Massage Chronicles - Trina Watches

Trina was the second regular massage therapist I had seen. She came via a family recommendation as her co-therapist Riley was a friend of my wife's girlfriend. Still pretending I was an improving athlete and getting older meant that over the years massage treatments became more frequent and necessary. I liked them much better than going to the chiropractor. There was something about surrendering your muscles and body to someone who knew what they were doing.

Even though she was younger than me, she was kind of attractive in a Milfy sort of way, I would have guessed that Trina was part Filipino, but later found out she was Fijian. She had shoulder-length dark hair, was shorter in stature with a light chocolate brown complexion, and always seemed to have fairly heavily contrasting makeup. Not my style but I never made any comments about it.

Trina was always friendly but not too chatty, which I liked, and her massages were effective for all my sport-related muscle ailments. Never really inquiring, I chose not to get to know her in much more of a personal way.

Trina's massage was very relaxing and even intimate, despite not being sexual in any way. The touch always felt great. Something about the dimmed lights and spa music as well, I guess. Coaxing knotted muscles into relaxing without having me jump off the table was one of her forte's.

I am going to guess it was about the tenth or eleventh appointment when I noticed things changed a bit. For the better as far as I was concerned. I really started to enjoy her upper leg massages and a few times she even did a stomach massage. Trina explained that the stomach massage had to be done counter-clockwise as that was the way the digestive system circulated.

"I'm sorry I've got your shorts all oily." She apologized at the time.

I know lots of less timid people took off all of their clothing during a massage, but even with the draping, I had always kept my briefs on for massage up until that point. The oily briefs remark resonated with me. Something in her voice that time said to me that I shouldn't be so conservative and forget about wearing underwear.

Three to four weeks later I made another appointment. Trina met me in the room for the preamble checking me over before the actual massage treatment. Once she looked over how I was standing, my shoulders, hips, and my posture, she got ready to leave the room, so I could disrobe.

"Okay I'll let you get ready, I hope I didn't get too my oil on your shorts the last time."

"No, it was okay I just soaked them in the sink before dropping them in the wash." Politely I lied not wanting her to feel guilty "I guess I could just leave them off next time." I didn't really want to volunteer my eagerness for going commando under the draping.

"It's much easier for me, but it's up to you, whatever you are comfortable with." Trina raised her heavily dark-penciled eyebrows, very much opening the door.

What the fuck. I tossed my briefs into my rolled-up jeans and went under the draping. Trina always used a really thin draping fabric, assuredly she'd be able to see I was nude.

That session completely turned the corner in shifting the massages from being therapeutic and intimate to therapeutic and sensual. With no briefs on Trina's hands freely roamed over my bare glutes and really high on my inner thighs. She definitely grazed my sac a couple of times even.

I gasped the second time it happened.

"Is everything okay?" She asked while shaking my leg by the ankle.

"Yeah." I wanted more without saying you can touch me more if you like, "it's good." Whether she was testing the waters or not, I wanted more.

Although I wasn't erect, my cock was plenty excited by the time I rolled over on my back. Trina did the customary massage over the draping for the full body check. This time astoundingly it included a pretty good grope of my shaft through the draping.

'Oh, fuck do that again!' I thought to myself.

Her eyes had a look of pause. I guess she was ascertaining whether or not I would object. I didn't say anything but stupidly smiled up at her approving while my cock solidified.

"Do you want something over your eyes?" Any tension that was in her expression before, vanished.

"Yeah, why not." My cock twitched involuntarily.

Trina placed a small folded towel over my eyes and started what was my most sensual massage to date. She pushed the draping away from my legs one at a time, tucking the fabric between my legs. She was really pushing high up on my thighs and grazing my balls a lot. I think not being able to see her made it that much more imaginative and sensual. I relaxed my legs letting them fall apart, and by the time she was working on my other thigh, her fingers were going between my balls and legs regularly. Whatever draping was there ultimately became untucked. I loved it.

