Massaged Inside and Out

This is my first story submission on Literotica. Comments, critiques and feedback are welcome. Please feel free to let me know how I can improve my writing. This is a fantasy, all characters are fictitious, and over the age of 18.

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I guess I should have realized that something like this would happen eventually. I was always made fun of in school for having a "girly" build. At only five foot 4 inches I'm not particularly tall. I have slim shoulders, thin arms and legs and my hips are probably more shapely than most guy's. I didn't exactly help things by keeping my blonde hair shoulder length. I told everyone it was because I liked metal music. Most of all though, I apparently have a nice ass.

The shower room in gym class was pure torture, guys would always be trying to sneak a peek at it or touch it or giving me dares to shake it. I got constant pinches and gropes in the halls. I even overheard the popular girls, the ones who didn't normally even acknowledge I existed, saying how they wished they had an ass like mine.

I thought all that was behind me when I finally finished high school and got my IT certification. I had an adult job, away from all the posing and bullying that kids are known for. Hell, I was working with other people who, for the most part, had been on the receiving end of bullying themselves, so they generally would understand. And for the most part they did. I got a few stares, even had one guy try and chat me up until I turned around and he realized I was a guy. That all changed on the day I decided I needed a massage.

It was only a few weeks after I started at a new company. I've never had particularly good posture, and a good office chair that would keep the worst of the consequences of my slouching at bay was still on order. By the end of the first week my back was killing me. I could barely walk around the office. I figured a massage would be the best way to get back on my feet quickly. I booked an appointment with a place a coworker recommended over the phone and went in the next week.

As I limped inside I was greeted at the door by a tall redhead, who's name tag read "Elizabeth."

"Hello! You must be Adam. We just need you to fill out a few details here, and we'll get you in right away." she said, handing me a small clipboard and pen. Elizabeth was an absolute knockout. Standing at least five foot ten with legs that seemed to go on forever, she stared down at me as I started filling out the forms. It was difficult to keep my concentration, as her breasts were actually sitting virtually at eye level with me. I swallowed hard and Elizabeth smiled knowingly as she turned to give me some space. Looking closer at the forms she had handed me I quickly filled them out until the last question.

"Would you prefer a: Female masseuse, Male masseuse or Doesn't matter?" it read. As usual when confronted by a dizzyingly beautiful women my brain went into overdrive thinking about how to act. This never really works out as I always end up over thinking and screwing it up anyway. My record with women was extremely, and I'd never managed to be with a woman as drop dead gorgeous as Elizabeth. "Would she think I'm a pervert if I check female masseuse? Would she think I was gay if I check male masseuse?" I finally decided on "Doesn't matter." Thinking logically, knew I didn't have a chance with a women like Elizabeth and I figured I'd just take whoever was available first and be out of there quicker. I went up to the counter and handed her the clipboard.

She scanned the forms for a second and when she reached the bottom I swear I saw her eyes light up and a small smile creep across her full red lips. "Right this way Adam" She said, with a great deal more enthusiasm than when she had greeted me at the door. I was just thinking maybe I might have done something to entice this earthly goddess when she showed me through a door to a small room and said "Dale will be with you shortly, please strip, cover up with one of these towels and hop on up on the table." My heart sank. Dale. A guy. Shit. I hadn't even considered the possibility that checking "Doesn't matter" might actually result in a male masseuse. How many of those even existed? I wasn't really prepared to be handled by a guy.

"Oh well, might as well get it over with. It's just a massage. Might be a bit awkward but I'm here for a reason, right?" I started trying to convince myself as I stripped.

Just as I was covering myself with the towel I heard the door open. My back was to the door and as I turned I heard a deep male voice say "Oh, I'm sorry ma'am, I must have the wrong room." When I turned to face the door I saw a big man, standing at least six foot three and built like a linebacker closing the door. His shaven head disappearing, apologetically dipped toward the floor.

"A-Are you Dale?" I managed to ask before he had fully retreated.

The door stopped. "Oh... Oh man I'm sorry. You're Adam right?" He said as he started back through the door.

"Y-yeah." I couldn't help but stare. Dale was huge. His hands could probably palm a basketball, his head nearly brushed the door frame as he came back into the room. Not only was he tall and big, but his arms and legs were well muscled. He clearly did quite a bit of exercise as a hobby or something.

"Look... I'm sorry I said ma'am as I came through. Please don't be offended."

