
My live-in girlfriend of three years, Cindy, has never been quite as sexually adventurous as I’d like, although we do have a good sex life. We fuck perhaps three times a week and we both end up with good orgasms, although I usually cum too soon, so I have to use my fingers and tongue to bring her to orgasm. I don’t mind that, but I have cravings for things she won’t do. Basically, she likes missionary position, and that’s it.
So being the loving person she is, she arranged something for my birthday, that scared but also delighted me.
I have no idea how she found out that there’s this woman in our city who gives ‘happy ending’ massages. But, they’re not your typical happy ending massage, as if I even know what that is. All I know is that Cindy said this woman would be super-intense and I’d love it. I tried to get more information from Cindy, but she evidently didn’t want to spoil my birthday surprise.
As the day approached, I kept wondering about my 6pm appointment. Not only did the notion make me horny, but I was somewhat scared also. What, exactly, did ‘super-intense’ mean? How much did Cindy know about this woman’s service? Did they talk about me? How embarrassing!
My phone’s GPS brought me to the woman’s townhouse quickly and easily, but my heart rate was really fast. I was more excited and scared at the same time than ever. I hadn’t felt like that since the day I lost my virginity with Cindy. In fact, this was somehow scarier.
I rang the doorbell, then said “Hello” with a shaky, high voice. I cleared my throat and said “Hello” better. The lady, Julie, was a few years older than me, but what a knock-out! I was surprised Cindy would let me spend time alone with such a female person. The only thing not particularly feminine about her was her fingernails. You might expect a gorgeous woman to have long nails, but hers were not. Later, I found out why.
She beckoned me in, as my knees felt so weak I could hardly walk properly. She offered me a glass of lemonade while we sat and talked on her sofa for a few minutes. Then, she directed me into a back bedroom and told me to take off all my clothes. No fanfare, no flirting, just “Take off your clothes, I’ll be there in a minute.” Weird, eh?
The room was like entering another world. It was dark, candle-lit, had tapestries on the walls, and a faint, attractive incense, that reminded me of raspberries. I noticed there was faint instrumental music as well. There was a fancy, sheet-covered massage table in the middle of the small room.
I felt several things at once as I kind of reluctantly undressed. Like, “What have I gotten into?” mixed with “Should I actually be undressing in this strange woman’s house?” and “I wonder if there is any danger here?” I briefly thought perhaps a big man with a weapon would appear, take all my money and murder me. A moment later I knew that was ridiculous. But my final though before Julie entered was “I wonder if I’ll even like whatever is going to happen?” And of course, “WHAT IS GOING TO HAPPEN?”
Julie quietly entered the room fully clothed. Was I expecting something else? I think I was somehow expecting her to be nude. Being nude in her clothed presence made me feel ridiculous.
She had me hop up on her table. You can bet my cock was soft as a noodle. So far, there was nothing sexual about this, except she was an attractive woman, and I was nude. But sexual? No.
“Cindy tells me you’d like something more,” she quietly said.
It took me a moment to figure out how to answer that. Finally, I figured the truth was the best response, as it is for almost everything in life. “Yeah, we have a nice sex life, but she won’t do some of the things I want.”
“What do you want?”
“I don’t know. Maybe some… well, something kind of rougher. Something more manual. Like Cindy will sometimes try to jerk me off after I have already cum in her. It makes me squirm, but I rather like that. Just once, I mean only one time in our three years, she massaged my balls. I loved that, but now she won’t do it any more. Even then, If maybe she had massaged my balls a little more thoroughly, I mean, maybe with a little more pressure, that would have been nice.”
“OK, I understand,” she responded as she was already getting down to doing something to me. It was not what I was expecting. She had some soft ropes of some sort and she went around tying my wrists and ankles to every corner of the table.
I just let her do it, but have to tell you, my heart was beating 100 miles an hour.