Making a point of having a smile on my face, I wanted to ensure that Trina knew I was both approving and enjoying. My thick springy erection was pushing the sheet up and must have looked huge under the thin draping. She finished with my legs, massaged my arms then shoulders. After massaging my shoulders, she pushed the draping down my chest. Did my pecs, then pushed the draping down to my waist for the famous Trina stomach massage.

Without any underwear on there was no natural border to stop the draping at either. My cock felt sensitive and needy.

The fabric arranged on my hips was bunched up kind of pushing my still hard cock to the side and within a few circular massages it felt like Trina's hands were massaging over my pubic hair with each counter-clockwise movement. I took quite a deep breath each time her palm pushed across my pubic hair. My heated throbbing cock fought to get free from being caught up in the draping.

"Okay I'll see you outside" Trina pulled the draping up and the massage finished much too soon for my liking.

After she closed the door behind her, I sat up on the massage table before getting dressed trying to digest everything that just happened.

It took me quite a while to get dressed.

"How was everything?" Trina asked processing my payment at the front counter.

"It was really nice, thank you." I didn't really know what else to say. (thanks for making my cock really hard!)

I found myself looking down her top, while she printed off the receipt.

"Do you want to make another appointment?"

"Yeah, I should"

"Okay, I have something next week. It's later Thursday."

"Sure." You can massage around my cock some more.

As soon as I got home, I lubed up and jacked off furiously.

Thursday couldn't come soon enough.

When I arrived, the vibe seemed strangely professional. I was resigned to the fact that she'd possibly regretted the erotic parts of her massage and was going to revert to a completely therapeutic treatment. I sighed quietly. That it was a one-time only erogenous episode.

Still hopeful, I took off my briefs the same as the previous appointment.

Trina's hands immediately wandered sensually and I relaxed reassured the massage was going to mirror the previous one. While I was on my stomach the butt massage was heavenly, and even more, frequent luxurious brushing of my testicles had me rocking my hips side to side.

I got the distinct impression that while Trina was holding up the draping that she was peeking at my erection as I flipped onto my back.

"Do you want me to cover your eyes?" She asked smiling tellingly.

"No, it's okay." I thought I'd watch this time, to see if I could read anything from Trina's expression while she massaged me. This did kind of seem a little risky since my wife was friends with her associate. I thought it unlikely that they would talk, still...

There was no tight folding and tucking of the draping. When Trina massaged my thighs this time, she enticed an absolutely massive erection by smoothing up my legs, coming incredibly close to my cock and balls, but frustratingly not touching. She did an excellent job of teasing and making me want more.

The same thing happened by the time she wrapped things up with her stomach massage. It was slower. Even more sensual. Still massaging her hands over my pubic hair and having my raging cock conveniently trapped up in the draping and pushed to the left side. So very tormenting.

"Okay, see you in the front," she smiled strangely then walked out of the room. I sat up on the edge of the table nude again. Subconsciously the need to release all that pent-up sexual energy was driving me crazy. It was like an out of body experience, and I reached down slowly stroking my still thick cock. The residual oil on my hands lubricated it enough to quickly erect my quivering penis.

I suppose if I was smarter, I would have not been sitting facing the door, stroking my cock, but I was. It was almost impossible to not want to stroke my heavily engorged shaft. I squeezed gliding my fist down like a big elephant's trunk. Stroke by stroke my penis stiffened and straightened pointing out then up. Just as thoughts of how crazy this was and that I should get dressed and go home to masturbate, Trina walked in and caught me red-handed. Or I should say cock in hand.

I froze. (shit)

Trina quickly closed the door behind her. "Sorry I just wanted to see if you are okay?"

"Sorry."

"No, it's completely natural." Her voice was semi consoling yet curiously arousing.

"Could I watch?" Surprisingly she asked, "if you want to... you know... keep going?"

I was in shock, apprehensive, but part of me really thrilled. My cock stiffened so much in my hand like it was telling me to jerk it off. 'This is crazy!'

