My [M] long term massage therapist [F] recently went further than expected

I never thought I'd be sharing a story here, but something wild recently happened to me and I wanted to write it down as a sort of anonymous confession. Heads up that this story contains cheating, so if that's not your thing click away now.

I'm going to be intentionally a little vague for obvious reasons, but for some background context I've been seeing the same female massage therapist, we'll call her Emily, for the last five years or so. I'd say I've seen Emily on average once every other month, usually opting for hour and a half appointments. I'm around 30 years old, and I would guess she's in her late 30s.

Emily is a fantastic massage therapist. I started seeing her five years ago after suffering from a sports related overuse injury, but quickly realized how relaxed and less anxious I felt after sessions with her so I continued going regularly.  She gives off a somewhat free-spirited hippy vibe, but is incredibly down to earth and kind, and over the years we've built up a friendly rapport with each other. We don't typically talk all that much during the massages, but will spend five or ten minutes at the beginning and end of each session chatting with each other. Through these conversations I've learned a fair bit about her history, including her husband who she seems to adore. I've also told her plenty of times about my long term relationship with my girlfriend who I live with.

In all the past appointments that I've seen her, there has never been any inkling of sexual activity. I would guess that like most men who get massaged by women, I have had the one off passing sexual thought, but it truthfully hasn't been something I've given much active thought, and isn't something I actively fantasize about or seek out. Before this I also have never cheated in a relationship. I'm not trying to make any excuses here and you can criticize me for being an awful person as much as you want, but I digress.

While the massages have never been remotely sexual, I would say that her massage style is on the slightly more sensual side of things, often slow and soft as compared to deep tissue, but that's one of the reasons I enjoy it so much. It seems corny to say, but her massages feel like both a physical and spiritual reset. She seems to always be able to figure out exactly where my body is holding tension and stress and gently ease it out. In the past we've briefly talked about her sort of "philosophy" of massage, and while I won't go into it all here, I'm fully convinced she's able to work on something deeper than just the physical body through her touch.

I'm probably rambling though, so I'll just jump right into why you're likely reading this. This all happened a few weeks ago, one afternoon when I took off a little early from work like usual and walked the short distance to her massage studio. She works at a sort of wellness co-op place in a large building downtown, which from the outside just looks like any other office building. Once you make your way into their area though, you're transported to an incredibly warm and calming atmosphere.

Like usual Emily welcomed me in and led me into one of the rooms. We chatted and caught up with each other about the last month or so since we had seen each other, and as always she asked me if there were any particular mental or physical areas where I was feeling extra stressed. I'm someone who tends to manifest mental stress and anxiety physically, which Emily is by now well aware of, so it's not out of the norm to talk about those reasons as well.

I've truthfully been having some relationship problems with my girlfriend, mostly stemming from our vastly mismatched sex drives, and had been having tough conversations with her throughout the past week that had been causing some added stress. Without going into the reasons why, I did tell Emily that I was a little extra tense in general because of this relationship stress, also going on to tell her how my legs and low back were the typical amount of sore due to lots of cycling.

After a little more back and forth about specifics, Emily left me to get undressed and set. I've always been fully nude during the massages, and she's very professional about draping and keeping everything covered. After getting undressed and folding my clothes onto the side bench, I climbed up on the table and laid under the heavy sheet face down. After a few minutes of focusing on relaxing my breathing and settling in, Emily knocked on the door and softly came in.

Like usual she dimmed the lights and started playing some soft background music, then started to go into her typical warmup massage flow. She always starts with some gentle pressing over the sheets, I think feeling for any obvious excess tension and grounding me into the table. Slowly she transitioned into some light head and neck massaging, then slid the sheet down to my waist to work on my shoulders and low back. By all accounts it was her typical amazing massage that I've gotten used to, and within no time I was in a deep state of relaxation.

After working through my entire back, she placed a heavy warming pillow on my neck, pulled the sheets back up, then moved to my lower half. Undraping one leg at a time, she worked upwards from my feet to my glutes. She made a few comments on how tense my legs were, and probably spent a good fifteen minutes on each leg. My hamstrings and glutes were especially tight, and she ended up working out a couple deep knots right at the top of my hamstrings.

