My First Massage

When I knocked on the apartment door, I wasn't sure what to expect. I had booked a massage with a man offering professional and discrete massage "with options" for males on Craigslist. I assumed that was hinting at a "happy ending" handjob or maybe even a bj.

I've always been straight for the most part, and was on my second marriage. My wife and I have a great sex life and I've always enjoyed the company of women, but I've also always been a little bi-curious. Up until now, other than a little solo ass-play with a couple toys, I had never acted on my curiosity but now at 38 years old I was all about living life and trying new things.

My wife was out of town with a girlfriend for a concert and I didn't expect to hear from her until they got back in a couple days. Before my appointment, I prepped by giving myself a good grooming and washing up. Inside and out... I didn't expect a whole lot, but didn't want to worry about any "surprises" if the masseuse' hands got to thorough.

When the door opened, I was greeted by a tall, average built man with a friendly face who appeared to be in his mid fifties. As he looked me over, he held out his hand. "Hi man, I'm Dan. Come on in!"

"Uh, actually that's my name too... thanks" I replied as he stepped aside to allow me in. As I passed by him in the narrow entry, I felt quite small next to his 6'2"ish frame. I'm on the shorter side, about 5'7" but fit and fairly muscular. Dan probably had 40-50lbs over me.

"Can I get you a drink?" he asked. "I've got beer, whiskey, vodka..."

I was a little nervous and welcomed a beverage to help settle my nerves, "a beer would be great!"

"I'll grab us a cold one, have a seat" he gestured to the sofa in his living room. As I sat down, he returned with a cold beer for each of us. "I like to have a drink and just relax, get to know a little about each other before we get into the massage" he explained.

"Sounds good" I replied. "I've never actually had a massage so this will be new to me"

We chatted for a bit, making small talk and learning a little about each other. Dan had been married to a woman for much of his life, but since his seperation several years ago he had been primarily with men.

"Well, hopefully you're able to relax and enjoy what I offer. I can give you a basic deep tissue type massage... or...". He cocked an eyebrow and smiled "I also offer a more erotic massage."

"I um.. well, I don't really know." I cleared my throat, "what would you suggest?"

"I'll tell you what. How about we just get you situated and see how it goes?" he offered. "If at any point you feel uncomfortable, or want me to stop what I'm doing, it's all good. No pressure!"

"Ok, that sounds good. Do you have a table or something?"

"Well sort of, it's in my bedroom. C'mon, I'll show you." He got up and led the way into a large bedroom with a King sized bed. There was a large beach towel across it, and attached to one side of the bed was a face cradle. "I've got my laptop set up so you can watch a little something while I work if you like, it seems to help guys relax a little more. Unless you'd rather something else?"

"Um yeah, that sounds good. Sure."

"Ok. While I'm getting something loaded, why don't you undress and lay with your face in the cradle. Let me know if you prefer a towel to cover up a bit."

I did feel more than a little awkward at the though of being completely naked in front of him, but tried to hide it. "No, that's fine I guess"

"Anything particular you like to watch?" he asked.

"I'm not to fussy, I'm sure whatever you've got handy is good" I replied as I stripped naked and lay down, placing my face in the cradle.

"Ok, here's a good one for you." He placed his laptop on the floor directly below my face and clicked play. Almost immediately the screen opened to a sexy woman already being undressed by 2 muscular men.

"Oops! Shit, that's not what I meant to open... I can find you something else if you like" he said quickly and bent down to stop it.

"That's fine" I chuckled. I've got nothing against a little porn"

"Ok, if you're sure" he said apologetically. "Let's get started. And remember, if you want me to stop anything I'm doing, let me know. If you don't say anything, I assume it's ok. Ok?"

"Ok" I mumbled into the cradle as the girl in the porn was now being kissed by one man while the other was kneeling behind her, removing her panties.

Dan turned on some quiet background music and dimmed the lights a little, before coming over and standing directly in front of me.

"You keep yourself in great shape. This is a bit of a treat, a lot of the guys that come for a massage don't" he chuckled lightly.

I felt myself flush with the realization that as he spoke, he was looking at my nude body laid out in front of him. I then heard him open a bottle of oil before feeling a warm trickle over my shoulder blades.

"Is the oil warm enough?" he asked as he placed both hands on my upper back, beginning to spread the oil. I answered with a nod as the warmth of the oil and the pressure of his hands on my back and shoulders almost instantly seemed to relax my entire body.

On the laptop, the girl was now expertly licking and sucking one mans cock while the other man had his face buried in her pretty pussy. I could feel the stirring in my groin as I watched the scene.

