Escalation

I'd been seeing this older woman for a massage once per week, usually on Sunday at noontime. She wasn't older-older, just older than me. Maybe in her forties. Probably about twice my age. She was pretty, had a decent body for her age. I liked the way she massaged me. She always wore something slinky and see through. She had huge boobs and by the end of the massage she was always naked. She was a little overweight, but not fat. She would get me worked up while I was laying on my stomach, then have me lift my hips. She'd pull my erection down and point it at my feet as she continued to massage me. Then she would tease my cock as she worked me over. After what seemed like forever, she'd have me roll over and stroke me off. After a few times with her, she started to tit-fuck me to orgasm. It was awesome.

We'd talked enough for her to know a lot about me. She knew I was a Naval Officer on a ship stationed locally and where I was from. She knew a lot of other little details about my life as well. Funny, but I didn't know much about her. Except I did know she had a "partner." I wasn't sure if that meant she was a lesbian or not and I never asked.

I didn't have a girlfriend and didn't really want one. I was concentrating on my career and climbing the promotion ladder, so my weekly massage was all the sex I was getting. It worked for me and I had the $200 each week she charged. So, fuck it.

Three times ago with her, she was in the middle of teasing my cock. Then she started doing something that she'd never done: started playing with my asshole. It made me jump out of my skin when she touched me there the first time, but I soon relaxed. She slowly rubbed her finger around my asshole, teasing it. Then I felt a rush of cold massage oil being applied to my hole.

"Can I put a finger in your ass? It's very erotic," She asked.

"Umm...sure," I managed.

"You'll love it, I promise. Just relax and let me do all the work," she said. She moved my legs, spreading them wide on the massage table. Then I felt her climb up on her knees between my leg.

"I'll tease your cock while I finger-fuck you," She said. Her finger traced circles around my asshole while another finger teased my cock. "I'll be gentle. At first, anyway."

I felt her push her finger into me slowly. I let out an audible moan. "Oh, God," I whispered. I'd never had anyone ever play with my asshole. I suddenly wondered why? It felt really good to have her finger slide into me like that.

She pushed in all the way until I felt her knuckles of her hand hit my ass cheeks, then she pulled out again. Slowly, she slid her finger in and out of my while she teased my cock head with her other hand.

"Has anyone ever played with your ass before," she asked me.

I was moaning softly. "Never." I noticed that my hips were moving in time to her finger.

"No?" she asked. "That's too bad. Boys don't know the pleasure that they're missing when they're close minded like that. Doesn't that feel good to have my finger sliding in and out of your ass, Baby?"

"God, yes," I moaned.

I felt her finger slide in all the way, and then she began to rub in circles inside me, toward my cock.

I lifted my head off the massage table. "Holy shit," I moaned. Her fingers continued to rub inside me. I suddenly felt I was about to orgasm and it was going to be a good one.

"That's your prostate," she said. "The male G-spot, some people call it."

Her finger continued to rub it lightly. I laid my head down again and savored the feeling. My orgasm continued to build inside me. I could feel it like a ball in my gut.

"This is one of the most sensitive spots on the male body," she said, calmly talking to me like I was her student. "You're going to cum soon, aren't you?"

Hearing her say the word "cum" sent me over the edge. "I'm gonna cum," I warned her.

"Just let it go," she encouraged. "Just let it happen."

I exploded like I'd never done before. My body convulsed again and again. I felt my anus squeeze down on her finger as she continued to rub my prostate.

Finally, it was over. She pulled her finger from my ass and got off the massage table.

"Tell me that wasn't the best orgasm you've ever had," she said as she wiped the lube off my ass.

"Fuck," I breathed. That was amazing.

As I was getting dressed, she came back into the room in her bathrobe.

"Did that weird you out?" she asked me.

"No, that was amazing," I told her as I fished my wallet out of my pants and handed her her money.

"So, you liked that?" she asked.

"Loved it," I said as I smiled at her.

"Ok," she said and smiled. "Would you like to try a vibrator next time?"

"Really?" I asked.

"Really," she said. "Not a big one or anything. Just a little one that will park right on your prostate. If you liked my finger up there, a vibrator will drive you wild."

I thought about it a second, shrugged my shoulders, and said "Yea, why not?"

"Good, " she said. "But there's something you have to do before you come over next time. You have to use an enema before you come. Get yourself nice and clean on the inside for me so there's no mess. Deal?"

