The time I [M] got a sensual massage and jerked off for my masseuse

I love getting massages. I started getting them a few years ago to relieve some pain I had from working out. Massages were never sexual for me at first. They were a way to relax and ease my mind and body. A good massage can always put you in the right mood. But I’d be lying if I said I was never turned on by these massages. Occasionally I would get hard during a massage and hope that something would happen, but sadly nothing ever did. I remember one of my first massage therapists [MT] finished my massage while I was facing up on the table. I was covered, but she pulled my covers over me really tight so that the outline of my cock was visible. She kept pulling the covers down tighter over me even though it was unnecessary. It felt like she was just trying to see a better outline of my cock. I was already hard but the thought of this woman trying to get a better look at my cock was a huge turn on for me. I never made a move though since I wanted to keep things professional. My hard cock remained under the covers undisturbed.

Time passed and I moved on to different MTs. I like to try out different MTs since every woman has her own style and skill set. No two massages are really alike. I’ve gone to a few different MTs over the years, but more recently, I came across a woman on craigslist advertising her massage business. Normally craigslist is sketchy, but she looked legit. She had pictures of her equipment, so I could see that she had a real massage table. She also had a bunch of massage devices that looked like medieval torture tools. It looked like she knew her stuff, so I messaged her and set up an appointment.

After some identity verification, I showed up to her house for my appointment. She operates her business out of an extra room in her house. She greets me and we exchange pleasantries and she asks me what I want out of the massage. I tell her normal non-creepy things and she seems satisfied. She has to deal with a lot of weirdos on craigslist so I think she’s just glad I’m not one of them. She leaves the room and I remove all my clothes and get on the table face down. She only left a medium sized towel for me, so I use it to cover my ass. Secretly I’m thankful it’s a smaller towel. Normally MTs give you full sized sheets to completely wrap and cover you, like you’re preparing for an artic expedition. Heaven forbid, they see your ankles. So I was glad that I could show a little more skin. You honestly feel freer when there’s less covering you. If it was totally up to me I would probably just be naked.

My MT returned, let’s call her Clara. Clara is probably twice my age at about 50. She’s a Latina woman with long black hair that, if let down, would just touch her giant boobs. She’s on the thicker side and due to her age I wouldn’t normally be attracted to her, but I’m not looking for a date, I’m looking for a good massage. So Clara begins with my back and shoulders.

Clara and I talk throughout the massage. She’s a cool, smart woman and we hit it off. The massage progresses and close to the end of the one and a half hours, the most amazing thing happened… nothing. Absolutely nothing happened. It was a normal massage just like I wanted and I paid then left. But in the back of my mind I definitely thought she might be up for more. She seemed like the type.

A few weeks later, I scheduled my second massage. The first was a great massage after all. I showed up on time and the massage proceeded as normal. I was enjoying myself, feeling as free and relaxed as ever. The little towel blocking my crotch was the only thing preventing me from absolute freedom. But I didn’t mind keeping it there.

Half way through the massage, Clara asks me if I want to do the assisted stretching again. We did some stretches on my first massage, so I happily agree to do them again. I actually enjoyed the stretches and it’s something that my other MTs didn’t do. So while I’m facing up she moves towards my legs and asks me to assume the stretch position.

She takes a hold of my leg and begins to bend it the way she wants. Picture a butterfly stretch with just one leg. As she’s facing away from me and the table, she begins to stretch my legs open. My hips widen and I really start to feel the stretch. The stretch is amazing, but my towel doesn’t seem to enjoy it. The towel can’t hold on and soon my dick flops out. I’m now completely exposed.

At first Clara doesn’t see it. She’s facing away from me during the stretch. For a moment I consider whether I should put the cover back on myself. It would be really easy to, but I decide against it. Fate has just handed me this happy accident. My dick is now fully exposed and facing my masseuse. Why would I waste this opportunity? So I endure the stretch a little longer while my penis is flopping about. Clara finishes and turns toward me and looks down at my flaccid dick.

“Oh wow. Looks like you lost your towel.”

“Oh yeah. It slipped during the stretch.”