While she was working on this area, she ever so slightly spread my legs further apart. Her hands would drift slightly up the inside of my thighs at the top of each stroke before wrapping around the bottom of my glutes to my outer hip. She was also using slightly more pressure than she typically does. While none of this on its own was unusual for a session with her, the combination of high inner thigh work, deep hamstring pressure, and her hands working firmly into my glutes pressing my hips into the table was causing some extra sensation in my groin.

I got a brief respite when she switched to my left leg, but after she worked her way up and repeated the same thing on the opposite side, I was decently hard, my erection pressing into my lower abdomen. It wasn't the first time I had gotten physically aroused during one of her massages, but it's not a typical occurrence by any means as I'm usually so relaxed and "out of it".

Thankfully though after she finished working on my legs she covered me back up fully and massaged my scalp for a few minutes before having me flip over. During this time I was able to recenter my breathing and let myself calm down a bit before flipping over.

After adjusting the pillow supporting my leg and removing the headrest from the table, Emily said she thought it'd be best if she skipped massaging my arms or chest and spent the rest of the time working on my lower half given how tense it was. I readily agreed, and after repeating the same grounding touching routine through the sheet, she moved down to my feet and uncovered my left leg. It felt like she moved a little slower than usual as she tucked the sheet beneath my leg, her long fingers delicately tucking it beneath the opposite thigh. While my eyes were closed and I couldn't see, when she got closer to my groin it felt like she left the sheet a little looser than normal and slightly higher up, right at the crease of my inner thigh.

She massaged my left foot for a few minutes again, working around my ankle and calf, then up to around my knee. She used some deep pressure on a few tense spots in my quads right above my knee, then repeated a slow stroking motion using deep pressure in her fingers up and down the center of my thigh. My hip flexor was especially tight, and she transitioned into massaging it with her palm/wrist. She was standing on my side and her fingers were pointing in towards my crotch as she did this technique.

Again, this isn't necessarily out of the ordinary, but something felt ever so slightly different and I was now very aware of her fingertips as they occasionally grazed my inner thigh, right at the crease of my covered groin. A few times as she started to work around the top of my thigh and hip it felt as if her fingernails barely slipped beneath the sheet, a slight tickle against the soft skin of my lower abdomen and top of my groin. I should mention that I keep myself fairly trimmed, not fully shaven, but very short. On one of these passes of her massaging hand, the tips of her fingers definitively slipped under the sheet and grazed my trimmed pubic hair, causing me to breathe out deeply and instinctively flex my hips slightly.

I also heard her let out a deep breath/sigh. Now hyper aware of every movement of her hand and fingers, I started to become aroused again. After that initial graze she transitioned slightly lower down my thigh, still working deep along my inner thigh but not as close to my groin. Regardless, the deep slow pressure from her fingers caused me to get very hard. Like I said this wasn't a first, but mixed with what seemed to be some sexual tension it felt different.

Emily noticed my erection pressing into the sheet, and unlike the previous few times it happened commented, saying in a slightly playful tone "I'm glad your legs seem to finally be relaxing, your hips were the tightest I've ever felt them."

I responded, my voice slightly raspy, saying something along the lines of "yeah I didn't even know how tense I was, this feels amazing".

She laughed, and then confirmed that there definitely was some sexual tension. She was still slowly massaging my left thigh, having let up on the pressure slightly. In response, she said "Absolutely. We've definitely got the blood flowing again, so that's good." As she said this, her hands slid up my thigh and ever so slightly nudged the side of my erection, firm enough to know it was deliberate.

I let out a breathy sigh that turned into a slight laugh. I didn't know exactly what to say - I didn't know in the moment what exactly I wanted or if she was even offering something, but mentally just decided to go with the flow and let her take the lead. Wordlessly she walked back down towards my feet, loosely pulling the sheet back over my left leg. She uncovered my right leg and repeated the same slow procedure of tucking it underneath my leg.