I laughed. "Ok, sure," I sad. We made arrangements for next week and I was off.

All week, my only thought were on her and the vibrator I was about to experience. I constantly had to hide my erection at work. The thought of what was coming consumed my mind.

Sunday came and I did as I was instructed, then headed over to her house. I knocked on the door and she opened immediately. She was wearing her bathrobe as usual. I entered her house and we hugged, which is what we always did. We made a little small talk and then she lead me back to her massage room and closed the door behind us, again as usual. I think she liked to watch me undress because she never left the room when I did. She put on a little light music and I undressed.

"Did you use the enema?" she asked as she dropped her robe. This time, instead of wearing something like a baby-doll or whatever, she was naked. Her large breasts hung low and there was a faint landing strip of pubes below. She looked pretty good, I thought.

"I did," I said as I climbed onto the table, face down.

She began the massage and I relaxed.

"Good," She said. "I really think you're going to enjoy this. It will be breaking and big boundary for you, I think."

"I've been looking forward to it all week," I said honestly.

Her hands roamed around my body, her technique relaxing my muscles. The anticipation was killing me.

Finally, she had me raise my hips and she pulled my cock down. I spread my legs wide without being told to. She climbed up onto the table without a word.

"Here comes the fun, honey," she said as I felt the cold massage oil being poured down the crack of my ass. I felt it flow over my anus and down over my balls. She smeared it around my cock and balls and then up to my ass. It felt like she used a gallon of the stuff.

She teased my hole with her finger and the head of my cock with her other fingers. "So, you've been looking forward to this, have you? Having me use a vibrator on you?"

"Honestly, " I said. "It's all I've thought about all week."

"Really?" she said. "I think someone likes it back here." I felt a finger enter my asshole. "I think we have found someone who likes the Greek way as much as I do."

"You like it back there, too?' I asked.

"I love it in the ass," she said. Her finger found my prostate and she started to tease it. I moaned.

She continued to tease me for a while, and then she pulled her finger from me.

She climbed off the table. I lifted my head and watched as she opened up a cupboard in the corner and turned around. She held the vibrator toward me so I could see it. It was neon green, had a silver base, and was about 7 inches long. It wasn't that big around though. I watched as she rolled a condom onto it. I laid my head back down.

I felt her pour more oil down my ass crack and she spread my cheeks. I jumped when I felt the vibrator slide up and down my ass crack, from my balls to my anus. Up and down slowly, she slid the vibrator, teasing me. Then I felt her lay it lengthwise down my crack and she released my cheek, leaving vibrator humming away with its tip against my balls and the rest just resting along my taint. It felt unreal.

"How's that?" she asked softly as she massaged my glutes.

"Really good," I breathed.

Her hands worked over my glutes and my hamstrings. After a few wonderful minutes, she removed the vibrator and had me turn over.

"Lift your left leg up so your knee's on your chest," she told me. I did so and I watched as she smeared more massage oil over the dildo. "Just relax," she said as she moved closer to me.

I could hear the dildo vibrate, then she started to slide it up and down my ass crack again. I could feel that my nether regions were wide open and ready.

"Oh my," I breathed.

"Feel good?" she whispered.

"God, yes," I breathed.

"Good," she whispered. "Here it comes."

She pushed the dildo into me with little resistance. I felt it vibrating inside me. It felt amazing. She had me lower my leg, but spread them as wide as I could. She slowly slid the dildo in and out, in and out. Then she took my cock in her left hand and stroked it in time with what the dildo was doing. She kept her pace slow, edging me. When she sensed I was getting close, she would stop stroking me. But she never stopped sliding the dildo in and out of me Time stood still. Over and over, she would bring me close to orgasm and then back off. I was moaning loudly. It was heaven.

"Have you had enough yet?" she asked. "Are you ready to cum?"

"Yes, please, let me cum," I begged.

"Are you sure? Don't you want this to last forever?" she teased.

"Please? Please let me cum," I begged.

"Call me 'Mistress'," she said.

"Mistress, please....please let me cum," I begged.

"Good boy," she said and started to stroke my cock faster. "Raise your head so you can see yourself cum."

I did as I was told and I watched her hand move up and down my cock.

"Open your mouth," she said in a commanding voice.

I did so.