“Don’t worry. I’ll fix that for you.”

She smiles and readjusts the towel so that it’s back over my dick. She didn’t seem upset by the accident. If anything she seems happily surprised. The massage continues but now I feel a bit bolder and a bit friskier. The extra exposure is definitely having an effect on me.

Our conversation continues and it somehow steers toward my past MTs. I tell her about the time I went to an Asian massage parlor and got a happy ending. My story is genuinely interesting to her and she probes me more for details. I’m honest with her and I tell her that the whole thing was awkward. I wasn’t expecting a happy ending but it just kind of happened. They lady didn’t seem into it, and I didn’t finish. At a certain point I just asked her to stop and I left. Worst of all the massage was awful. Clara laughed at that.

I then ask her point blank:

“Have you ever given a happy ending?”

“Oh no, I’ve never done that before.”

“Well I learned from that experience that I wouldn’t really want to do it again like that. I would only want to do it if my masseuse was into it. It’s only fun if both people are into it.”

She agreed and we left it at that. I didn’t directly ask her for a special massage, but I think she got my message. Later that night, after my massage, she texted me:

“Ok. I would be willing to give you a special, longer, full body massage for a higher price. At 2 hours, the massage is over, even if you don’t finish. It’s about the massage itself. Not about cumming. How does that sound?”

“That sounds perfect to me. I’d rather have it be about pleasure anyways.”

“Great. I’m really looking forward to this. I’ll also be able to massage parts of your body that I normally don’t get to massage. I’m not talking just about your cock either.”

I immediately scheduled my next appointment.

When I showed up for my long massage session, it was already dark out. Clara greeted me at the door with a smile on her face. She was happy to see me. I was happy to see her. She led me to the massage room and I immediately noticed the difference. The room was darker than before. She also had lit some candles to set the mood. I was already getting excited.

I walked over next to the massage table and stood in front of Clara. I removed my shirt. She didn’t leave the room. Clara continued to watch me. I then took off my shoes and socks. Only my sweatpants remained. I slowly slid my sweatpants down in front of my masseuse. I decided before hand not to wear any underwear. As the elastic band from my sweatpants slid past my hips, my cock popped out.

“I see you’re not wearing any underwear.” She laughed.

“I came prepared.” I smiled back.

I wasn’t hard but my cock was nice and full. It was ready for my massage. I climbed on the table and laid face down, making sure to tuck my dick down so it would have room to grow.

Clara’s new massage started like her other massages. She worked my back and shoulders first. But this time I was completely naked, and I felt totally free. As the massage continued my excitement from my nakedness settled down, I began enjoying the massage for what it was. Her long strokes across my body worked all my knots as I enjoyed the euphoria of the evening.

Her strokes down my back grew longer and longer with each move. Soon she was reaching the top of my ass. Since my ass was completely exposed, she had no barriers preventing her movement. On her next stroke her hands went all the way over and down my ass. She then walked along the side of the table and stopped at my ass. I was already beginning to feel my erection grow.

Clara stopped massaging my back and began solely focusing on my ass. At first she worked the sides of my ass, making sure to press into the cheeks. Apparently there’s some important nerves or something in your ass. I couldn’t tell you. All I can tell you is that her ass massage felt incredible. Clara didn’t stop at the sides though. She worked my whole ass. She squeezed my cheeks together, then pulled them apart. She worked the bottom of my ass as well. My dick, now flat against the table pointing downward, was at full attention. My hard cock was clearly visible in between my legs. As Clara massaged the part of my body where my leg meets my ass, her hand crossed my cock just a little. She repeated her motion on the other leg. My cock felt her warm hand again. I was so turned on. She was teasing me and she could tell I was enjoying it.

Next she did something that was unexpected. She took out some disposable plastic gloves and put them on. Where was this going? Was I about to get my prostate checked? She had told me to shower before I came over, but now she explained that she wanted a little extra protection for herself. She wanted to go further. After putting on the gloves, she added some sort of oil to her hands. From my legs, she slowly worked her way up my body back to my ass. Then she spread my butt cheeks so my asshole was exposed. With the same careful attention she uses in all her craft, she began to massage up and down my crack, passing my asshole each time.

