It was very early in June. The summer I graduated from high-school. We had just learned that my dad had been offered a big promotion to Regional Sales Manager and we would soon be moving to Indianapolis. Also during our Senior year, Stephanie and I had grown apart.
We still loved each other but we weren’t the same people we were at 12 or 13. I had several colleges interested in me for football, one of them was Michigan State. I had planned on going there in the fall and was looking forward to playing as a Freshman. Starting over in Indiana, with my choices being Indiana University, Purdue, or Notre Dame, none of whom expressed interest in me, was not as promising. Especially as a “walk on.”
To spend some time together as a “family” my dad booked an entire week in a luxurious and expensive hi-rise one of his friends owned on the Gulf coast of Florida (Tampa/Clearwater Beach area). I hadn’t been since we had gone a few years ago and took Stephanie along so while I was looking forward to it, I was also kind of bummed out because I’d be “by myself.” It just made me miss her that much more.
The first couple of days it rained. I hung around my room playing on the Internet and also made use of the gym. The next day it was sunny and very warm in the 90’s (F). I decided to go for a walk just to get out of my room and, who knows, maybe meet someone.
Before heading to the beach, I stopped by a local convenience store to grab a Red Bull and some tanning oil. I was wearing a “Michigan State Football” jersey. I didn’t notice him at first. “Spartans huh? So are you guys gonna win the Big 10 this year?” I turned around. He was maybe 6’ tall, long “dirty” blonde shoulder length hair, blue eyes, cute freckled nose, slim body, great legs (Fuck, you’ve read my other stories, they
always are…
).
I laughed and said “Well maybe… are you from Michigan?”
“Yeah, but I got the hell out of there years ago. Couldn’t take my parents giving me shit anymore. So I moved down here.”
“Where do you go to school?”
“A community college in Tampa. Studying to be a legal assistant. But I really want to get into movies.”
He was probably right about that. Verrrry good looking. Handsome yes, but really, I would have to describe him as “pretty.” Tall and with an athletic body. I couldn’t help notice he had no body hair. Also he was nicely tanned with long legs. I was getting kind of a funny feeling (a good one) talking to him and my cock began to respond.
“My name’s Andy.”
“Anthony. What are you doing down here anyway?"
“My dad’s getting transferred and he thought it would be good for us to spend time as a family. We just got here Saturday. Why did you think I played for “State”?
“Jesus. Those shoulders and arms. Plus you must be at least 6’4” or 5”. You know, it’s a lot more fun if you’ve got someone to show you around.”
“OK.”
“Have you ever been to Florida before?”
“Yeah, but it was a long time ago.”
“Well there’s a lot that’s changed. By the way Andy, I can tell you are upset over something. Maybe later you can tell me about it.”
Anthony and I head towards a club catering to young people. It’s an “under 21” place so no alcohol but it looks like fun. Kind of like a rave. I notice there are many gay and lesbian couples. There is a booth in back where it’s a little quieter so we can talk. We order drinks. He tells me how his parents basically threw him out one night after an argument. He hitchhiked down here and found a part-time job, sleeping on the beach until he found an apartment. I discover that Anthony is 21, three years older than me.
I tell him a little about Stephanie, how we were friends in school, and that she was my first love. I explain that the move caused problems in our relationship and we had basically “split-up.”
“That’s too bad. She was trans wasn’t she?”
“How did you know?
“I can tell. Just from the way you talked. And the way you acted when we met earlier. Hope you’re not mad Andy. I just have a lot of experience” Anthony says smiling.
“Her name had been Stephen. I really loved her.”
“That’s so sweet” he says.
We leave the club and go for a walk. Anthony shows me around and tells me things about the area I never knew. It’s nice. I don’t know if this is leading somewhere or not but I’m enjoying our time together. I know one thing, it sure beats hanging out in the fucking hotel.
Hours have gone by and it’s starting to get dark. Anthony asks me if I’ve ever seen the sunset on the Gulf of Mexico before.
“Yeah. But I'd love to watch it again with you.”
Giggling, he says “Are you asking me on a date Andy?”
“Ummmm…. Yeah sort of….”
“I know a great place to watch it from. Let me go in here first and get something to drink.”
He goes into a drug store and comes back with a bottle of Tequila.