"None taken" I tried to say confidently, failing and having it come out more as a squeak. I was definitely intimidated by this boulder of a man, who was apparently going to be the one working on me.

Dale smiled at my reaction. "Alright then, if that little faux pas is behind us, lets get to work. Hop on up on the table and we'll set you right." I did as Dale asked, climbing up on the table, which was set a bit high. Between my back and the height I ended up letting my towel slip as I got up. My face, and presumably other parts of me, turned bright red. "Nothing I haven't seen before man, no need to get worked up over a bit of a slip." I laid down with my face in the comforter, still bright red.

"Alright, you said you're having back problems, probably from sitting at work, right? We'll start with a total back massage with some oil to loosen you up a bit, then get some deep tissue massage going in your lower back and buttocks. How does that sound, Adam?"

"Sounds good" I returned, feeling a bit more relaxed. Dale's professional tone and demeanor were starting to put me at ease.

As Dale started I could feel weeks of stress fall off in seconds. His big hands and strong fingers worked my back like it was dough. Easing the muscles and teasing apart the little knots that had built up. The oil he was using definitely wasn't just normal oil either. The scent was both relaxing, yet oddly musky. And it seemed to be helping my back to relax even more than his skilled massage would normally.

Within ten minutes I was a blissful pile of mush. Completely relaxed under Dale's adept hands. "Alright Adam, we're going to start on your lower back and butt now, okay?" I could only mumble some lightly affirmative gibberish in return. I felt my towel being drawn back, and at the same time I thought I heard an appreciative noise coming from Dale.

"H-hey, wait. Towel..." I tried to voice my concern at being basically naked in front of Dale, but could barely get out any more words before I felt his solid hands go to work on my ass.

"Don't worry man. I do this all the time. I can't work those deep muscles in here through the towel, and man does it feel tight back here." I could almost hear the smile on his face, but couldn't object any more because his hands were making me feel incredible. Dale started moving back up to my lower back, and with that I was once again totally under his control.

A few minutes passed in silence as Dale worked the worst of the tightness out of my back. It was incredible. Each of his massive hands could cover most of my back, yet his fingers didn't feel clumsy at all. Exactly the opposite, it felt like they could tune each individual nerve in my back exactly the way they wanted. I was complete putty in his hands. Very slowly I noticed Dale paying more and more attention to my ass. And not really massaging it like he was before, more stroking and kneading it. Like the groping I experienced as a teenager. I was in no real state to object, since it felt nice, and he had been completely professional up to that point.

A little more time passed and I felt Adam stroking between my cheeks as well. I felt more oil being poured, this time directly on my backside. As it slid down between my cheeks I felt it flow over my asshole. I twitched a bit at that, but still didn't object. I heard Dale groan as he started back in on my cheeks. I tried getting a look at him behind me, but couldn't really turn much without disturbing his hands working my ass. They still felt incredible, but it was starting to be in a different way.

Dale's hands were creeping lower and lower on and between my cheeks. My relaxed brain was still just starting to feel that something was wrong when Dale's fingers first brushed my asshole. It felt like I had been shocked. No one had ever touched me there. And I suddenly shifted.

I immediately felt one of Dale's big hands on my shoulders holding me down. "Wait a minute man." Dale said, he sounded a bit out of breath. "Don't go anywhere just yet, I'm not done here." I stopped trying to get up. I couldn't say a word to that calm tone. Or ridiculously strong hand holding me down. When I relaxed Dale went back to work, this time more focused on my asshole.

As Dale worked on my ass again, he simply worked on of his big fingers around the outside of my hole for a few seconds. Then went back to stroking my cheeks. After a few seconds of that the finger would return to my hole. He'd stretch my cheeks open to expose it, then let them slap back together. Without meaning to I started to both relax and become aroused. The entire situation had put me in an extremely open mindset. Dale's strong confident demeanor, as well as his magic hands made me trust him. The massage and oil had me relaxed. I couldn't object. Until he tried to probe my asshole with one of his massive fingers.

"Hold up. Wait. I'm not gay man." I said, this time managing to gather a bit force behind my objection. "Look, I'll just get dressed and pay. I won't say anything and we'll put this behind us, okay? You're massage was great but I'm not really into a "happy ending" or anything..." I trailed off as I got my shoulders off the table and turned to look at Dale.

