“You know, you’re not supposed to say ‘masseuse’ anymore.”
“Really? Why?”
“It’s associated with sex work.”
“Oh…”
When I was 20-years-old, I had probably the hottest sexual experience of my life. I was still living around my hometown at the time. Honestly, I was a bit of a loser. I knew I wanted to go out and chase my dreams, but for some reason I couldn’t find the motivation to do it. I was stuck and it felt like I was never going to get out. I spent a lot of time at home during this time. My mom was the type of person who never wanted to make anyone feel bad, which is very sweet of her, but also not the best parenting technique. She was telling me all the things I wanted to hear instead of telling me what I needed to hear, which was, “GROW THE FUCK UP! STOP TALKING ABOUT THINGS AND ACTUALLY DO THEM!”
She never told me that, but I did hear it from someone else. My mom had a friend named Christine, and she was pretty much the opposite of my mom. Christine was outgoing, loud and opinionated. I never understood their friendship. Maybe they balanced each other out? Not sure. Christine was 41-years-old, and she looked a little older than that. She wasn’t in shape, but she wasn’t overweight either. She had a very average body with an above average smile and personality. She also wasn’t a fan of bras. Her tits were always swinging around underneath her shirt. My mom would give her shit about it all the time. Safe to say, when I was a horny teen, I busted lots of loads thinking about Christine.
By the time I was 20, Christine had turned into more of a crazy aunt, so I wasn’t thinking about her sexually as much. She was there to give me advice on things I couldn’t talk to my mom about. We didn’t talk a lot, but I always enjoyed it when we did. Christine lived with her ex-husband (long story) and ran a massage business from her home. She had been a massage therapist for as long as I had known her. That’s probably what fueled the fantasies when I was younger.
I had always thought about asking her for a massage, but never did because I thought it might be a little weird. I had never had a professional massage before, so I didn’t exactly know how it worked. Underwear on? Underwear off? And what happens if you accidentally get hard? Does the massage stop abruptly? Do two burly security guards bust through the door and drag you out of the establishment by your ear? And then you’re just standing outside with no pants and a super confused erection? I don’t know. It all seemed so complicated.
But as I mentioned above, I was a pretty stressed 20-year-old, and I think Christine could tell. I was doing laundry at my mom’s house one day (I told you I was a loser) and Christine was there helping my mom get ready for a garage sale. The washing machine and dryer were right by the garage door. As I was moving my clothes from the washer to dryer, I groaned a bit and started rubbing my lower back.
“You okay?” Christine asked.
“Yeah. Just getting old,” I said jokingly.
“Oh, please. You don’t know old,” she paused, “But if your back is giving you trouble, you know I can help with that.”
“It wouldn’t be weird?”
“What? Why would it be weird?”
“I…I don’t know. I guess it wouldn’t be,” I stammered.
“If it is weird, it’ll be because of your weird ass,” my mom walked behind her as she talked, “Where did you go wrong with him” she asked her. My mom laughed and went out to the garage. “Stop by my house tomorrow afternoon. I’ll hook you up,” Christine said before following my mom out.
Well, okay then. I was about to get my first massage from a family friend. A family friend who I fantasized about regularly when I was younger. WHAT COULD GO WRONG? I had so many thoughts going on in my head, and most of them were, “What is your fucking problem? Why does everything have to be sexual? She’s trying to do you a favor! This is why men are disgusting creatures!” It was a lot for my 20-year-old brain to handle. Eventually, I was able to calm down my dick and think with my mind. By the time I arrived at her home the next afternoon, I was genuinely just excited to get some relief from the back pain.
But the dirty thoughts didn’t stay gone long. After Christine let me inside, I saw her little setup: a massage table, some music playing, towels, etc. I said, “Wow. This is my first time seeing you in your masseuse world.” That’s when she replied with…
“You know, you’re not supposed to say ‘masseuse’ anymore.”
“Really? Why?”
“It’s associated with sex work.”
“Oh…”
Great. I was thinking about sex again. Christine told me to get undressed, “Yes. Even your underwear,” while she went to the back room to grab some oils. I took off my pants and thought about if I could quickly run to the bathroom to rub one out in order to help prevent against any unwanted erections. I heard her coming back down the hallway though, so I quickly wrapped a towel around my waist.
“Get comfortable,” she told me, motioning toward the table. I went down face first on the table and tried my best to relax.
“So have you ever had a massage before?”
“Not professionally, no.”
“Tara?” she asked. Tara was the name of a girlfriend I had the year before.