Dan continued to rub my upper back and worked my shoulders and arms with expertise. I could see getting use to this! After spending a generous amount of time here, he walked around to the other side of the bed and began to work on my feet, calves and thighs. I felt Dan move onto the bed as he worked my upper thighs. As he worked the inside of my legs his fingers occasionally brushed the head and underside of my cock, which had already began to harden from the porn I was watching. The feeling of that light, teasing touch on my cock had me involuntarily spreading my legs, hoping for more contact.

About this time, I felt Dan get off the bed. I was hoping he would continue and could feel that my cock was fully erect now and on display between my slightly splayed legs. After a minute or so however, he came back to my head. As he stepped up and began on my back again, I saw his legs were now bare! I lifted my head slightly, just enough to see he was completely naked! His cock was only half erect, but looked to be already nearly 7" and very thick. He noticed me lift my head and gently pushed me back down.

On the porn, the girl was in a 69 with one guy and being fucked by the other. The guy 69ing with her was also licking the other guy's balls every few strokes.

As I was watching this, Dan began to work on my lower back and ass muscles. As he leaned over me to reach, I felt the substantial weight of his cock on my shoulder. It felt huge and I could feel the heat of it, moving back and forth slightly as he worked. I had never been close to another man's penis before. Just feeling it on my skin had my cock swollen so much it hurt!

His hands were now kneading my buttocks, which were slick with oil, and he was reaching down between my legs before pulling back up with his thumbs dipping into my ass crack, just grazing my hole. I felt my face flush with embarrassment as I realized I had been arching into it without even knowing!

"You still good?" Dan asked softly.

"Mmhmm" was all I could muster for an answer.

Dan's hands grew even bolder, now rubbing one finger back and forth over my asshole as his other hand continued to knead and spread my ass cheeks. I felt him pour a little more oil on the small of my back, then worked it down my ass again, this time sliding a finger easily inside me and working it gently in and out.

Meanwhile, the guy that had been 69ing with the girl was now being ridden while he sucked the other man's cock. As I watched the sex scene in front of me, I felt a second finger being pushed inside me. Although slightly uncomfortable at first, I soon found myself subtly rocking my ass back and forth on Dan's probing fingers.

Dan then stood up, walking again around to the other side of the bed. I felt his weight on the bed and expected some more rubbing and teasing of my cock, when I felt his hands spreading my ass cheeks. I wasn't sure what I was expecting, but I suddenly felt his tongue give a long, slow lick all the way up the crack of my ass. I lost any hope of control as I moaned and pushed my ass back into his face, amazed at what I was feeling. Dan gave a few more slow, luxurious licks before focus his attention on my asshole, working his tongue in and out as he spread me open with his big hands.

I was so engrossed by Dan's attention that I hadn't noticed what was going on in the porn that I had been watching. One man was now assfucking the other from behind while the girl watched and masturbated.

I was mesmerised by the large cock sliding in and out of the man's ass and I pushed my ass up for Dan as I watched the porn, imagining what it must feel like to get fucked. Dan then removed himself from the bed for a few moments, before returning and this time straddling my legs as he got back on the bed. I felt more warm oil dribbled on my ass crack, followed by a thumb working it in. This oil felt much more slick than the stuff he had started with and his thumb easily pushed into my asshole. I then felt even more dribbled on as he moved his thumb in and out of me.

I groaned in disappointment as he removed his thumb. Dan chuckled quietly and shuffled forward so he was now straddling my thighs. His heavy cock lay directly on the crack of my ass. I felt him pour some more of the slick stuff on my ass and, I assumed, his cock.

"Have you ever been fucked?" he asked me as he slowly, deliberately slid himself back and forth.

"No" I replied, even as I found myself wriggling my butt against his thickness.

He slid back then, grabbing his shaft and pushing the head of his cock down to my sphincter. He pushed gently until my asshole just started to open, then pulled back and again ran it up and down my ass crack. The next probe of his cock was just a little deeper & held a little longer. Each time hurt a little bit, but gradually subsided as I relaxed into it. He repeated this several times, each time adding a little more "oil" and each time pushing a little harder and farther into my asshole. As I felt my ass finally accept the head of his cock, Dan paused and leaned forward bringing his head down beside mine.

"This is it" he whispered into my ear. "I'm going to fuck your ass now."

I felt a tremor throughout my body when he licked the back of my ear lobe. As he held my shoulders and took my ear lobe gently in his teeth, I arched my back into him just as he gave a powerful thrust, driving his huge cock deep inside me.

"Oh fuck!!" I nearly screamed. I'm not sure if it was pain or shock, but I instinctively tried to scramble out from under him. Dan had a firm grip on me though, and pinned me in place with his body weight as he kept himself buried in me and moaned as my asshole convulsed on his cock. As I stated, I had done some anal play with toys before, but nothing as thick as Dan.