Once she got me tied down, She leaned over the table, and to my utter surprise, she just ever-so-lightly touched a fingertip along the hair above midline of my ball sack. That was so unexpected! It felt like an electric shock. She did it again, and then again, with a couple seconds between each stroke. I had never felt anything like that in my life. It was at once a great tickle, and very, very erotic.
I was thinking, “I’ve got to get Cindy to try this on me. I think she’ll at least do this. Maybe she’d like me to do something similar to her inner labia.” Suddenly, I noticed my cock was rock hard. When did that happen? It must have been just now as Julie had continued to run her finger along my scrotum several more times.
More internal thoughts. I guess I’m just one of those guys who thinks about everything. Maybe worries about everything. Perhaps I should learn to just enjoy the moment. I digress. I was now thinking that it was super-embarrassing to be erect in this woman’s presence. And naked. Here I was, tied to a strange woman’s massage table, fully naked, and now erect. Oh my!
A new sensation popped me out of my thoughts. Julie was now lightly running a finger along the underside of my cock. She wasn’t holding it with the other hand. It was standing straight up. My cock has to be especially hard to do that. Normally, it lays against my stomach.
This was more electric shocks, but to the max! It was intense. I was kind of craving that she might wrap her hand around my erection and start wanking me properly. But no, for the longest time, she was just doing that super-light tickling thing to the underside of my cock. I felt like I could cum just from that. In fact, that ‘gonna cum’ feeling was starting to build up.
Julie must have been an expert because just before it was too late, she stopped doing that. I just then realized there was a mirror on the ceiling, so if I choose to look, I could watch exactly what she was doing.
What she was doing now was lightly massaging my balls – the very thing I wish Cindy would have done more than just that one time. OK, this was good!
For the first time in several minutes, Julie spoke, “I’m going to slowly increase the pressure. Let me know when it is too much. However, you should know that the moment you say ‘Stop’ I will stop, but I won’t start again. So, be sure you mean it.”
“OK.”
Watching in the mirror, I could see that she now held one ball in each hand, with two fingers below each testicle, and her thumbs on top. Just as she said, she did slowly start increasing the pressure. At first, it was lovely, but after a short while, I wasn’t so sure. The balls were starting to slightly ache, and feel like they were on fire at the same time.
She continued to squeeze harder, then added a sort of sideways back and forth motion with her thumbs. OK, it was hurting, and I wasn’t so sure I was liking it any more. But, I remember that if I said ‘stop’ that would be the end of it, and I might never in my life get this treatment again. I gritted my teeth and just took it with the occasional grunt as she bore down even more. I was determined to take all I could get.
However, while this was happening, something else started happening too. I was building up to an orgasm. I had to say “Stop” because I was about to cum. She stopped.
Julie backed away for a while, then she kind of scooted my legs up. The next thing I know, she was gently running a fingertip around my anus in little circles. And then she backed away again. In the mirror I could see her apply some cream to her index finger. I knew what was coming, even though no one had ever done that. I was sure I wouldn’t like it, but figured I could grin and bear it. Plus, I was tied down. What could I do?
As expected, she pushed that finger into my anus. I was expecting it to hurt, but she did it so slowly, all it felt was wonderful! I was not expecting that. I didn’t know what she did next but the feeling was the sweetest ‘gotta pee’ feeling I’ve ever had. Later I found out she had curled her finger upward and was massaging my prostate from the inside.
She grabbed my penis with her other hand, wrapping her fist around it, and just held it while she continued massaging my prostate.
Oh, oh, the ‘gonna cum’ feeling was building rapidly.
I needn’t have worried, just before it was too late, she slowly, ever so slowly, started pulling her finger out. I could swear her index finger was a foot long.
Now, I really, really wanted to cum, but it wasn’t happening.
She stepped into another room for a minute. I believe to wash her hands. When she returned, she just reached right over and grabbed my super-erect penis, wrapping her fingers fully around the shaft. OK, I was going to get jerked off. Good, that’s exactly what I wanted at that point.
