Jim's Discoveries Ch. 02 - Susan

I said, "Well, that was quite a surprise. Don't you think you should tell someone you're going to do that?"

Susan laughed and said that expected vs unexpected would get a different reaction, and she wanted to see how I would respond, if I didn't know she was going to do it. "It seems to have had exactly the effect I was going for," she said.

She went on to explain that the reaction was different for pleasure that was expected vs. versus pleasure that wasn't. "Think about the difference between last time and this time. This time you knew I was going to jerk you off at the end of the massage, but last time, every touch was something new and unexpected."

It made sense, and she reassured me that enjoying anal pleasure didn't mean I was gay (this was the early eighties - the thought was terrifying for a lot of men, especially young, naive ones, like I was). After all, she said, she was a girl, so if a girl had her finger in my ass, it couldn't be gay. She had a valid point, and the one thing I knew for sure was that it felt amazing, especially when she was working on my cock at the same time.

I toweled off the oil and cum as best I could, got dressed, and told Susan that I was going to shower, but that I would like a drink, and that if she wanted to go have one with me, I was buying. She said that sounded good, and that she needed one, too, so she'd be over as soon as she was dressed again.

I hadn't been out of the shower long when Susan came in. She asked how I was. I said I was still trying to wrap my head around the finger in the ass, but I felt great. I asked if that was part of a normal massage. She said that not everyone offered it, and not all clients wanted it, but that many did, so it was suggested she try it on me. Susan was pretty sure that it would catch me by surprise, and it did - she wanted to see my honest reaction to it. She also said that she didn't know how many more sessions we would have before she started seeing clients, if any, but she didn't think there would be many more. I said I understood, but I had to admit I was bummed.

She went on to say that Andy knew I was being her practice partner. I was at a loss for words. She said not only was he cool with it, but it had been his idea. When she originally approached him about the massage job, he wasn't thrilled, but admitted he'd gotten massages that ended with a handjob and even with a blowjob, and that he was okay with her doing that, as long as she didn't fuck her clients. Before I could ask, she said that there were a few special clients who were regulars that had been going to the same girls for years, and most of their sessions ended with a fuck.

She had assured Andy that wouldn't happen, which made him happy. She told him she was supposed to practice on someone, but he was a thousand miles away.

Andy had said, "Well, what about practicing on Jim? Do you think he'd be cool with it?"

Susan told him that she was pretty sure I would be, and that she thought most guys would be not only okay, but ecstatic to be getting a no-strings-attached handjob from a naked woman. It was tough to argue with that kind of logic. Anyway, Andy said he thought I was a safe person to practice on, not only because I was a friend and a neighbor, but because I was a decent guy, and I didn't have a girlfriend, which would have complicated things.

As promised, I took her to a nearby bar for a couple of drinks before calling it a night. She thanked me for the drinks, and I thanked her for her earlier efforts. She grinned and said goodnight, leaving me to try to make sense of everything that had been said and done earlier.

The next few days were just business as usual. We'd run into each other coming or going from our apartments, we'd engage in the usual friendly bullshit, but had no further discussions about the previous, or possible upcoming, sessions. On about the fifth day since our last session, I saw her as I was coming in from work and asked her if she wanted to stop by for a beer. She readily accepted, and followed me in.

Over a beer, I asked how the training was going. She said she thought it was going well, but that the subject had come up about offering blowjobs at the end of the sessions. Her trainer told her that they weren't offered to all clients, and that giving the client head would result in a bigger tip. She said that the house got a split of the massage fee, but extras, including being fully nude, giving a blowjob, etc. was agreed on by tips, and those were one hundred percent hers.

"What is it about blowjobs? If my hands are warm and I have plenty of oil, isn't that just as good, or do you guys seriously have to blow your load in a girl's mouth?"

I asked if she disliked giving them, and she said she didn't, but that she didn't like the idea of doing it all the time. I told her that I really couldn't answer her question, because I'd never gotten a blowjob.

"WHAT??? You've never gotten your dick sucked? Have you ever eaten a girl's pussy?" When I said I hadn't, she asked how I learned to give her pleasure to the point of making her cum. I explained that before I moved here, an older woman and her husband (no names or relations mentioned) took me into their bed and between what they demonstrated and what they had me do, I learned a lot.