When she got up towards my groin though, she left the sheet very loose and high. I couldn't tell exactly, but it felt like if the sheet shifted by just a hair the side of my cock would slip out and be exposed. She then dragged her nails from the bottom of my abdomen down my hip, thigh, and leg as she stepped down to my feet. On this side she spent barely a minute massaging my foot and calf, quickly returning up to the side of the table to massage my thigh.

My right leg didn't seem as tense as the left, and her touch was in turn much lighter and softer. She didn't work deeply into my hip flexor or thigh, instead making slow, gentle strokes up the outside of my thigh, rotating across my hip, then slowly down my inner leg. Again her fingers would drift underneath the sheet, this time grazing the tense skin just beside my cock, causing me to keep growing harder. We were both quiet, just the sound of our heavy breathing mixed with the background music.

She paused for a moment and I heard the cap of her oil bottle flip open, then her hands reversed their motion, starting at my inner knee, moving slowly up to my groin, then across my thigh and down the outside. Her hands were much slicker now, and with each stroke up her fingertips felt like they moved a millimeter closer and deeper. I was definitively turned on now, my cock was about as hard as it could get, and I could feel an intense throbbing and pulsing through my abdomen and hips.

My cock was pointing downwards but pressing up against the sheet, and finally on one stroke upwards her fingers made contact with the side of my shaft, about halfway up the length of my cock. I let out a soft sigh as the sexual tension broke, and her fingers slid further to the center of my cock, pressing into it and rubbing upwards towards my abdomen.

As she finished this slow oily stroke, she sighed, then leaned her head closer to me and asked in a whisper, "is this okay?"

My face felt incredibly flush and hot, my heart was beating, but instinctively I nodded and said "yes", my eyes still closed, fearing that if I opened them it would all end for some reason.

She didn't immediately accelerate things, but continued massaging up and down my leg. Now though with each pass upwards her hand would slip further and further underneath the sheet, her fingers exploring more and more of my shaft along the way. After a minute or so, she transitioned to massaging my lower abdomen, sliding her hands from my hip towards the center of my stomach, her fingers pressing into the base of my cock.

I could feel that dull throbbing heat and anticipation building rapidly in my stomach as my hips started to move slightly to meet her touch. Wordlessly she continued to move lower and lower, her hands starting to move further down with each stroke, the sides of her fingers sliding between my now throbbing balls and thighs. She wasn't just exploring with her hands either, still skillfully massaging the delicate muscles and area around my groin.

Finally after a few more agonizing minutes of this, when all I could think about was the intense pleasure coming from her fingertips, her right hand slipped under my balls and gently cupped them while her left wrapped around the base of my cock. Her firm grip around my shaft caused my erection to stand straight upwards, the sheet now fully slipping off to the side and exposing me for the first time.

In unison we both let out a quiet, soft groan. Without letting go, she leaned down towards my head again and seductively whispered "we have to stay quiet". My eyes were closed, but I could tell her lips were just an inch from my ear, the warmth from her breath radiating onto me.

While maintaining a firm grip around my shaft, she slowly started to pull her left hand up the length of my shaft. Just as her fingers reached the underside of the head of my cock, she paused, squeezed, then dragged her hand back down. She probably spent five seconds in each direction, moving her hand painfully slowly up and down, over and over again. Every sensation was so visceral and intense. In the moment, I didn't have a single thought, purely absorbed in the feeling of her oily fingers wrapped around me.

It was one of those experiences where time didn't seem real, my body felt like it was floating, all my energy concentrating directly beneath her touch. At some point she started to slowly roll my balls between the fingers of her right hand, her left still massaging it's way up and down my shaft.

On one stroke upwards, just as she paused below the ridge of the tip of my cock, she slowly slid her thumb across the smooth insanely sensitive skin of my head. I had to bite down on my lower lip to stop from moaning out as she repeated this, firmly gripping my shaft while starting to explore my head with her fingertips. Her right hand let go of my balls and moved upwards, her fingers gently caressing and stroking my tip. I could feel her spreading my precum around, mixing it with her oil soaked fingers.