But no, what happened next was the craziest thing yet. She put some sort of oil on the palm of her other hand. You might know what was coming, but I did not. She then placed that greasy palm on the tip of my penis. OK, interesting. Then she started slowly pressing down slightly, and rubbing back and forth. I practically jumped out of my skin. If you’ve never had your glans rubbed like that, you’ve got to experience it. If I hadn’t been tied down, I would most certainly have jumped off the table. I said “Stop” but she just laughed and kept going. It was terrible. It was excruciating. The worst tickle of my life. I couldn’t stand it, and yet, I wanted to see just how much of this torment I could take. But it was so intense!
I was just about to yell “Stop” between all my squirming, moaning and laughter, but I noticed it wasn’t feeling so bad any more. Now, I was feeling something like a combination of ‘gotta pee’ and ‘gonna cum’ feeling.
The next thing I know, pee was squirting out of me in little spurts. There was nothing I could do about it. You’d think Julie might stop at that point, but no, she just kept right on going.
And then, fully out of my control, I felt orgasmic spasms starting. I was going to have my orgasm. Things would be over in a moment. At that point, Julie stopped, grabbed the tip of my cock between a thumb and finger, and squeezed it closed. “My god this can’t be good!” I thought.
She just continued to hold it that way for a few seconds, and then my orgasm started in earnest. I was cumming. But I wasn’t cumming. She had trapped the cum inside. Oh, it was excruciating. Or was it? There was no pain, although there was a ton of fear. Would something inside me break? I felt the internal pressure of my continuing orgasmic contractions trying uselessly to squirt the cum out, but it wasn’t happening. My body kept trying. I swear, the contractions lasted twice as long as usual.
At least a full minute after the contractions subsided, Julie finally let go, and a single long spurt of cum rolled out of me.
We were done.
Here’s the thing: We weren’t done. After letting the cum out, Julie let go for perhaps 30 seconds, but then she grabbed my cock and started that horrible palm rubbing thing again. I couldn’t stand it. I said “Stop” right away. She just laughed, and kept torturing me for probably two minutes, which seemed like ten minutes, until my erection subsided into just a little noodle.
This time it really was over. Julie left the room, saying over her shoulder “Take your time, I don’t have any more appointments this evening.”
I laid on her table a good five minutes, then tried to get up. I said ‘tried’ because I had to make two attempts. I was just too weak and shaky.
When I finally dressed, I met up with Julie in her living room, told her how much I loved the appointment, even though I wasn’t so sure. I think I liked it, but did I? It had been the craziest situation I had ever been in. In fact, I was pretty sure I’d never put myself through anything like that again. As I drove home, I felt so remarkably sexually satisfied. Even my balls felt well worked. They were kind of heavy, in a nice way, from being squeezed. Still, I was convinced that would be a one-off. I’d never do anything like that again, ever!
At home, I told Cindy all about it, almost a blow-by-blow description and during the discussion, I became incredibly horny, as did Cindy. We ended up fucking like rabbits. I came in her hard, as if I hadn’t already cum that day.
Literally, less than one day later, I was already trying to figure out how I could book another session without upsetting Cindy. I mean, as a birthday gift, great, but wouldn’t Cindy be jealous or upset or something if I wanted to go back to Julie?
For the next several days, I was trying to work out how I could make another appointment happen, when suddenly, at dinner, Cindy announced, “You know, Julie does women, too.”
This really surprised me because I had always thought of Cindy as somewhat sexually reserved, prudish even.
Oh, my god! Of course I immediately said, “Oh I know you’d love to have a session with Julie.” Then, thinking quickly, I added, “Gosh, I’d do it again if I could.”
Cindy, understanding sweetheart that she is, immediately said that it would be fine with her. That I could book as many sessions as I’d like.
So, Cindy did have her session, and as I suspected, just like me, she wasn’t sure at first but a day later couldn’t wait to book another session.
I had another session with Julie which was even more delightful than the first. Cindy had another session and came home saying, “Julie mentioned that she also does couples’ sessions.” I have no idea what that might involve, but can’t wait to find out.