she was a lesbian because she was kind of thick and played softball at Ole Miss, so that's what he and Mom said caused it."

As I got up to join June in the bathroom for a quick post-sex/pre-dinner clean up, I told her the story. Rene was a few years younger than me and we hit it off right away. After a few years dating we got serious and bought a place together. This is oversimplifying it a bit, but after a while, the things she liked about me began to become common place and expected which meant that they weren't special any longer. While the things she didn't like began to get magnified. But what really did it was her insistence that the changes I made to accommodate living with her - willing made, I should add - were examples of her improving me.

"We would be having dinner with people and she would go on and on about how she had 'trained me' as if I had been some super rough around the edges frat boy who she convinced to wash his sheets and towels more than once a year. Toward the end I remember making the point to her that there were things I didn't have a strong opinion on which I would modify my approach to for the sake of harmonious living, but that if we weren't living together I would go back to doing the way I liked."

"Seems logical to me." June said, pretty convincingly as we both got dressed.

"I guess not. Rene accused me of being fake because I changed how I did certain things to please her. Like, she wanted me to fight to keep using dryer sheets instead of liquid, or to insist that we not used fitted sheets because I had never had them before. It seemed astonishingly dumb to me, but somehow things like that became a really big deal over the years, although the little things often are stand in's for the bigger things no one wants to talk about."

"Seriously? That was it? My mom said she had an affair with a woman and you kicked her out."

"Oh god no. That is funny, though. I didn't know that's the story the group was telling. No, she did end up with another woman though. In fact... do you remember Elyse or were you too young?"

"No, who is she?"

"She was my previous serious relationship. We were together from our late 20's into our mid 30's. After we broke up for similarly superficial reasons she got married to Tom Cathers who we had all known in college, and they had two kids. By the time Rene and I broke up they apparently touched base to compare notes and it was THEM who had the affair. But we were already over by then."

"And they ended up together????" June said incredulously as we emerged from the lobby onto 50th Street.

"Yup. They're raising the kids together out in Forrest View Park."

"Wow. That's fucked."

"Yeah, my thoughts exactly. Lets pick up the pace. I'm starving."

I gave her more of my tragic relationship history over dinner, while trying to be as honest as possible. Lord knows I wasn't blameless in either of my grown up relationship failures. June seemed overly focused on Rene and Elyse's issues while being dismissive of the faults I was admitting to. It felt a bit nice to have her be so supportive, but it also smacked of the kind of puppy love that many people experience early in a relationship.

And that made me both extremely nervous and, naturally a bit excited too.

That night, after dinner, we returned to the room and took a shower together despite the fact that it was cramped in there. But when we climbed into bed we just made out a bit before talking some more. June was bummed out that we had to leave the next day, and frankly I wasn't all that jazzed about going back to the real world either.

So once again I did something rash and called the Airline to see about getting our tickets changed. The change fee was a killer, but some more time with June in NYC seemed worth it, and the look on her face when I said we were staying until Sunday night was totally worth it.

After a call to the front desk we were booked into a new room through till Monday morning, despite the fact that we were going to be flying back late Sunday night. That way we had a nice warm bed to spend time in rather than having to kill time in the city from check out till the time we had to be at the airport.

When I was done with all the logistic work, I turned to see June laying on her side with her head propped up on her hand, and she was just smirking at me. I leaned over to kiss her and she decided to thank me by pushing me on my back and going down on me. Her mouth felt divine and before long I told her I was going to come. She responded by furiously stroking me with just the head in her mouth until I came so hard I felt like I must've filled her up. She crawled up my body and played with my come on her tongue until I grabbed her by the back of the neck and kissed her while we both played with my load.

---

In the morning we gathered our stuff up and moved to our new room, thanks to a fantastic front desk person who got it ready early for us. After dropping our bags we headed out to grab some brunch, and as we ate I asked June what she wanted to do with our day.

The only thing she cared about was seeing a Broadway show, and she shocked me by not being interested at all when I suggested Hamilton or one of the big name ones. Rather, she wanted to see The Outsiders, based on S.E. Hinton's novel, which I had no idea was even turned into a musical. I was also surprised that she was into the 80's movie adaptation, which had a big impact on me when I watched it with my sister as a kid.

After we ate, we made our way to Bryant Park so I could take her ice skating, and while we waited for our turn on the ice I booked us two tickets for The Outsiders that night. Surprisingly for a Tennessee girl, June was a natural on the ice and she literally skated circles around me. The huge smile on her face was infectious, and even though I was less than graceful on skates I couldn't help but smile seeing her.