“Yeah,” I laughed.
“Well, no offense to Tara, but this massage is going to feel so much better.”
I let out a little bit of a, “Oooh” as Christine placed her warm hands against my back. She poured a generous amount of oil on my back and started working her hands against my skin. I’m not sure what the technical words are to describe the hand movements of a ~massage therapist~, but she was making them. At times it felt like her hands were simply gliding around my back, moving across every muscle with just the right amount of firmness. And at other times, it felt like she was trying to dig out my kidneys and sell them on the black market. It felt good, but also painful.
After working my back and shoulders, she started massaging my legs. She started at my feet and then worked her way up to my thighs. That’s when I first started feeling the erection coming. She was working her magic on my thighs, getting close enough to my dick that it started to prepare for company.
And then she said it, “Turn over,” ahhhh, fuck! Really? Right now? I hesitated for a moment and then turned around slowly, hoping my erection wasn’t too noticeable. It was. I don’t think I have a HUGE dick (you can go through my post history to see for yourself) but it’s big enough to notice, you know? It can’t just chill under a thin towel and not be seen. Thankfully, Christine pretended not to notice. I’m sure she’s experienced an accidental erection or two before, although, I had to imagine this one was especially weird for her. She brought her hands up to my chest and pressed her palms into me. She was more gentle on my chest than my back. This portion of the massage felt very relaxing, almost like a significant other just rubbing you gently as you watch TV or something.
Because of the extreme relaxation and the fact that her boobs were just swaying under her shirt right in front of me, the erection did not falter. If anything, it became more powerful. While rubbing my chest, Christine’s elbows started to knock against my towel-covered cock. I thought it was an accident the first three times, but then the knocking became constant. It was more like a rubbing/pressing feeling now. She was definitely feeling the length of my cock with her elbows.
She must have noticed the absolute panic in my eyes, ’cause she said, “Just relax,” in a soothing tone before sliding her hand underneath the towel and wrapping her oil-covered hand around my cock. I can’t really describe how incredible that first touch was. I can only imagine it’s comparable to winning the lottery, then finding out that scientists developed a pill that lets you live forever and thanks to your recent winnings, you can actually afford to take it, and then you discover that the side effects of the pill are extreme muscle growth and controllable erections. That’s how good it felt.
I moaned.
“It’s okay, baby. Relax for me,” Christine said as she SLOWLY stroked my cock. We’re talking almost painfully slow. She looked at me while she gently stroked me. Christine smiled and pulled down the straps of her top, revealing her tits. She leaned forward a bit, and with her free hand she cupped her breast and held it right in front of me. I opened my mouth and started kissing and sucking on her nipple. She titled her head back and dropped her hand down to my balls. She massaged them as my cock twitched right above her hand. I slid my tongue out and moved it in circles around her nipple, “mmm,” she moaned.
She brought her hand back to my cock and rubbed the head of it against her palm, “I need you to cum for me,” she whispered as she pulled herself away from my mouth and then pulled down the towel to reveal my cock for the first time. She leaned close to it with her mouth, but never actually let her lips touch it. Instead, she gently blew on the head as she stroked the shaft.
“Fuck. I’m gonna cum,” I warned her. I held the sides of the table as the powerful eruption came. She pulled her head back a bit and allowed the cum to shoot all over my stomach and chest. She stroked/massaged every last drop of cum out of my dick and then stroked some more until it softened in her hand. She smiled at me and then grabbed a clean towel from a side table.
“Clean up and we’ll grab a late lunch,” she said, as if she didn’t just give me the best handjob of my life. We went out to eat at a IHOP, because we’re classy as fuck, and she did not allow me to talk about what happened. When I started steering the conversation that way, she said, “You have to just learn to let things go and enjoy things for what they are,” this started her rant/motivational speech directed at me. It’s been six years, so I can’t remember it word for word, but basically she was telling me that she believed I could do whatever I wanted, but it’s not going to just come to me. You have to work for it, and if you just waste your life thinking about everything, you’ll never actually do anything.
So yeah, she basically changed my life that day.
Source: reddit.com/r/gonewildstories/comments/axbnzq/mf_all_stories_have_a_happy_ending_my_moms_friend
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Nice story. Did you guys do anything more after that?
Wild. Wow..
Did she ever tell you if it all was part of some strategy? Did she plan anything out or was the whole thing spontaneous on her part?
So you’re saying there’s a sequel…
God damn dude, you are really good at writing exposition in a smut story. You have a natural handle on something that a lot of writers really struggle with.
Awesome!