"How many times did they do that," she asked, clearly intrigued.

"Just once," I said, "but I fucked her twice that night."

Susan couldn't believe that I had learned so much from one encounter, or that I had retained it well enough to pleasure her that well. I told her it was simple - I was extremely interested in the subject matter, so I paid close attention. She smiled and said it was very apparent that I was an excellent student.

She let the topic die, but after another beer, she turned the conversation to the sessions. "It looks like there will be two more. We should do one tomorrow if you're free after work, and then the last one on Monday. If that last session goes well, they're going to have me see clients by myself."

"Have you been seeing them with your trainer?" I asked.

Susan said that she had, and that she had started out watching a hidden camera feed, but more recently, she had been in the room with her trainer and the client. She said that it was a little uncomfortable at first, partly because she was the only one with clothes on.

After the first two she observed, she undressed when the masseuse did, and stood on the other side of the client while her trainer jerked him off. She said the client was fondling her tits and her ass while he got his handjob, and that when he came, it sprayed all over both the trainer's tits and hers. She said it wasn't ropy like mine, but droplets that went out in all directions. Afterward, the guy was rubbing it into her tits and the trainers, which she kind of liked.

I asked her if the trainer had sucked a client's cock or fucked one while she was there, and she said that she hadn't. She said the trainer isn't one of the masseuses that ever fucks clients, but she was supposed to be in a session in a couple of days with a long-time client, so she wouldn't be surprised for it to end in a blowjob.

I don't remember when it was during the conversation, but I realized that my cock had completely stiffened, as we were discussing her activities. I told Susan that the conversation had made me horny, and that I wanted to jerk off.

"But we're going to have a session tomorrow. Are you sure you can't wait until then?"

I said that I could wait, but didn't want to, and that even if I jerked off, I would be ready to go tomorrow.

"I guess we could always move it up a day if you want. Go shower without masturbating. I will do the same thing. Come over in a half an hour. Sound good?"

I said it sounded great, and we slammed the last of our beers and she headed next door. I headed straight for the shower, making sure I lathered up my still-hard cock without stroking it. Remembering our last session, I paid additional attention to my balls and my ass, even easing a soapy finger slightly into my asshole to make sure I was clean, in case she fingered me again. It started to burn slightly before I was able to rinse the soap off completely - something I'd experienced before when I had gotten soap into the opening of my dick.

I dried off, dressed, and headed next door, my cock not full-mast, but not completely limp, either. Susan answered the door in a robe. She closed and locked it behind me, and as she walked into the living room, I noticed she had on black nylons. So much for my cock not being hard. Susan noticed the growing bulge in my shorts and grinned. She said this session was going to be a little different; that the purpose of this session was to further my education. With that, she untied her robe and let it fall to the floor. She was naked, except for the thigh-highs and a matching garter belt.

"Jim, this isn't a massage session. I'm going to continue the education that that other woman gave you. From what you told me, you were a great student, so this is a one-time-only opportunity to learn more about how to be a skilled and considerate lover. I'm fairly sure you'll enjoy it. Do you want to continue?"

Between the gorgeous sight before me and the promise of a memorable night, I was immediately hard again, my cock straining at the basketball shorts I had on. I was at a loss for words, merely nodding my head rapidly.

"Slow down, tiger. I appreciate the enthusiasm and I'll take the vote of confidence, but if you're going to get more than just an orgasm out of this lesson, I need you to take your time and pay attention. Okay? Why don't you get comfortable, and we'll get started."

As calmly as I could, I peeled off my shorts, and my shirt. Since I was just going next door, I hadn't bothered putting on shoes, so I was now completely naked. Susan came over to me and took my hands.

"I know the other woman fucked you and taught you how to use your hands. I want to show you how you can work with your mouth. Let's head into my bedroom. The massage table is great for some things, but most sex happens in bed, so let's go there. Besides, it's bigger."