From there it was an action packed day as I tried to give her the complete Big Apple experience. First, we walked over to Hudson Yards to visit the Vessel where - just like every other Instagram loving 20-something girl - June must've taken thousands of pictures. The snaps continued as we walked down the High Line to Chelsea Market and then to Little Island. Frankly, I was amazed she had that much space on her phone.

While we walked around Little Island, June asked me if she had to get dressed up for the show that night. I told her that the days of people showing up to the theater in their finery were well and truly over, but then she asked if wecould get fancy. I asked her if she brought anything suitable with her, to which she replied "no, but we are in the fashion capital of the world..."

So I texted one of my counterparts in the New York office to ask her where a good place to shop would be, and within minutes we were heading toward Bleecker Street to visit Anine Bing. The staff were only too happy to show June all manner of outfits, each cooler than the last and with pretty girl names. In the end she settled on the Jo Maxi dress. It seemed awfully bland to me, so I asked her if it was what she really wanted to get.

After some pestering, she admitted that it was just the cheapest option, at around $200, and that she had tried to stay away from other, more expensive things. Without letting the sales girl hear, I assured her that as a mid-level executive with no wife or kids, I could afford whatever she wanted to buy, and she wrapped her arms around me and kissed me before running back to the change rooms to try on some other things.

After about half an hour she emerged in a tight sleeveless white tank top (which I later learned was a bodysuit) a short black leather skirt, and pointy little boots. I actually thought she had chosen to go even cheaper since, despite looking fantastic on her, it definitely seemed like something she could have gotten at the mall back home.

By the time her Ginny, Hilda, and Steel were rung up to the tune of $1,323.70 it was apparent to me that I really knew nothing about fashion. I could see how happy her little shopping spree had made her, so I was almost afraid to take her down the street to the next place I had planned to show her.

As we waked down Christopher Street I felt like a real tool asking her what she knew about Stonewall, but I thought that it would also be rude to just assume a that 21 year old trans girl knew all about it just because she is trans.

She knew as much if not more than I did about what happened at the Stonewall Inn in June and July of '69. As she stood peering at the white marble statues of the Gay Liberation Monument I was so moved by her solemnity and reverence. I was holding her bags from Anine Bing, but as she stood there looking at the monument, with a Pride flag waving in the background I was struck by the whole tableau.

So I put the bags down, pulled out my phone and took a few snaps of her among the other visitors as they all stood in contemplative silence. When she was done, she took a selfie with the actual Stonewall across the street as her background and said she was ready to go back to the hotel to get ready for our show.

It was getting dark as we descended the stairs to grab the 1 train uptown. I thumbed through the pictures I had taken of her, and in one of them she was tucking her hair behind her left ear and the look on her face was, well... indescribable. It was pain, reverence, awareness, fear, and maybe gravity all rolled into one, but that's not doing it justice.

I turned my phone and showed it to her and she looked shocked. I felt bad and put my phone down, worried that it was an intrusion, but she wrapped her arm around me and kissed me on the cheek, before telling me it was ok.

"Thanks Craig. For everything. Honestly I feel like I was an actual child before this week. Thank you for bringing me here, and for treating me like a real girl... no, a real woman."

"Its my pleasure, really. Being around you makes me feel more... alive, I guess is the best way of saying it."

She put her head on my shoulder and we rode the rest of the way in silence, or at least what passes for silence on the New York City subway. When the announcement came for 50th street, I whispered to her that it was our stop, and we started to get up. As the train was decelerating we made our way to the doors and as they sprung open she turned to me.

"I know this is going to sound really vain, but could you send me that picture you took? I think you really captured something there."

"Its candid. That's what does it. You didn't know I was taking it, just like I didn't know you were taking the few of me that you've posted. In candid moments our true selves shine through in a way that no flattering pose or just right angle can compete with. And, of course I'll send it to you."

By the time we exited the subway it was already, dark so we hustled to the hotel to change for our dinner-and-a-show date. I donned one of my suits sans tie, and June got into her new outfit, which actually went really well with her dark grey pea coat.

We had a fast but excellent dinner at a Trattoria down the street from the theater, and then made our way to the show. June absolutely loved it, and even if I preferred the movie I really loved how happy it seemed to make her.

By the time we got back to the hotel she had thanked what seemed like hundreds of times me for giving her the day of her life. I put my hand around the back of her neck and pulled her in close to me for a kiss. Everything in me wanted to throw her to the bed and rail her into the mattress, but that didn't seem in keeping with the theme of the day.