"Shh... just relax" he whispered in my ear before nibbling on my neck. This sent more shivers down my back and I arched again. Finally I was able to relax and get my ass to stop spasming around the massive intruder still lodged deep inside of me. When he felt me submit, Dan sat up and ran his hands up and down my back and sides, squeezing my butt.

"Goddamn! You should see this, you look so sexy with my cock in your ass." He slowly pulled almost all the way out and applied more lube before pushing himself all the way back inside me. The pain had almost subsided already and was being replaced with absolute pleasure. He leaned forward again, kissing and nibbling on my neck as he slowly pumped the full length of his big cock in and out of me.

After several minutes of tender, slow fucking, Dan pulled out and got off the bed. I groaned in complaint as he removed himself from inside me, feeling strangely empty without his thick tool stretching me out. He chuckled again and gave me a playful smack on my ass.

"Get on your hands and knees" he said softly. As I did, he guided me back to the edge of the bed so he was standing directly behind me. I again felt his heavy cock rubbing up and down the crack of my ass several times and felt myself pushing my ass back every time the head of his cock passed over my well-lubed asshole.

"That's it" he whispered. He grabbed onto both of my hips and let his cock slip down again until his swollen head was resting on my rosebud. He began to slowly tease the head of his cock just barely in and out of my ass as I tried to push back onto it. Finally he gave a slow long thrust fully impaling me again on his thick shaft.

"Fuck! Your ass feels amazing... does this feel alright? You look absolutely stretched!"

"Yeah. That feels so fucking good."

Holding my hips, he pulled most of the way out and slammed into me sharply, causing me to grunt loudly as his hips smacked into my asscheeks. He repeated this a few times before picking up the pace and fucking me in a steady, rhythmic motion. I was in total bliss, rocking back to meet every thrust, trying to take every inch of him.

Dan then slowed again and ran his hands up my sides and around to my chest, gently pinching my nipples. I had never had my nipples played with, and the sensation caused me to gasp.

"Come here baby" he said, and pulled me upright keeping himself inside of my ass. Wrapping his arms around my chest, he turned my head and said "you're taking my cock like a champ!"

I felt oddly proud of myself from hearing this as I absorbed the feeling of his chest pressed against my back and his arms wrapped around me. Then he kissed me, probing my mouth with his tongue. I was a little shocked at this, but he began to thrust again and I completely surrendered to the feeling of being absolutely controlled. In this position, Dan's cock felt like it was halfway up my torso. As we broke the kiss I noticed the mirror on his closet door almost directly in front of us and I swore I could see my lower abdomen bulge slightly each time he thrust forward.

I felt on the verge of cumming even without touching myself! My cock wasn't even fully hard anymore, but all the sensations had me built up so close to orgasm I thought I could explode at any second!

Dan began to speed up again, thrusting a little harder and breathing heavily. He let go of my torso, dropping me back to my hands and knees, and again grabbed my hips. I arched into him as he began to thrust with purpose.

"Fuck yeah!" he breathed, and slapped my ass a few times as he began to ram my ass harder and harder. The room was filled with the sound of fucking as his pelvis repeatedly smacked against my ass.

"You're gonna make me cum baby!" he exclaimed, "can I just cum on your back?"

"Fuck, please... just keep going!" I pleaded as I pushed back to meet him.

He just growled and smashed his hips tightly against my ass another 5 or 6 times, pushing himself as deep as possible inside me.

"Oh fuck.." he stayed motionless as I felt his cock swell and jerk as he began to cum inside of me. I reached down and grabbed my cock, giving it a couple quick strokes before I began to shoot a huge load out onto his bed. It felt like I kept orgasming for a solid minute and I could feel my ass clenching on his cock as I rocked against Dan while he unloaded into my bowels.

My arms were shaking and I collapsed onto the cum soaked blanket. Dan collapsed with me, keeping his cock inside my well-fucked ass.

"That was incredible" he gasped, "you're a great fuck"

"Thanks" I replied breathlessly as I wiggled my ass into him. "I can't believe how good that felt! Your cock is huge, but it feels amazing..."

We laid like that for maybe 5 minutes allowing our breathing to slow, while his cock softened and shrunk inside of me. As I got dressed, I could feel the cum leaking from my now loose-feeling ass and revelled in the feeling. I paid Dan for the massage and as I turned to leave, he stepped up and kissed me again, giving my ass a squeeze.

"Til next time?" he asked.

I felt so small in his arms looking up at him. " Yes, I... til next time" I stammered.

As I left, my legs felt wobbly and weak. The whole drive home, I replayed the events in my head and by the time I pulled into my driveway I was rock hard... I couldn't wait for next time!!