Dale at some point had taken all his clothes off. I have no idea how he stripped without me noticing, but his cock was out and hard as a rock. It was at least 8, maybe even 9 inches long and thick. He had a wide smile on his face. "You aren't leaving just yet. Like I said before, I'm not done back here yet." He punctuated the "here" with another finger on my ass. And his other hand went to my shoulders to hold them down. "Look at you. Tiny little thing walking in here with an ass like this." He spanked my ass, eliciting a squeak from my throat. "I bet you requested a male masseuse just to tease them." He spanked my other cheek at that, I could feel my cheeks redden as they shook. "Umph. I know women who would kill someone for an ass even half this good and you're telling me you don't like dick? It's a waste I tell you." He slapped my ass again. This time I could only groan. He stopped spanking me and went back to probing at my asshole with one finger. This time much more focused.

I don't know what it was. Maybe I was scared of Dale. Maybe I was just that turned on. But I didn't yell for help. I just accepted whatever Dale was going to do to me. "Yeah thats it, relax. This goes way easier if you relax." I could feel my hole relaxing more and more at Dale's careful ministrations. I could also feel my own cock start to grow under me. "Haha, now we're getting there. You're liking this, I'm liking this. We'll have some fun together. But I don't like guys either. So I'm going to call you... Amanda from now on, got it?" I could only moan in agreement as Dale punctuated his question with his finger finally entering my hole.

"Oh thats tight." Dale commented as he slowly pushed his finger another fraction of an inch inward. I felt more oil being poured between my ass cheeks as he slowly started moving the first knuckle of his massive finger in and out of my asshole. It felt like nothing I'd ever felt before. It felt both like a filling sensation and a bit painful, but also pleasure at the friction around my opening. I was going crazy at just one knuckle of one finger.

"Heh, you're pretty sensitive back here. Body built for sex, huh Amanda?" I couldn't say anything in response as Dale sunk his whole finger into my ass. "This is going to take a while to get you loose enough, and I need a bit of... release if I'm going to enjoy this to the fullest." Dale pulled his finger out of my ass, leaving a feeling of emptiness. I couldn't help but admit I wanted it back in there, I caught mysel involuntarily moving my ass around looking for the missing magic digit. I was interrupted by Dale standing in front of the table at my head. His erect cock right in front of my face. "Suck it while I get you ready for the main course.." I hesitated. His dick was huge, with one prominent vein running the length of his tool, throbbing in time with this heartbeat. I could feel the heat of it on my face. I looked up at Dale. He was smiling down at me. "Oh, do you not want to continue now?" His long arms reached across my tiny frame and I felt him finger my asshole again. I couldn't help but shift my hips, trying to get him to put it back in. Suddenly his finger retreated again. "I could stop right now too though. Just like you asked. You could get up, get dressed and go pay. Or you could put my big rod in your mouth and suck it like a good girl, and I'll keep getting you ready for the main course." I stammered wordlessly. I couldn't believe I was even considering sucking a man's cock just so he would put his finger back in my ass. "Well slut? What do you want?"

I hesitated again. Things were going too fast. Was I actually gay? I didn't think so, but then again I had a cock inches from my face and just had a dudes finger up my ass. What I did know is that I wanted more of what I just felt. And I was willing to do nearly anything to get it.

"... I-I'll do it"

"What? What are you going to do?" Dale returned, his smile widening on his face

"... I'll suck your dick." I breathed.

"Sorry? Didn't catch that."

My face turned bright red again. "I... I-I'll... I'll suck your cock! Just, please, finger my ass more!"

"Thats more like it, a slutty body should have a slutty mouth too." He briefly leaned down and whispered in my ear "You look even more like a girl when you're embarrassed too." I couldn't help but shudder as he straightened back up bringing his hard meat back to eye level.

I still hesitated but Dale made no move to touch me. He just stared down at me with that smile on his face. Meanwhile my ass was starting to itch with the need to have something inside it again. I looked back at Dale's hardness filling my view. It was, if anything, even more intimidating than the man it was attached to. Its length was frightening, its girth even more so. And yet I was starting to appreciate its masculine beauty. I finally scooted closer and kissed just the tip. Eliciting a gasp from Dale. Taking that as my cue I parted my lips and let it slide inside. The head was soft. Softer than I expected. He tasted of sweat and cum. I let my tongue swirl around the head, just to see how he would react. "Holy shit." He groaned in appreciation. I felt Dale shift and go back to fingering my needy asshole. At the instant he slipped his finger back inside I groaned around his shaft and he slipped further into my mouth. "Start moving slut. You're doing good for a first timer, but if you want more back here you've got to work down there too." I groaned again at his words. Calling me slut and a girl was starting to turn me on almost as much as his finger.