So instead, I reached down and unzipped her skirt as we kept kissing. It dropped to the floor and she kicked it to the side with the pointy tip of her boot. I ran my hands over her ass, feeling that she had no panties on under her bodysuit. So i fished under her to pull at the clasps, freeing her girl cock which I then grabbed and massaged as we continued deeply kissing.

Without breaking our kissing, I shook out of my suit jacket and then dropped my pants so I was left standing there in just my undershirt and boxers. We finally pulled our lips apart long enough for her to pull the body suit off and then drop her little pushup bra. While she was doing that I also rid myself of my underclothes.

I laid her back on the bed and climbed on top of her to resume kissing her, getting a kick out of a little moan she let escape into my mouth as the weight of my body came to rest on her. I loved the feeling of her hands freely roaming my back as our kissing got more and more frantic.

She pouted when I broke the kiss again, but her expression quickly changes as I began to kiss my way down her neck to her chest. I lingered at her clavicle for a bit just to tease her and build up her anticipation for when I would move even lower. Her breathing slowed when I finally kissed my way down her cleavage, and her eyes shut tightly before her head rocked to the side as I circled her left nipple with my tongue.

I loved licking, sucking, and kissing her small but very perky natural tits, but I had a bigger goal in mind. So after I had both nipples rock hard and glistening with my saliva I resumed the train of kissing further down. I paused again to prod at her navel which caused her to giggle and wriggle under me.

Feeling as if I had done enough teasing, I quickly kissed down over her pubic hair, taking her into my mouth and sucking as I ran my hands down her legs to spread her open. I stopped sucking her for a moment so I could slobber onto my fingers and then resumed sucking her while starting to slowly work a finger against her asshole.

She was getting harder in my mouth as I circled her girl cock with my tongue, and her arousal had a direct impact on my own. I rolled partway on my side so I could reach my free hand down to lightly stroke my own cock.

I found myself rock hard, fully stimulated and turned on by what we were doing. I wanted to take things slow but I was also dying to feel myself inside her again. So I moved my mouth to her hole and took turns licking her and probing her with two fingers.

"Please fuck me Craig." She begged.

I pushed myself up and off the bed, reaching for the bottle of lube that she had procured the day before at a local sex shop. I filled my hand and spread it over her crack, pushing two fingers back inside her, finding her more than relaxed enough and ready. After lubing myself up I climbed between her legs and guided myself inside her.

As I reached full depth she wrapped her arms around my neck and pulled me down to start kissing again. I soon reached a steady, medium pace, by no means frantic and fast, but also consistent enough to cause sweat to begin to form on my brow.

It had been a very long time since I had done anything that could be construed as making love, but the tempo and the fact that we continued to deeply kiss throughout made it clear to me that was exactly what we were doing. I got self-conscious about this for a moment and I broke our kiss and pushed myself up so our chests parted and I was looking down at her.

"Oh Craig... you feel so fucking good. In me, on top of me... just so fucking good. Your stomach is rubbing on my clit while you fuck me and you've got it so hard."

Hearing that prompted me to raise up even further so that I could look down and see how hard she was. I wrapped my hands around each of her thighs pulling her back into me to improve my entry angle. Then I reached to begin stroking her, feeling that she already had a small bead of come dripping from her slit.

"Fuck you're so pretty Junie." I said gazing down at her face as she was staring down at the work my hand was doing on her.

"I love how you make me feel like a woman Craig. I love seeing you up on top of me and feeling you pushing inside my tight little hole while you play with my clit."

Her dirty talk seemingly had the same impact on us both eliciting a deep groan from me while she closed her eyes tight and seemed to hold her breath. I pushed my cock as far into her ass as I could and then started to pick up the pace stoking her girl cock.

"Fuck... I'm soooo close. Please make me come!"

I ran my thumb and forefinger of my free hand over my tongue to wet them, and then reached up and started to tease her puffy right nipple. Now she was lightly bucking her pelvis up and down to get more friction in her ass as I stimulated both her nipple and girl cock.

When her breath caught again, I withdrew and quickly sank back into her, and after holding myself inside her for a few moments I did it again. Each time I pumped into her I also pulsed my hand around her hard member. After the fourth or fifth time she began to groan, deep in her chest.

I took real pleasure seeing two pretty good sized strands of come fire out onto her belly, and I kept up both stroking her and pumping my cock deep inside her ass as she lay twitching under me. She reached up to grab the backs of her knees, and the new angle caused her to tighten up just enough to push me over. I pulled my cock from her and added four or five of my own strong volleys of come to the mess on her pelvis.