"I want to see if I can make it shoot in your mouth," my new Mistress said matter-of-factly.

I watched as her hand stroked me. The vibrator was doing it's thing on my insides. Her hand stroked quickly and firmly. The orgasm built up inside me. There was no stopping it.

"Oh, God," I moaned. "I'm gonna cum."

"Open wide," she commanded as she aimed my cock at my face. She pushed the dildo deep into my ass and left it there.

I watched as my cock started to spasm in her hand. A jet of white exploded out of the tip and shot toward my face. I closed my eyes as it splashed onto my right cheek with some force. It was hot on my skin. I felt another ribbon of cum splash onto my chin, barely missing my mouth. Ribbon after ribbon of thick cum splashed onto my chest. She continued to stroke my cock until the wave subsided. The dildo continued to buzz away inside me.

When I'd finished, I laid my head back down on the massage table. I was breathing hard, light sweat was forming on my skin. I felt her remove her hand from my cock and wipe my cheek with a finger.

"Open up, sweetie," she said sweetly.

In a post-orgasmic haze, I opened my mouth. I felt her finger slide into my mouth and I closed my lips around it. I could taste the distinctive taste of my own cum fill my mouth. Her fingers continued to scoop up the remainder of my load from my chest and stomach and feed it to me. I didn't care. I was still in heaven and the dildo was still going like mad inside me. I'd never felt anything like that before.

I felt her breath on my right ear as she whispered "Good boy." Then she removed the vibrator from my ass. It was if I could still feel it inside me. I opened my eyes in time to see her close the door behind her as she left. I got up and started to get dressed.

As I was tying my shoes, she re-entered the room, in her bathrobe as usual.

"Well, what do you think?" she asked.

"That," I said, "Was plain awesome. We're doing that again."

"Oh, good," she said, smiling broadly. "I like to break boundaries. You're very open minded, did you know that?"

"Well, I try to be," I said.

"Actually, you're my only steady client. I'm getting older now and age is a limiting factor in this line of work. Can I ask why you keep coming back to me?"

"Well," I said and then I paused. Why did I keep coming back? "I guess it's because I'm used to you. I feel better after I've been with you, you know?"

"I do know," she said. "And I know why, too. You feel better after I've finished with you because you open up yourself to me. There's power in this relationship. You allow me to push your boundaries. I get to feel your young body in my hands. It's good for both of us. You're like putty in my hands to do with what I will. While I'm the more dominant one, you have all the power because you can just choose to not come back any longer. I love that you call me 'Mistress' now. It makes me feel young again. I want you to continue to call me that. Understand?"

"Yes, Mistress," I said.

"Good boy," she said. "See you next Sunday noon?"

"Yes, Mistress," I said.

"You'd better be here on time, or you'll be punished," she said.

"Yes, Mistress," I said. "I will be here at noon sharp."

"We will be trying something new next time," she said very matter-of-factly. "Do you know what 'pegging' is?"

"No, Mistress," I said.

"Pegging is when I use a strap-on dildo to fuck you in the ass," she said. "Does that appeal to you?"

I paused. "I'm not sure," I said.

"Well," she said and she opened her bathrobe. Underneath, she wore a black leather harness on her hips. Sticking out of front was a flesh-colored cock, about 8 inches long. "This is what you'll expect to have, if you choose to show up on Sunday. If you come to me, I'll know that this is what you want. If you don't, I understand and I hope you have a great life because you will no longer be allowed in my house." She reached down and started to stroke her fake cock. "It's either this, or nothing. Remember: you have the power in this relationship. You can choose to come or not to come." Then she closed her robe around her waist.

"Yes, Mistress," was all I could think of saying.

"You'll use an enema again before you come," she said. "And you may not masturbate at all. I'll know if you do. No matter how turned on you get. No matter how much you think about me and my cock sliding into your ass, you are not to touch yourself. Do you understand?"

"Yes, Mistress," I said.

"Good boy," she said. "Now... go home. I'm finished with you for today." She opened the door and lead me out.

Let me tell you something: That was the longest week of my life. I couldn't concentrate at all on work. I had an almost constant erection. I could think of nothing besides Mistress and her cock and what she had planned for me. It consumed me. When Sunday morning came, I could barely contain myself. I wanted to get into my car and drive to her house at nine in the morning and just wait outside. I used the enema as instructed at eleven o'clock and then drove over to her house. She lived in a busy area of University Heights. It was always a pain in the ass to find a place to park.

