Ryan & Tracy's Chicago Weekend

It had taken too long, basically all day, to get to Chicago, and the last two hours were brutal, covering 12 miles or so. Seriously.

But to the hotel, and into our suite. An added bonus was having a deep, Japan-style spa tub, and it didn't take long for Tracy to plunge right in. She invited me to join her, but it wasn't really conducive to seduction: a two person rectangle, with seats, so you'd sit facing one another neck-high. Therapeutic, but not too sensual. Instead, I stripped for her and showered behind the glass next to her, soaping and stroking my cock as she watched.

After dressing, Tracy looked gorgeous. She'd done hair and makeup just so she'd look great in photos, which I'd promised. She'd brought along her cute red baby doll and red thong to sleep in, and looked stunning in it! So tall in her heels, I positioned her by the window drapes for some first photos, and my baby does enjoy posing. Then, I asked her to open the drapes.

I'd been savoring this moment: sharing her sexiness is a particular thrill for me, like that time in Vegas. We were on the eighth floor, in a corner room having floor to ceiling glass and long drapes. Opened, she'd be in full view of the office building across the street, perhaps from the street below. She mentioned that; I said, "That was the idea". She didn't hesitate, and with a cute smile, drew the curtains aside and resumed her posing. I took a few more shots, then had her give me her back side (and to let "whoever" see her other side as well).

I don't get her in tall heels very often, so I wanted to keep us standing while we kissed and caressed. And, holding her like this, got me to thinking: she's just a bit shorter than me with 4" heels...I wonder if she could "do me" standing up, this way? We posed back to front, and I reached behind me to stroke between her legs. Almost perfect...just about the right height to penetrate me.

We got to bed finally, and all the hot soaking had put my baby into a state. That red thong she was wearing was the same one I'd peeled from her the first time we were together, and that was a nice memory. And delightful of her to bring that particular garment along on this trip.

I had her pose a bit for me on the bed, first putting her red babydoll just a little too high on her thigh as she lay on her side, like those hottie pictures that "almost" show what you want. Then, I put her on her tummy to give me what I wanted, some clear shots of her sexy ass in that red thong. Peeling it from her, and diving between her legs, it was great to finally taste her.

She came so quickly, and so forcefully. Her legs were so soft, her thighs so strong, it was fun to pin her hips to the bed while I sucked her clit into a second and third orgasm. Fantastic. I love hearing her cum. She asked me to blow on her clit, and just shivered in response, and asked I her if she could give me another one. I tongued her again, this one came even harder, it's still so warming to think about.

And then, my baby asked me what I wanted. That was an easy one: to be stripped, and have her strap on and fuck me.

I'd still been wearing board shorts through all this; Tracy said, "You're still dressed?" I said, "I figured when you wanted me naked, you'd do something about it". With that sexy, sly smile, she went to work on me, sliding my shorts off over my rigid cock to have her boy all naked and ready. She stepped into the harness, not bothered much by her heels, and I put a rolled pillow under my back to be ready.

Lately, I've just wanted her to take me...just lotion a cock and make me take it. I like that feeling of being "taken" and made to be hers, quickly and suddenly. I helped her position, and felt her strength as she forced in the head. That's an incredible moment when the head finally breeches, and I feel the length of her shaft enter and fill me. She gave me long, smooth, stroking, some deep kisses, and I could caress her hair as I felt the flood of belonging to her again.

As often as we've done this, I'm still amazed at the progression of emotions that seem to flow each time. That initial craving to have her, the heat in seeing her wear her cock, the nervous excitement as I lay ready and she lotions. Then: pressure as her cockhead begins to make me yield, and a rush of feeling her enter me fully immediately brings...some sort of quiet warmth, actually. A sense of belonging, and of loving her so much; of being this vulnerable to her, allowing her to be inside me.

I savored that for a while...and then...it's about: OMG how fucking hot is this? My sexy, so-curvy baby is plunging a hard cock deep into my ass. It's SO pleasurable to feel it inside me, especially missionary style, her cock massages parts inside that love it, and the visuals of it are spectacular. This emotion is: well, just lust, about letting this just flow, having such a dirty boy and girl get together and give each other what they crave. Lying back, arms above my head, knees to my chest, totally penetrated and vulnerable. Or wrapping my arms around Tracy, locking my ankles around her hips, pinning us together, so loving.

This night, I wanted to feel her fuck me standing...and from the measuring before, it seemed plausible. So I pulled away from her, and got us standing. She looked great, in that leather thong, wielding a glistening cock that seconds before had been deep inside me, all tall in heels and red lingerie. I got next to a wall, grabbed her cock, and placed it on my opening. One slight push, and Tracy was buried inside me again. It took just a little bend of my knees to make a perfect fit, which looked even hotter with my leg muscles all tensed and flexed as I was being pleasured. Tracy could watch in a full-length mirror not far away. I knew this scene was completely pornographic and it felt great. Both of us fantasized about having Nicky here to see us; both to see Tracy take me this way, and to let Nicky get some video of Tracy doing me. Glorious! Balconies, elevators...lots of fantasy possibilities in the future!

I had to cum, so I wanted to fuck Tracy's ass to do so. I helped her remove her cock, and also her red lingerie...now just all Tracy, high heels, and nakedness. I put her on the bed over a pillow, lotioned her ass and my cock, and slowly penetrating, felt her warmth and tightness. My mind and actions weren't too connected...something about the heat in the room and being too fast...so I slowed down, and just savored the shape of Tracy's booty, how good it felt to have my cock sliding in and out. And that's all it took to have me explode with shot after shot of hot cum into her ass and onto her back. Completely spent.