“Figured you would like this Andy, if not that’s OK.”
I follow him along the shore to an out of the way place far away from the public areas and we sit down propping ourselves up against a dune.
“It’s beautiful isn’t it? This is where I used to sleep before I found a place. I always loved watching the sunset.” He takes a swig and passes the bottle to me. I take a drink and hand it back.
Neither one of us says anything. It’s a truly beautiful night. I noticed that we are sitting very close, our legs touching each other’s. He has slipped his hand into mine. We look at each other. His eyes are so beautiful in the fading sunlight. There is a brief pause “Anthony…” I say. Then before either one of us knows what’s happening we are kissing. First gently then more aggressively. Open mouthed and with the tongue.
We stop for a second. As if to check with the other if it’s OK. Words aren’t necessary.
I reach in his shorts and pull Anthony’s cock out. He does the same with me. We are both about the same size and also circumcised. We are already dripping pre-cum. He begins to rub our cocks together as I pull his shirt up and lick his nipples, occasionally biting them gently. His body is gorgeous. I push him gently back onto the sand and suck and tease his hard cock. He sighs and moans, as I bring him closer to orgasm.
Trading places, he works my cock over until I don’t think I can stand it. He has a firm grip around the base and he uses long slow strokes. Taking me deeply into his mouth. I’m amazed that he doesn’t gag. I’ve never had my cock sucked like that before. In fact this is my first sexual experience with someone besides Stephanie. Anthony is wicked. God it feels so good! I must seem like an amateur to him but he doesn’t say anything.
Without thinking I say “Fucking god, baby. I’ve never had anyone do it like that before.” Anthony just giggles.
Having driven each other to the edge we get back up and kneeling in the sand we continue to rub our cocks together until we both shoot our loads all over each other. The sun has set and been replaced by moonlight. The sand is still warm. Anthony snuggles up to me the same way Stephanie used to. I can tell how relaxed he is. He puts his arm across me and rests his head on my shoulder his long blonde hair falling softly on my chest. I kiss him gently on top of his head as I hold him close.
We fall asleep. When we wake up it’s still dark. We must have just dozed off. I ask Anthony if he would like to go back to my hotel. He says “Sure.” We get dressed and “sneak” back in to the hotel. My parents had been trying to call me on my cell phone. I call them back and let them know I went to a club and ran into a bunch of kids from Michigan and just lost track of time.
Anthony and I take a shower together than climb into bed. We spend the rest of the night talking about well, everything. I tell him about growing up in Michigan and how I played football. Also about how Stephanie and I met and the night she told me that she knew she was a girl from about age 4 or 5. He also tells me a lot about himself.
“It was basically the same with me. My parents didn’t understand at all though. My dad said he didn’t want a ‘sissy’ around and told me to get the fuck out. I thought coming down here might help and maybe I could get into movies. You know.”
“Are you sure that’s what you want?”
“Yeah. I love sex and I would never do anything dangerous… unless you wanted to Andy. But I thought I could do that while I transitioned then maybe I could afford to have surgery. I’d love to have bigger boobs someday. Maybe even SRS. You know what name I’d like?”
“What?”
“Anna. I’ve always liked the sound of it. What do you think Andy? Maybe one day you’ll see me starring in something. If you do I hope you will remember this night.”
“Anna. That’s a beautiful name. I think
you’re beautiful. You know, why don’t we just enjoy the time we have? You don’t have to decide anything right away.”
The rest of that week was awesome. Anna and I spent every day together. And we made love every chance we got. Later that week I introduced her to my parents. But there was something in her past that had happened to her that she wouldn’t talk about. I could tell. I knew someone had hurt her. Not physically but emotionally. I also understood she had to work it out on her own. Unlike Stephanie, it was obvious that Anna never had the support of her family nor did they have the wealth that Stephanie’s family did. So when we said goodbye at the airport I realized I probably would never see her again. We kissed for the longest time. People were staring at us. But so what? The last thing I remember was looking into her beautiful eyes as I gently touched her face. She took my hand and kissed it. Then turned and walked away.
A few years later I bought a new DVD for my “collection.” The star of the movie was Anna. She was even more beautiful than what I remembered. Married to my first wife by then, I thought back to that summer night we watched the sunset. Just like she would have wanted me to.
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