Oh shit. I thought to myself. No one has ever done this to me. I couldn’t complain though. I was actually enjoying myself.

She continued to work my ass crack with the intensity and resolve of an athlete. No place on my body was off limits for this woman. From my asshole, she moved down across my taint and to my balls. She massaged each for a moment, and moved to my now pulsating cock. While I still laid on my stomach, Clara began massaging the shaft of my cock. It felt so good, but my cock was straining under the pressure of the table. It felt like I was ready to fuck a hole through the table.

“Hold on,” I said. “I need to readjust.”

I got up on the table and stood up on my knees. I then lowered my head back down on the table but kept my ass in the air. My cock and balls were now dangling freely in the air.

“That’s better,” Clara said. Immediately she grabbed a hold of my dangling balls.

Clara grabbed my balls tight, and massaged them at the same time. In a certain sense, I was completely at her mercy. She could do anything with me and I’d let her. I was enjoying the massage too much to say no. While still holding my balls in one hand, she wrapped her other hand around my cock. Slowly and sensually, she began stroking my cock.

She moved up and down my shaft in a slow and careful way, like she was milking me for every ounce of pleasure. After stroking me for about a minute, she put all her attention on the head of my penis. She wrapped her fingers around the head and massaged the tip with precision only a masseuse can offer.

Clara continued to work the head of my dick for another minute. Her touch felt so good. I really didn’t want to move. But after a minute she took her hands away and took off her gloves.

“Let’s continue with the massage,” she said. “Go ahead and get back on the table.”

I obeyed her instructions and laid back face down on the table. My dick was rock solid at this point. I wanted her to keep stroking my dick so badly, but I knew we were doing this for the massage. So I knew the massage must continue.

“You do have a really nice ass though,” she let me know.

“Thanks. I’m glad you like it.” I was smiling while my head was in the head rest.

She slapped my ass a little to watch it jiggle. Then she moved down the table.

Within the next 10 minutes or so, Clara finished massaging my legs and my feet. It’s easy to lose track of time while getting massaged, but I knew we were now on the last half of the massage.

“Can you turn over for me? It’s time to massage your front.”

Yes ma’am! I thought to myself. I was more than ready to flip over. With no hesitation, I turned around on the table. Now my hard cock was fully exposed to the open air and my masseuse. My young, muscular body was on full display for this woman in all its glory. The massage had relaxed my cock back down from being diamond hard, but I was still erect and turned on. She put one hand on my abs and one on my thigh as she took in the sight of this young boy on her table, naked in her own home.

“Would you like to do the assisted stretches again? I have some new additions this time.”

“That would be wonderful.”

I put my leg in the same position as before. She took my left leg and stretched it out to the butterfly position. Clara was next to me facing towards the head of the table. She had equal view of me and my leg. As she stretched out my legs and hips, she took her forearm and began sliding across the inside of my thigh. Her arm was now a roller, rolling out any soreness in the interior of my leg.

This is new, I thought to myself. I like it though. She continued rubbing her arm up my leg. Soon she was near my groin. Oh shit. This feels better than I thought it would. Is she going to stop? She didn’t. Her arm kept going. Her forearm continued up my stretched out leg and met my dick laying openly on my stomach. Her arm then rubbed straight across my cock.

“Oh fuck.” I quietly let out. “That feels good.” Her arm went back across my dick the other way. Any softness left in my cock evacuated immediately. Any blood left in my brain evacuated down to my cock.

I was at maximum hardness once again.

Clara slowly repeated the whole motion multiple times. Each time her arm met my cock, I felt a moment of ecstasy.

“Now it’s time for the other leg,” she said.

Clara placed my left leg back on the table. She walked around the table and picked up my other leg into position. After the short butterfly stretch, she started rolling her arm up my leg once again. Each time she rolled over my absolute erection, I knew I was living my dream massage.

After finishing my stretches, Clara continued to massage the rest of my body. She worked my legs, my chest, my abs, then, with our session winding down to an end, she grabbed ahold of my cock.

