Amateur Masseur Ch. 01

A man pretends and unselfishly gives a woman new pleasure.

Anonymous Robin

2019

We were spending a week at an offshore resort. It wasn't one of the crazy party places. More of a tame beach club catering to couples and groups of friends. The guests seemed to fall into a few camps. Some were newlyweds on their honeymoon. Another camp for couples tended to be married with kids. Like my wife and I, this was just the easiest option to take a week's vacation and leave the kids with the grandparents.

A third profile were several groups of non-couple friends. These tended to be groups of single women. Women have the luxury to enjoy a calm beach vacation together whereas men often choose more active adventures.

My wife and I are quite comfortable together. Over the years we have opened up our relationship pretty far. We have never agreed to full swinging but have enjoyed watching and encouraging each other in strong flirting. In several situations we each experienced some heavy naked touching by friends in the hot tub. We found a level of pleasure in watching each other receiving sexual pleasure, just for pleasure's sake.

Sitting on the beach at the beginning of the week we laughed at the innocence of the young women and couples. We'd secretly listen to conversations around us and take notes on what they were saying and how we thought it differed from what they were thinking. The women often tried to share previous wild experiences but their stories seemed somewhat tame. Either they were lying and rounding down the truth to keep their reputations, or they really hadn't experienced much yet.

With the population of women disproportional to men, I had the luxury of sexy people watching at the beach. My wife and I would jointly comment on the beautiful women's bodies. After I made enough comments detailing my attraction to a few, my wife offered me the freedom to practice some pickup attempts. There were fewer choices for her to investigate single men yet she found it exciting to watch me in action. She was obviously the beneficiary later of any excitement I might create.

Mostly it was just fun fantasizing. But with freedom comes creativity.

On the third day, the groups of women finally got tired of sitting around talking and started breaking up into smaller groups to explore more activities. During one evening my wife and I were checking out the facilities looking for extra towels. We found the spa unlocked after closing hours. Sometimes just being in the right place at the right time is all that it takes. We weren't too worried about getting into trouble as we turned on the lights and looked around. While we were grabbing towels two young ladies walked in asking about massages. I immediately without thinking informed them the place was closed which should have ended any possibility of fun. The women started to leave until my wife's quick thinking came into action.

"The professional hours are indeed closed but John here is available. He is on staff but since he isn't fully licensed he can't get paid for yet." My wife was smooth.

"So you two work here?" asked one of the women.

"Yes, I am just seasonal so I help with general staff work during the busy weeks. John, is this your first season at the resort?" This was her way of handing the attention back to me.

"Yes, I am basically scheduling help while I study massage therapy in Miami." This was the best I could do without cracking a smile. The key was for us not to present ourselves as a couple but just two off-shift workers.

"So, are you open or closed?" The second girl sounded a bit skeptical.

And here was my brilliance taking the lead from my wife. "I am staffing this portion of the spa for a few hours each evening. Since I am not licensed I cannot charge for my services. The resort lets me use this facility after hours to acquire practice times which count towards my certification." I had no idea if anything I said was accurate or believable.

The first woman was still interested even though her friend wasn't fully satisfied. "So I can get a massage and it won't cost me anything? There is a dental school near our home that gives free cleanings for the same reason. I guess everyone needs to learn somehow." She seemed both innocent and cheap.

My wife kept adding validity. "So if one of you is interested I will finish cleaning and let John get to work. The other can come back later to see if John wants more than one session tonight." It appeared she wanted to separate the two women and hand me a naked body to enjoy. She avoided eye contact but she seemed quite pleased with the situation.

The two women whispered for a bit and it appeared the second one wanted to pull her friend away to other activities. I interjected, "So who wants to go first. Have you been to professional massage therapists in your past?" I really tried to sound professional and persuasive at the same time.

"I haven't but my mother swears by them. I was hoping to get a massage this week but the prices seemed really high." Wow, she sounds really inexperienced the more she talks.