She led me into the bedroom and stood in front of a big mirror. She told me to stand behind her and wrap my arms around her. I did as I was told, but I tried to hold my hips back, as my cock was going to poke her in the ass. She could tell what I was doing and pushed her ass back against me.

"I know your cock is hard for me. It's okay. It turns me on. Just don't put it inside me. Let it ride up my ass crack. Mmm...it feels nice. Now, kiss me on the back of my neck. Softly. Yeah, just like that. Move your mouth around a little. Put your hands on my tits. Cup them, then gently squeeze my nipples between your thumb and index finger. Ooh, yeah, very nice. Did she have you suck on her tits?"

I told her that she did, but that I could suck on hers if she wanted to make sure I did it right. She laughed and turned to face me, and as she did, she leaned her left nipple towards my face. I kissed it, gently circled it with my tongue, then took it into my mouth, softly sucking on it. Susan moaned her approval, and I began to increase the suction. Her nipple was hard in my mouth, and I flicked it with my tongue as I sucked. She pulled it and offered her right one to me, and I resumed my actions.

Although her moans continued, she pulled away and lay on her back. "You do that well. Now, I want you to slowly kiss your way down my stomach. Yeah, that's good. No, not yet. Keep going down my leg. Once you get to my knee, move to the inside of my leg and work your way back up. When you get to my pussy, skip over it, but you can drag your chin or your nose through my pubes as you make your way down my other leg, then back up. Mmm, yeah.

"Okay, this time, I want you to lick it. Really soft at first. If you've done it like this, she should be really wet already. Now, take your hand and gently pull her lips apart. Just put your middle finger on one side and your index finger on the other, and press in a little, then spread them, and you should see the inner lips. Lick along my inner lips. Not so hard, at least, not at first. That's better. You see my clit at the top? That's the most important, but don't miss the other spots. Just below that is my pee hole. Try gently swirling your tongue around it. That's perfect. Keep doing that for a little bit. After that, I want you to fuck me with your tongue. Oh, yeah, stick that fucking tongue in my pussy. In and out, just like you were fucking me with your cock. Fuck, that's good, Jim.

"Now, go back up and use your tongue to circle and to flick across my clit. Take your middle finger and slide it into me. Do you feel that part of my vagina that's got a different texture? Curl your finger up into that spot, release it, and repeat. Keep working on my clit while you do that with your finger. If you keep an even pressure, I'll cum pretty quickly."

I did my best to follow her instructions. I worked on what I now know to be her G-spot, while I swirled my tongue around her clit. She was really wet, and while her pussy tasted unlike anything I'd ever experienced, I found it intoxicating, and I eagerly drank it in. Sure enough, in just a few minutes, her hips were shaking, and she grabbed my head and pulled it tight into her sopping pussy. I could feel her muscles contracting on my finger as she came. I started sucking on her inner lips, licking some of her juices off of them.

After a minute, to let us both recover - her from her orgasm, and me from the ache I felt in my jaw - she asked if I would do something for her. At this point, I was game for anything. Without ever releasing her grip on my middle finger, she got on her knees with her head on the pillow. She reached over to her nightstand and pulled out a small vibrator.

"I want you to keep fingerfucking me, while I use this vibrator on my clit. While I do that, I want you to start licking the top of your finger. Does my pussy taste good on your hand? Yeah? Drag your tongue up a little ways off your finger. Mmm, yeah, that's good. Go up a little more. Yeah, I know you're right by my asshole. I want you to lick it. I showered right before you got here, so you have no worries. Besides, I came so much my pussy juices ran all the way down my ass onto the bed. Just go slow and circle it with your tongue. Oh fuck, yeah. Keep doing that, but every few strokes, flatten out your tongue and drag it right across my asshole. Oh, fuck, that feels good!"

I had to admit that I wasn't grossed out at all. She was clean, and the forbidden thrill of doing it made it even more exciting. She was obviously enjoying it, and when she started masturbating with the vibrator, I could feel it on my finger and even on my tongue. I added a second finger, which got a moan of approval. I kept circling her back door with my tongue, then running my flattened tongue directly across it. She was getting more and more into it, and her moans were getting louder. Eventually, I put the tip of my tongue directly on her asshole and pushed forward ever so slightly. Susan responded, so I pressed slightly harder, and I could feel her asshole begin to open. I wasn't really interested in my tongue plunging into her ass, but what was happening was so fucking hot I wanted it to continue, so I backed off just a bit, then pressed forward again. This very shallow tongue-fucking she was getting did the trick, and she started to cum.