It wasn't well lubricated but I had enough teasing from the earlier massage that the urge to jack off took over any thoughts of embarrassment.

I didn't really look at Trina much, and only a handful of slow strokes to the ridge in my cock had me so damn close to the edge.

I reached down and cupped my balls with my left hand and erupted all over my stomach, cascading cum on my pelvis cock, and balls.

"Wow, there was a lot!" Trina commented favourably. Her eyes open wide contrasting with her darker skin tone seemly mesmerized by the amount of my jizz. (I was a big cummer.) A moment later handed me a small towel to wipe up with.

I did not take too long to get dressed and paid my way out with very little conversation. I just sat in the car before driving home. In my mind, I wrestled with what I just did. You are so fucking stupid! I was sincerely worried about the repercussions.

It took me three weeks to get the nerve to book another appointment.

Credit to Trina, everything was super chill and normal when I came back a month later. If anything, it was even a little friendlier. All of that helped put me at ease. Any pent-up anxiety kind of melted away. I even got the sense that if it weren't for the receptionist, Trina would have stayed in the room and watch me undress.

The massage started very normally with her excellent back work and the leg massage that I so eagerly anticipated. Trina did not disappoint. Sliding her hands along my inner thighs there was much more accidental balls touching and grazing. I pushed my ankles apart so she had more room.

Flipping onto my back, Trina started with my upper body this time, departing from her normal routine and beginning my stomach and lower abs massage much earlier.

She slowed her hand swirling movement inching until it was almost a snail's pace, rubbing her palms back and forth over my pubic hair, then asked kind of boldly, "Do you want to show me again?"

"Sure." My cock hardened nicely before I even touched it. I knew what she meant. She could see how hard I was and wanted to see me jack off again. The exhibitionist side of me wanted to put on a show, and my cock was needy enough that any thoughts of being inappropriate were buried deep in my subconscious.

With two hands, Trina slid the draping off me. "Do you want some oil?"

"Sure" I nodded as she drizzled some oil on my open hand. "That's good." I indicated for her to stop.

I started stoking my cock and she massaged up and down my legs and thighs. I guess my breathing gave things away as I rapidly closed in on my climax. As I did, her hands moved up my inner thigh between my balls and legs. My breathing got super quick and Trina started rocking her palm and finger and thumb between my balls and leg. Pressing very firmly rubbing my taint and the side of my balls where they met my leg.

"Fuck" I muffled my cursing under my breath to ensure that anyone outside the massage room didn't hear and jetted cum all over myself, everywhere. It shot on my face, my neck, my chest, shoulders. I was creamed. Trina kept up her massage until I finally stopped.

"Wow, there was so much, again." She commented smiling while grabbing some tissues and dabbing me down. She wiped up all of my cum. "Do you like that?"

I assumed that she was talking about what she was doing to my balls. "Yeah, I love having my balls played with."

"Really? Is that what made so much?" She asked as if she honestly did not know. Perversely she seemed really happy with the magnitude of my ejaculation.

"Sometimes. Usually. It makes me cum hard and a lot." I admitted but left the reply leading.

She finished wiping the cum off of me and was giving me a nice light full-body caressing massage while asking me for more details. "I don't think all guys like that?"

"Ha yeah, I guess I have strong balls. The more the better."

"I like seeing it come out." She admitted again smiling kindly.

We finished up pretty normally. I wondered looking at the few people waiting in the reception if that had any clue what had just gone on behind closed doors.

This style of massage session became the norm for the next five or six times. There seemed to be some unwritten rule for Trina, that she could not put her hands on my penis. Balls were okay, but not my cock.

Every massage ended the same way with me on my back on the massage table, jerking off while Trina tried a few different things on my balls. I get the sense she was experimenting for the largest load or biggest cumshot, since she always commented on how she liked to watch it come out.

The next session that followed, consisted of her holding one of my testicles in each of her hands. She massaged them and kneaded them between her fingers. Her fingertips massaged the shape of my testes inside my nutsack while I erupted all over the place again. It was very intense.