"Ok, let's get you started. You can choose a 30, 45, or 60 minutes session. What did you say your name was?" At this point, I was physically trying to separate the two friends. My wife began talking to the second friend as a diversion.

"I guess I can go find the others. I probably won't want one but I can come to get you later. Are you sure you will be OK?" The second friend tried to instill caution.

"Oh, she will love it. John is quite calming. Just let us know where you and your friends are and I am sure John can deliver her when he closes up." My wife is really something.

"I will be OK. I think they were playing around the badminton course. I'll meet you all back at the dinner entrance later. It will be fun. I can't believe I will get a free massage!" She almost squealed.

"OK, but come find us if you need anything." The friend was practically pushed out through the doors by my wife. Now I am alone with a soon to be naked young lady.

"So why don't we start with a simple 30 minute session and see if you want more. It will be quite relaxing and feels longer than you think." I have had my fair number of massages and my wife and I of course include massages in our sexual play. But I have never actually pretended to be a professional before. The thought of more than 30 minutes terrified me. My wife is gone and I was totally alone in this charade.

"Well, what do I do?" the woman asked.

"Take this towel. You can undress behind that screen over there. Since we are actually closed you can simply leave your clothes on the bench." The locker rooms were closed and I was scanning the room for options.

"Soooo, I should remove everything?" Her voice was quiet almost like she was embarrassed. She finally realized she didn't know what she was actually asking for.

"Yes, the towel is large enough to remain modest" I was hoping at least until she was comfortable. "Just wrap it under your arms and come back to the table. But yes, remove all of your clothing." I spoke slowly to give assurance and trust. I should have taken up acting.

"Well, OK. I don't think I have ever actually been naked in front of anyone before. Not even my doctor completely." She was trying to convince herself so I remained silent. "OK, this should be fun. I guess you know what you are doing."

I returned to the nearest table to see if supplies were available. She eventually walked out from behind the screen with the towel wrapped around her body. I think she talked non-stop while she was undressing out of nervousness but it wasn't directed at me so I didn't need to respond.

"Now what?"

"Come lie down on this table. While it is normal to start face down, I am going to try a non-standard approach. Let's start with you on your back. But I will ask you to turn over twice so that you will end face up again. I will look away while you get on the table; just drape the towel over your top." My looking away gave her more comfort.

"Ok, I am ready. I thought I would be more nervous only covered in a towel but you're really good." When I turned around she was perfectly still. Her form was magnificent. This was the first time I truly examined her body. She must be in her early twenties. Her legs were amazing and smooth. And even lying on her back her breasts were standing tall. They weren't exactly large but the shape was exquisite. I recognized her now from the beach.

I clicked on some soft relaxation music. "OK, you are free to simply be quiet and calm, or you can talk. I will respond but won't initiate a conversation. It is all part of your mind and body relaxing together." I didn't even know what I was saying but it all sounded familiar from being on the table myself. "I will just give you light and long touches for a few minutes and then have you turn over."

I started at her feet. Only a few times did she jump from being tickled but otherwise, I made my way up the legs. To ensure she didn't get nervous I didn't move past the calves at this time. Instead, I jumped from the calves to the hands and arms; lightly caressing each side. I spent some time on the hands and fingers as a way to start slowly. Then I moved to the head. From the top of her head, the breasts really took on a life of their own. My optimism around those breasts getting exposed was growing.

"Am I doing this right? Am I still covered properly? I don't know what is appropriate and don't want to interfere with your training." She started to get anxious and needed reassurance.

"Yes, you are doing great. Nothing you do will harm me. These sessions are all about you and you alone. If it feels good and natural to you then you can ask for more." I just gave her a license to be self-indulgent. And it worked, she calmed down.

Since I didn't want to cause alarm on the top of her chest I kept my hands away at this time. Instead, I massaged her hair, the back of her neck, and a really cool trick of pushing my hands under her back and pulling my hands out. I had this done to me once and it was awesome. I rotated between her head, neck, and under her back several times. She assisted with lifting her shoulder blades to get my hands under her back quite far. Her arching back created a beautiful view and I was really excited at this point. I wasn't wearing the correct shorts and hoped she didn't open her eyes to see my physical excitement. It would have scared her for sure.