I got to work on his cock. I bobbed my head as much as my position would allow. The hard shaft had a different texture than his head, smoother but just as good. I tasted his precum starting to leak from the tip as I went deeper and moaned at the salty taste. I worked my tongue along the bottom of the glans, just the way I liked it. Dale moaned again in appreciation and started to work the finger in my ass in tight circles.

"Hold on slut I think you're almost loose enough for two." Dale said from above me. I barely heard him. I was focused on the fingers in my ass and the hard shaft in my mouth. The smell of his cock was intoxicating and I caught myself wanting more in my mouth. "Alright, here's number two back here, and a bit extra down there." Dale chuckled as I felt my ass being stretched around a second finger and he started sawing his cock in and out of my mouth at the same time. I groaned around his shaft again.

Dale started to get a rhythm. As he pulled out of my mouth he would push his fingers into my ass. As he pulled his fingers out of my ass he would fuck my mouth. "Oh man this is too hot, you're a real talent now that I've got you going, I think you're ready for three." As he pushed the third finger into my ass he also hit the back of my throat. The groan that ensued let him slide right in. Now Dale was fucking my face in earnest. With long slow strokes Dale slid past my lips as I maintained suction. He slid past my mouth, into my throat and bottomed out. My nose pressed into his close cropped pubic hair and his balls rested on my chin. He held it there for a second that felt like an eternity, then, just as slowly pulled it back out. I couldn't help but run my tongue along the shaft and tickle his head as it went back out. The fullness in my ass and the cock in my throat were starting to feel right. I was enjoying being facefucked and fingered at the same time. Maybe I was gay, maybe I was just submissive or a sissy. At that moment I didn't really care, I just wanted Dale to use me however he wanted. Dale was starting to speed his facefuck up, and losing rhythm in my ass.

I knew what was coming.

"Oh fuck. This is too good. I can't take this shit." Dale was speeding up, getting too fast and hard for me to handle. He suddenly rammed his full length into my throat and held it there. I couldn't breath, I started gagging and feeling short of breath. His balled tightened on my chin. I felt his shaft pulse once, then twice, then Dale started pulling back as his shaft kept pumping my throat full of cum. When his head reached my mouth he laid a big load on my tongue. The taste was incredible. Salty and masculine. I knew I wanted more of it. He pulled out of my lips with a satisfying pop and still had enough in him to unload one last time on my face. Without thinking I swallowed the cum in my mouth. I started to wipe off the cum on my face when he stopped me. "No. You look just slutty enough with cum on your face. You'll leave it like that." I didn't even question him at this point. I was totally his.

Incredibly he was hard again in only a minute. "I've been on a bit of a dry spell the last few weeks, and working with that bitch up front has me under a lot of pressure, if you know what I mean. You're the perfect opportunity to blow off some steam" Dale explained as he moved to the side of the table. Without warning he grabbed my ankles, spun me sideways and dropped them, so I was presented doggy style on the table for him. "Oh that is a perfect view. This ass is something else." He laughed as he spanked my ass again, I couldn't help but wiggle it a bit in both appreciation and anticipation.

Dale spent a few minutes kneading my ass cheeks again. I heard him crack the bottle of oil and pour some on his delicious shaft. He then brought his head up to my hole. I couldn't believe it, but even after having had the thing in my throat it still felt even bigger pressed up against my virgin asshole. It felt massive. I was getting nervous again when Dale circled nearly my whole waist in his massive hands and put some pressure on my hole with his cock. I groaned in pain as it started to force its way into my passage. The huge head was like a battering ram. "Shhh relax. Dale will take care of his little girl Amanda. Push out for me Amanda." I did exactly as he asked, not even slightly perturbed at his insistence on calling me by a girl's name, and the head popped in. I practically shrieked in both pain and pleasure. Dale waited a few seconds, then, with slow circles of his hips, started pushing his shaft in. It felt like wave after wave of cock. Slowly my ass opened, heated up with pain, then cooled into pleasant fullness. He kept pushing, slowly, steadily until I felt his hard pelvis press against my soft ass, and the light down on his balls tickle my own testes. He was all the way in.