For the next few minutes she freely explored my cock with her fingers, loosening her grip around my shaft, mixing in softer, faster strokes up and down while almost "tickling" it with her other hand. There were moments where her touch felt electric and like I was on the verge of cumming, and others where the intensity cooled down and I felt a deep sexual relaxation.

I don't remember every technique she worked her way through, but it felt like she was gaining control of my breathing and body through her touch. Finally after a few minutes she settled into one consistent stroke that began really amplifying the intense pressure in my lower abdomen and balls. Her right hand wrapped semi firmly around the base of my cock and would pump up and down ever so slightly. Her left hand was a little looser and faster, twisting its way up and down my shaft and head.

She would twist her fingers as she crossed the tip of my cock, causing me to shiver and breath out sharply each time. She started slowly, building up to a steady rhythm that had me deeply breathing and gripping the sheet and table with my hands. Every time I started to feel like I was reaching the point of no return, she would back off the pressure and speed just enough to calm me down. She repeated this three or four times until I was practically panting, my lower lip in a decent amount of pain from how hard I was biting it to stop from moaning.

Finally after a few minutes of this amazing agony, when I was reaching another peak and I assumed she would slow down again, she continued with her steady pace. Her hands squeezed tighter and tighter around my shaft as my abdomen tightened. I could feel so much pressure and tension building in my balls as she held a steady grip with her right hand and used her left to slowly and firmly pulse up and down, just passing over the tip of my cock with each pulse.

Within seconds my head was thrown back and my muscles tensed as my orgasm washed over me. I don't know how long it lasted, but it felt like my cock just kept spasming and shooting out ropes of cum, landing across my stomach and her hands. She continued to pulse her hands throughout the duration of my orgasm, the intensely pleasurable throbbing feeling quickly turning sensitive.

Finally when my cock had stopped throbbing, just as her touch was about to become too sensitive, she slowly let go of my cock. As it softened, she let it gently fall to the side against my hip. As I focused on letting my breathing return to normal, I felt her lean down again to my ear and whisper "looks like you needed that, just breathe for a bit".

She took a few steps away from the table, the post-orgasm clarity starting to run through me as the full weight of everything set in. I heard her open a cabinet door as she pulled out one of the small hand towels from the warmer/steamer that she usually uses on my face to end a massage. Her footsteps softly came closer back to the table as she placed a rolled up warm towel across my forehead and eyes, the lavender scent calming me slightly. She used another warm towel to wipe up the considerable amount of cum spread across my stomach and chest, slowly and sensually cleaning me with it. She also wiped off my cock, giving it a few soft strokes with her fingertips.

Once I was clean, she pulled the sheets back up over me to my shoulders, then sat in her rolling stool at the top of the table. Her fingers drifted into my hair and massaged my scalp and temples for a minute before she leaned down and whispered to me that our time was running out. Just like our usual sessions, she whispered for me to take my time getting dressed and ready and she'd be out in the lobby.

Once the door closed and she left I laid still for a moment, collecting my thoughts and breath. I felt some guilt and weird emotions, but also felt incredibly relaxed and calm at the same time. I quickly got dressed and headed out to the lobby to find her waiting behind the desk like usual, a wide grin across her face as she watched me walk towards her. I could hear one of her coworkers in their staff/break room behind her and Emily silently acknowledged that we weren't alone.

We had our usual post massage conversation where she talked about what specific areas were extra tense. Her smile grew wider as she said "and yeah, I've never felt your legs that tense before, you definitely needed that." I responded by telling her how much better I felt, both of us dancing around what had actually happened. We talked like usual about our upcoming plans, and ended our conversation by scheduling another visit, this time only a month out instead of two.

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That's it for now. I'm still not really sure how to feel about everything. Obviously it was one of the most pleasurable sexual experiences I've ever felt, amplified by the whole taboo nature of everything. I won't go into another long spiel about my emotions and feelings though as I'm sure you're not here for that. Hope you enjoyed it, I guess?