"This is amazing. It is everything I wanted this week. None of my boyfriends ever gave me anything like this." She just couldn't stop talking.

"OK, it is time to turn over now." I wanted to pull the towel lower soon. "I will hold the towel while you turn away from me. This will keep you covered." She followed my directions perfectly and was now on her stomach. She repositioned a few times and I caught very small glimpses of more skin.

Now I wanted to begin some investigation and make suggestive comments. I returned to her legs. "I am sure you had lots of solid boyfriends in college. I bet you were quite studious."

"I didn't go to college. My parents didn't have a lot of money and I had a serious boyfriend that didn't want me to leave town. I guess I missed some good parties."

"So what happened to the boyfriend?"

"He got really jealous and I finally called it off. Guess I should have done that years earlier."

"So how many boyfriends have given you full-body massages?" I tried taking this to a more intimate conversation.

"Well, not really any. You may be touching me more than anyone before." (and I haven't even got started yet) "I don't mean I am innocent. I'm not a virgin or anything. But let's just say I wasn't all that comfortable and no one actually cared to make me feel special. It always seemed pretty selfish for the guys. I guess I just don't know how to pick them."

"It must be how you pick them. I am sure you are aware of just how beautiful you are."

"How can a girl really know. Guys just want to get themselves off and have girls hang on them." She was being quite free with the stories.

"Here and now you are allowed to ask for anything you want. This is your time and yours alone." I was feeding her encouragement to explore. I learned enough about her to want to give her more confidence. I moved up to the head and neck. "I'm hoping to give people like you more self-pleasure through massage." I might have gone too far with that one. "If you only knew your potential you would never have to endure those feelings again."

She relaxed but was clearly contemplating something.

"Now you need to tell me what you are comfortable with. I am going to move down your back and lower the towel. OK?"

I left room for objections but also led her into the desired position. "um, ok, I can't believe how comfortable I am. I don't remember having been this naked with the lights on."

"Seriously, you have full privacy here" I wanted to give some serious confidence to this girl, "You have a body to be proud of. Have some confidence while you are still young. The feelings you create about yourself today will last a lifetime. If you hide ashamed now you will always hide and feel ashamed. Please give yourself the freedom to respect your body."

While I wanted to enjoy her body from the beginning, now I just wanted her to enjoy her body for her own good.

"You are amazingly supportive. I thought I would be more nervous but I feel great."

I really worked her back and started moving under her towel onto her butt. She started to moan slightly and I am pretty sure at this time that I started smelling her getting excited.

"um, will you tell me if I, um, should do something or be a certain way?" This confirmed my suspicion that she is feeling excited. I moved to her legs and started coming up her thighs. "If I can be honest, I have always wanted to be more sexually free. My friends that went to college have wild stories. The boys left at home were so unimaginative."

"You are doing great. As long as you are relaxed, comfortable, and feeling good, you are doing everything right. This session is all about you and your enjoyment. Don't talk yourself out of anything." At this time I am coming right up to her pussy and just glancing along the edge before sliding up to her butt from the legs. I started using lotion as soon as I got her on her stomach. "I will periodically lift your towel from one side to the other to work into the gluteal muscles. Just remain receptive and enjoy the feeling." She was fully lubed inside and out at this time.

"How much enjoyment is too much?" She asked inquisitively. It wasn't shyness or embarrassment. It was more of an actual question.

"Since I am not on company time we have a lot of freedom. I am one of the creative boys you didn't have at home so just ask without hesitation. Everything is private here." This may have been too inviting but it felt like she was asking for something. "Eventually you will turn over again but I will continue however you direct." I started at the top of her head, massaged her hair, neck, back, and buttocks. Then returned to the legs and worked back up to her pussy.