Clara wrapped her hand around my still erect cock and started to stroke me. Her hand, lubed up with oil, slid effortlessly up and down my shaft. Each time she stopped directly below the head of my dick. With her other hand, Clara put her fingers gently around the head of my penis and began massaging just the tip, maintaining the same rhythm as her other hand.

Finally I had done it. After years of getting massages I was finally getting the happy ending I always wanted. My buck-ass naked body was completely free in this near stranger woman’s house, in this warm room lit only by candle light. As her handjob continued, the pleasure of the moment became all that there was. My mind shrunk to the size of the current room. Nothing else existed outside of the present moment.

A minute passed and her strokes quickened. Another minute passed as she moved to work my balls in unison with my shaft. Then another minute passed, and the pace slowed. Clara began to wind down the handjob. Soon she was gripping my shaft again, holding it tight but not moving it. She placed my dick back down on my body. She then moved to the end of the table near my head. Clara began massaging my head, then she moved between rubbing my chest and my head.

“I hope you enjoyed your massage. It looks like we’re out of time.”

“That was the best massage I ever had.” Even though I didn’t come, I told the truth. We had already agreed beforehand that it wasn’t about me getting an orgasm.

“I’ll leave you for a moment to catch your breath and get dressed.” Clara left the room to wash her hands.

In the silence of this woman’s massage room, I sat up on the table and felt my own nakedness. I felt incredible. My dick was still rock hard and I wanted to cum, but the feeling sitting there naked was enough for me. I felt empowered.

I thought about getting up and getting dressed, but I decided against it. I wanted to enjoy this moment as long as I could. Soon Clara came back in the room.

Without saying a word, Clara walked up to the table next to me. I was now sitting up, with one leg on the table and one leg off. My cock was on full display.

We began talking about the massage and maybe about something else. I honestly don’t remember. My mind was on my cock. I put my hand around my cock and slowly squeezed it. Then I rubbed my tip. Something about my setting was an incredible turn on for me. I was naked in from of this fully clothed woman subtly stroking my cock as she watched me. It felt like I was a Greek statue with a cock as hard as the marble I was made of, and she was an art patron, admiring this little art show I was putting on for her.

“You know I still really want to cum, right? How would you feel if I masturbated now?”

“Fine by me,” she replied.

I didn’t need any more encouragement. I moved to the edge of the table and put my legs off the side. I was now sitting on the edge facing Clara. She moved next to me and moved in close. She placed her hand on the inside of my thigh. I grabbed my cock and started masturbating.

The sexual power I felt wasn’t like anything I felt before. This solitary act of self-gratification had become a peep show and Clara had a front row seat. I’ve never been more aroused. My strokes became more and more aggressive. The build up from the whole night was coming to an end. All the sexual energy I had built up during the massage was now being unleashed on my cock. My dick was so hard it felt like I could easily touch the ceiling. And even if it couldn’t, I knew my cum would make it the rest of the way.

Soon I felt something building deep inside me. An orgasm was brewing from depths I had never reached before. With each successive stroke of my cock, the orgasm reached another level upwards. I could feel it building faster and faster, in an almost exponential way. Clara, while still rubbing the inside of my thigh, put her lips on my shoulder and began making out with my arm getting ready to deliver my orgasm.

My orgasm reached the point of no return as I furiously wacked my cock into oblivion. Suddenly, without any conscious effort, I fell backwards on top of the table, closing my eyes as jizz erupted from my volcanic cock. Maybe I was close to blacking out. I can’t really say. All I can say is that it felt like my mind was falling into a pit of eternal ecstasy and oblivion. It was the best goddamn orgasm I ever had.

I don’t even know how much cum came out of me. It felt like buckets. Clara wiped it off of me with a towel before I even had a chance to recover and sit upright again. I thanked her for the wonderful evening, put on my clothes, gave her a hug, and went on my way.

Source: reddit.com/r/gonewildstories/comments/qinpr3/the_time_i_m_got_a_sensual_massage_and_jerked_off