I knocked on her door at 11:56. There was no answer. I knocked again. No answer.

I stood there wondering what I should do now. I stood there for a few minutes. As my watched beeped noting that the hour had struck, the door opened in front of me.

"Good afternoon, my good boy," Mistress said, smiling broadly. "I'm glad you're here. Would you like to come in?"

"Yes, Mistress," I said.

She stood in the doorway wearing her bathrobe.

"Take off your clothes," she said.

"Take off my clothes?" I asked. "Here?" I looked around. There were easily 20 people within sight of me, going about their business.

"Did I stutter?" she asked and crossed her arms across her chest.

"No, Mistress," I said.

"Then take off your clothes," she commanded.

I stood there for another second and took a look around. No one was actually looking my way. I looked back at her.

"If you want what I know you do, you'd better start stripping," she said.

Fuck it, I thought and started to strip. When I was finally naked, standing in her doorway, my clothes in a pile at my feet, she just looked at me. Seconds ticked by and she just started at me. Then she stepped aside and allowed me to enter.

She closed the door behind us. "I was hoping that there would be more people outside. Maybe one of my neighbors. I'm sure that they'd get a kick out of a naked young man on my doorstep. Especially my neighbor across the street. He's quite flamboyantly gay. I'm sure he'd love to get a look at you." She walked by me and lead me to the massage room. "Maybe next time, " she said as we entered.

"I think a little humiliation is good for a young man like you," she said as we entered the massage room. "It will keep you inline. Don't you think?" She opened her robe and I got a good look at her. She was wearing a red push-up bra that only had the bottom half of the cup, leaving her tits seriously jutting out over the top. She was also wearing her black harness with the fake dick sticking out of it. I watched as her hands slowly moved from her tits down her chest to her cock. I was mesmerized as she slowly stroked it.

"Is this what you're here for?" She asked.

My mouth was dry. I croaked "Yea, Mistress."

"Good," She said and pointed at the table. "Get on your stomach."

"Yes, Mistress," I said. I began to wonder just what the hell I'd gotten myself into.

She began her massage. I instantly relaxed.

"So," she said. "Have you been thinking about this all week?" Her hands were rubbing my muscles. I was indeed putty in her hands.

"Yes, Mistress," I said.

"Have you been thinking about me pegging that tight little ass of yours?"

"Yes, Mistress," I said.

"You have a lovely, round ass," she said as her hands rubbed my butt. It felt wonderful. "I'm really going to enjoy this. I think I may get more pleasure out of it than you will, to be honest. But that's what being your Mistress is all about. Your pleasure is secondary now. You pleasing me is all that matters. Do you understand?"

"Yes, Mistress," I said.

"Good boy," she said as she grabbed my ankles and spread my legs wide. "We'll start slow, I think. Just a little light play. Then we'll move on to the more intense play later. Is that ok with you?"

"Yes, Mistress," I said.

She had me lift my hips and she pulled my erection toward my feet. I felt the massage oil being poured down the crack of my ass. Her hand smeared it around my cock and balls and then she rubbed it around my anus. I moaned when she touched me there.

"You're such a little ass-slut aren't you?" she teased. "You'd like nothing more than a finger or two in your ass right now as I tease your little cock, wouldn't you?"

"Yes, Mistress," I moaned, barely a whisper. What the fuck was I doing?

Her finger traced circles around my anus, teasing me. Her other hand was slowly teasing my cock head.

"Did you like it when I fed you your own cum last week?" she asked as she pushed a finger into me. "Do you enjoy the taste of it? The feel of it on your tongue? "

I didn't answer. I just laid there reveling in the feelings that were coursing through my body.

"I bet you did," she continued. "I bet you loved it. You're a little cum-slut, but you just don't know it. Well, my little dove, I'm going to show you that side of yourself. I'm going to bring my little boy's dark side out. You're going to do whatever I say, aren't you?" Her finger found my prostate. I shuddered. Bolts of lightning ran through my body.

"You're mine to play with now," she continued. "But remember: you have the power in this relationship. You can end it anytime you'd like. You just have to tell me to stop and I will. Then we'll say goodbye and never speak of this again. You can go your way and I'll go mine. But as long as you keep coming back each week, we're going to up the ante each time. Is that ok?"