"Well, I was just asking because some of your touches are amazing. And if I ask for more of something I didn't want to conflict with your schooling restrictions. I know there are other types of massages guys get that aren't available for ladies." She kinda laughed a bit to relieve some tension.

Did she know more than she presented? I considered her question an invitation for more options. "What you hear about guys having happy endings massages is not just for guys. Those are available for women too." I paused for contemplation. "You have total freedom to ask for anything. I am under no restrictions. Both of us can say no to anything but only you can ask."

I immediately took up the hint and pushed up the thigh towards the crotch. "Don't worry about me. I am allowed to meet your desires." My precum is practically making a spot on my shorts at this point. "Do you want me to continue touching higher?" And with this, I allowed my thumbs to rub her lips while my hands cupped her full buttocks. She breathed in and held her breath.

"Yes, if that is ok, I have never had anyone touch me so softly yet so intimate. Are you sure this is OK?"

"Please accept this today. And stop questioning yourself." I kept one hand between her legs, fingers not in but more on her lips while my other hand was giving her a head massage. Now she was totally wet.

"If you are serious, I did have a girlfriend tell me about, well, a boy that massaged her to orgasm. Not that I am asking for that, that would be wrong here, but it was something I always hoped a boyfriend would try sometime."

Something about being naked on a table with your eyes closed allows people to be completely honest. "That isn't wrong to ask for and can be offered if you ask. But you must ask as I can't push you into anything." I couldn't be more inviting.

"I guess I can say no anytime. But yes, I am enjoying your hands a lot." She breathed deeper as she was accepting the possibilities. "I would like more touch, you know there, if that is really an option."

I moved lower and pressed my hands up the back of her legs pulling them slightly apart. My thumbs went further between the legs onto her receptive pussy. "I just want one more confirmation, are you requesting this." My thumbs pressed lightly into her pussy pausing for a reply."

"Yes, I am. God I hope this is OK but yes. Whatever you can or want to do." my thumbs at this point were really deeper as she lifted up her hips in response. "I always felt more interested; wanted to be freer. [all sorts of sighing and moaning]. I knew there should be more fun to sex."

I kept one thumb pressing deep and sliding in and out while my other hand explored her other sensitive areas. Her ass was firm and grab-worthy. Nearly everywhere I touched gave her shivers. She was really enjoying this.

When she seemed to stop accelerating I transitioned her for more. "I'd like you to turn over. Please keep your eyes closed and trust the freedom and control that you have." She turned over as if I were commanding her will. She raised her hands behind her head. I lowered the towel and she didn't even notice. Her breasts were absolutely stunning. An artist couldn't have created better images of perfection. Her stomach was flat and strong. The entire body was lean and engaged.

My hands pulled her arms upward stretching her body length. I massaged her palms, moving down to her sides caressing her breasts. I lotioned her neck onto her chest. My one hand slid down her stomach and onto her pussy while the second hand massaged her breasts. She entered a trance and moaned. Keeping her eyes closed she stopped trying to talk and accepted all of the senses. My fingers entered her pussy for the first full time from the front. Her back arched, dropping the towel to the floor. I switched hands so one was massaging the legs while the fingers of the other pressed deeper, exploring her various nerves. I switched hands again to give more sensation to the head and breasts. My hand was totally fucking her pussy now as she was reaching higher.

"Please let me just touch you. I will keep my eyes shut but I want to..." she trailed off unhearable. "I need, want, something with my hand." She reached over and rubbed down my pants. I quickly helped unbutton the top and my dick jumped out. She just grabbed and held my cock while I moved both hands onto her pussy. One hand pushing fingers inside while the other massaged her clit. And then she arched higher and higher, holding her breath until she came. Fluid, heat, tight muscles, and pure enjoyment all spilled out of her body. It lasted as long as she could hold her breath, and then she returned back to lying on the table. Her incredible body naked for my pure visual enjoyment. She dropped her hand to her side and just sighed with ecstasy.