I kept pressing in and out of her ass with my tongue, while I worked on her cunt with my fingers. Her vibrator was still going full speed, and it all combined to give her a monster orgasm. She had her face buried in a pillow to muffle the moans that had turned into screams.

After an enviously long orgasm (why don't mine ever last that long???), it started to wind down. Just as I was about to withdraw both my fingers and my tongue, she came again. This one didn't last as long, but seemed to be at least as intense. I could feel her vaginal muscles squeezing my fingers, and her ass tightened even further, as I continued to work it with my tongue.

Once that second wave wound down, she withdrew the vibrator, which I took as a sign that she was ready for a rest. I slipped my tongue out of her ass, and as I slid my fingers out of her pussy, I was astonished at how wet my hand and my arm were. They were soaked with that wonderful combination of slipperiness and stickiness, that a woman's wetness provides. I licked the palm of my hand to get some of the taste of her in my mouth, then offered her the two fingers that had been working on her G-spot. She hungrily pulled them into her mouth, savoring the taste of her own massive orgasms.

After just a minute to catch her breath, she shoved my hips and said, "Now, you. Assume the position. Get on your knees and put your face on that pillow."

I did as I was told, and it was only as I was getting up, that I noticed that not only was my cock completely hard, but that there was a puddle of pre-cum on my thigh where my cock had been. Susan noticed and scooped it up with her fingers and smeared it on the head of my cock.

Even as I was getting into 'the position', I was feeling uneasy. First of all, I was way outside my comfort zone, and more than that, it just didn't seem like the most attractive pose for a man. A woman with her ass in the air looks sexy as hell, but with a guy, you get a hairy ass and the underside of his balls as your view - not nature's best, in my opinion. All the same, I did it. She didn't seem to mind the view, and actually seemed to enjoy it, or so she said.

Susan knelt behind me and licked from my left thigh up to my taint, then back down my right thigh, stopping to lap at the drying pool of pre-cum on my right inner thigh. Once she'd gotten all she could, she moved back up enough to lick my balls. She started on the right one, running her tongue lightly up and down on it, then slowly dragged her tongue across to my left one, repeating the process there. On her fourth upstroke, she moved further up, gliding her tongue up to my taint, then continued up and ran it across my asshole. I thought about how good her finger had felt during our second massage session, but this took that to a whole new level.

Susan clearly knew what she was doing and wasn't shy about doing it. Her tongue ran over and around my asshole, using enough pressure that her tongue started to penetrate me. The sensation of having my ass rimmed and licked was incredible, but when combined with being tongue-fucked, it was almost overwhelming.

I have no idea how long this went on, although as intense as the sensation was, it probably wasn't very long, Susan made a ring with her thumb and index finger of both hands and began stroking my cock with them. It was like my cock was being milked on top of the work of her tongue. I could tell I wasn't going to last much longer. "Stop, or I'm going to cum all over your sheets," I muttered between moans.

Not only did she not stop, she sped up her strokes on my cock, and worked her tongue even farther into my ass. I knew I was about to cum, and cum hard, so I followed Susan's lead and buried my face in the pillow to muffle the primal sounds I was making.

When I came, I came so hard I nearly passed out. Susan kept stroking me, as wave after wave of my orgasm hit me. She continued working my ass with her tongue as I came, finally withdrawing her face, then her hands, and easing herself down on the bed next to me.

Thinking I was going to press my cum further into her sheets, I stood up; my legs were wobbly, but I managed. When I looked down, I was surprised to see that Susan had put a towel down under me. It was covered in my cum, but the sheets were fine. I wadded up the towel and tossed it on the floor, taking its place on the bed next to Susan. Her bedroom smelled of sex and sweat, and she looked so fucking good lying next to me, unapologetically naked, her body covered in a thin sheen of perspiration. I smiled at her, and she smiled back.