A couple of sessions later this changed to her jamming her clenched fist under my balls and massaging deeply. At times it felt like she was trying to push the underside of my balls up really hard. That was another good one with a suitably voluminous eruption.

I remember watching Trina at least once while I was cumming. Her eyes were focused on my jetting cock.

At the end of that session, she told me she was moving out of town. I was not happy to hear that Trina was moving back east to be with her family. I tried to book as many appointments as I could get before she left, conscious that I did not want to be raising my wife's eyebrows.

The weather was also getting a little colder in the fall-winter, so each of the last two times that I saw her for massage, I suppose I was not hanging as low.

Maybe my balls were too tight for the previous style of massage, so she was kind of kneading them while I was stroking my cock by placing her flat palm on my balls and rubbing it around in circles. I don't know what changed at that moment but for some reason, she kind of spanked her open palm against my tight nuts.

"Oh yes!" I really liked that sensation, and in the heat of the moment did not have any qualms about letting her know. I let my knees fall apart.

She did it again, and then a couple more times spanking my tight balls with her palm.

"Fuck yes!" I was much more encouraging this time. It was so intensely pleasurable to me.

She spanked a little harder and faster, while my hand moved in rapid quick strokes. I cursed under my breath and an incredibly intense climax moved through me. I opened my legs wide to make my balls an easy target, but probably she only got a couple more spanks on them before I unleashed cum.

The first shot went over my head, with wads of cum landing on my face and upper body.

Trina slowed then lightened her spanking of my testicles to a slow palm massage again "Wow that was a lot!" Her smirk was rudely proud.

"That was crazy good!" I complimented her. That was the first time I had someone else slap my balls when I jerked off. I had done it a few times myself, but having someone else do it was wonderous.

The clean-up took quite a while.

I gave her a one-arm hug before she left the room. Inside, I wished that she did not have to move, so my last massage with Trina would be about a month later.

She seemed to be pretty well prepared by the time I was on my back jacking off my cock. I took my time with really slow strokes wanting to make it last. Trina kneaded my balls the same as before.

I was hoping that she would try her balls slapping on my nuts again. She did. This time differently. The first couple of slaps were as light and fast as before, then it felt like she cupped her hand or something and spanked my balls much more firmly.

"OH fuck!" My body shuddered.

"Was that okay?" She asked sincerely. I suppose worried that maybe she'd hurt me

"Yes!" Instead of tightening, my balls kind of loosened making themselves a better target.

"Want me to do it again?" She smiled in her discovery.

"Please yes!" I splayed my knees feeling my testicles fall down between my legs as they loosened.

She repeated with the next firm spank on my balls and my cock got so fucking hard, even though I was barely touching it.

Trina spanked my balls faster and firmly. It felt like I was going to cum just from the slapping of my testicles.

I couldn't resist at all anymore and jerked my cock quickly as she continued slapping my balls deliciously.

"Yes, fuck yes!" I was ready to cum, and so hard.

My chest and stomach were heaving, and Trina kept it up as I started ejaculating. One of her spanks on my balls was exactly as my second jet of cum shot out. It was so intense I swear I almost passed out. She put two and two together noticed the timing of my cum shot and gave me a couple more really firm slaps on the balls until my spurting cream slowed to an oozing flow.

I struggled for a minute breathing as if I just completed the 100-meter dash. It was the most intense assisted jacking off session I'd ever had to date.

"That was a lot!" Trina had that perverted smile again and seemed proud.

"It was a lot, fuck!" My whole body felt coated in sperm. The intenseness of the orgasm made me less aware of where my spunk landed, but it felt like it was everywhere. "it was so intense."

"I can see that!" Her palm was still gently doing a circular healing massage on my spent balls.

This time she had some moist wipes which made clean-up a little easier.

I looked at Trina in the eyes, after I paid the fee at the reception desk. I definitely felt something much more in her return gaze.

Sadly after that massage, it would be the very last time I saw Trina. She moved back east.