These are based on true experiences. Sometimes, even I had trouble believing that they actually occurred as they seemed like porn movies. As always, I love feedback and a 'Thank you' goes out to those that have emailed me. I hope you continue to enjoy my enjoyment.
A very special and huge 'thank you' to Goamz86 for editing.
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"You think you've pushed my boundaries?" I asked mischievously as I fell off of Sam and crashed back down onto the bed.
Sam laughed, "I'm pretty sure you have a few boundaries but who knows how far down the road they are...I'll get you there." He rolled out of bed and went to the bathroom.
"I'd like to see that." I said, starting to feel sleepy again as I lay there in the warm sun, curled up with a warmth shining on me and sitting deep in my ass.
"Don't worry," Sam laughed, "I have big plans for you. Big plans..."
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Over the next several months, Sam and I escalated our torrid affair. One thing that Sam did to make sure we didn't get too attached (especially me), was to encourage me to have sex with other people. Sam especially encouraged me to enjoy my new found sexuality. I was still very nervous about hooking up with any new guys though, and I was getting more than enough from Sam.
I continued hanging out with my straight friends and even though I was getting my ass drilled by Sam's cock on a very regular basis, by all appearances, I was still the same "Matt" to my social circle. Some of my straight buddies even knew that I had a buddy that I partied with in the building and a few had even met Sam, but no one had any idea that he was my "boyfriend". Sam often loved fucking my ass before and after I had been out with them.
"What would your friends say if they knew you loved cock? What would they say if they knew what a fag I've turned you into?" he'd ask as he pounded my hole.
"I don't care! I'm a fag...it's who I am...I need it, daddy!" I'd respond.
A few days before my birthday, I came home to find Sam had bought me a present. I quickly opened it up.
"It's part one of your present," Sam said, "Part two is in the card. Part three is...you'll see."
I pulled three jockstraps out of the bag, all brightly colored - although one was basically see through, and all perfectly designed to show off my ass for a man's pleasure.
"Wow! I feel like a lucky girl!" I laughed.
"Wait till you read the card," Sam smiled.
I opened the card up and read it. "One hour of massage. DT Massage Center." Underneath where the address was written, Sam had added, "Jockstrap not required! Happy Birthday you sexy stud! XXX"
"PS You'll need to take next weekend off starting Thursday night. Jockstrap definitely required."
"What do you have planned?" I asked grinning at Sam.
"Pack your bags - we are going to Vegas!"
I was shocked that Sam had booked a trip for us together but at the same time, very excited.
"I really hope you can take the time off next week?!" Sam nervously laughed.
"I will make time. I have a feeling this trip is going to be unlike any trip I've ever taken to Vegas."
"I guarantee it," Sam said as he cocked his head. "I've also invited Alex and a friend of his. It is going to be a total 'boys' weekend'." I was pretty sure what an "all boys" weekend meant - sex, lots of it and from the sounds of it, with multiple partners. I was so in the moment of thinking about Vegas, I almost forgot about the massage and what that might entail. Instead, I grabbed Sam's cock through his pants and smiled, "I guess I should say thank you properly?"
"You know what to do cocksucker," Sam said deadpan.
I dropped to my knees and pulled his cock out of his pants, not even pulling his pants and undies all the way off. I opened my mouth and took his semi-hard cock to the root, pressing my nose against his trimmed pubes. Instantly I felt his cock grow. I pulled off enough to catch my breath before deep throating him repeatedly.
Sam's hands cradled my head and he moaned my name, "Mmmmatt. You are such an incredible cocksucker. You love being a cocksucker, don't you?"
I moaned approvingly around his cock before I let it escape my mouth and looked up at him from my knees, "I love being a cocksucker." I licked his cock and again deep throated him. After a few minutes of this, I could feel Sam's cock get harder and I knew he was close.
"You want my load, babe?" Sam groaned.
"HmmmmMmmmm!" I moaned around his cock. I felt his cock get even harder and start to spurt into my mouth. I swallowed as fast as he shot, enjoying each drop.
"Yesssss! Drink it up, babe!"
I pulled back a bit and jacked his shaft to make sure I squeezed every drop before I released him from my mouth. I clenched his cock in my hand and saw a final drop of his cum appear and immediately licked it off, looking up at him and smiling.
"Thank you for the presents!" I smiled. At times like this, I almost felt like a girl.
"You're welcome, slut. Anytime."
I stood up and adjusted myself, as giving a bj almost did as much for me now as it did for the cock I was working, looked at Sam and smirked, "That never gets old."
We opened some beers and chatted, discussing where we would be staying in Vegas and who Alex was bringing.
"His name is Cory. I've met him a few times and he seems like a nice guy; Good looking, Tall enough, Easy going. We should all 'click' if you know what I mean. Alex knows what we are looking for. And if it doesn't happen, we will still have a lot of fun, I'm sure."
"This should be a very interesting trip to Vegas...much more interesting than the last one I took with my ex-girlfriend..."
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Vegas weighed heavily on my mind with how open the trip was going to be. I was still nervous about being seen and I was far from opening up this part of my life to the public. I knew in reality though, that I was very unlikely to see anyone in Vegas that I knew. The easy part was that Sam, Alex and myself didn't "appear" gay. I didn't know about Cory, but Sam said he was a "guy's guy" so that also eased my fears.
To help me relax, Sam booked my massage a few nights before we left for Vegas.
"You're going to love it. Ted is a professional."
"A professional?" I asked, "What kind of professional are we talking about?"
Sam refused to give me too many details and looked at me with a smile, "The kind of professional that will help you relax and work out those tight spots. You're going to love it...trust me...have as much fun as you want and are comfortable with."
The next night I went to the address Sam provided for me. It was in an upscale apartment building downtown. I buzzed myself in and went up to his place. Ted opened the door and I found myself staring at a near perfect specimen of a man; tall, dark, rugged looking, deep voice, chiseled build. Ted was not all what I was expecting, although to be honest, I wasn't sure what I was expecting.
He introduced himself and said he worked from his place and we went over what I was looking for - a relaxation massage.