Part Time Masseuse Ch. 02

I was not sure what was on his mind really, but I said, "Often people date many, many people before they find that one person where they can be completely comfortable with each other. Often that comfort level is not easy to find, and often that lack of comfort also complicates sexual topics."

He said, "Yes, that is right."

I said, "Sometimes guys want sex before the girl is ready, depends on the individuals."

I changed the subject a little, saying, "OK, time to turn over."

I held up the towel to respect his nudity, as he flipped over to lay on his back. Once I had placed the towel to cover him, I had the surprise and no surprise. As was common, he had a bit of a bulge going. As was not so common, it appeared through the towel that he was rather well endowed.

There was another quiet period as I put oil on his chest. I asked if the light was too bright, or if he wanted a towel cover for his eyes, but he said he was fine. His eyes were open as I began.

Chris said, "On the other topic, it was never something where I was pressuring the girl."

He continued, "You are right about me being shy. So I don't get too many dates. But there have been some girls I went out with for a while and they were also interested in more to happen."

I said, "OK, I think I know where you are going. Sounds good so far. So, what is the problem?"

He said, "My equipment scares them."

I finally realized he meant that he dick size was too large.

"Oh, I see. You mean size."

"Yes."

Men seem to have a fixation on size, so I did not know if this was an exaggeration or a practical reality. This was certainly not how I expected this massage to go. However, as I had been working on his chest and stomach, I had sensed his 'growing reaction.'

Instead of working on his legs, I massaged his arms instead. I sat on the edge of the table and raised his arm, putting his hand on my shoulder as I oiled and rubbed down his arm.

I said, "I doubt there is a problem. Probably the girl is also inexperienced. Give time and some practice, I think eventually couple overcome all sorts of problems, including that one."

"Well, I sure hope so. But it has been frustrating so far."

I said, "I think most everyone your age finds sex to be a little frustrating. Give it time, I am sure it will work itself out."

I thought about it a little more, as I moved over to do his other arm. I also took another glance at the bulge under the towel and concluded he was not exaggerating about size. He appeared under the towel to be substantial. This was a total non sequitur based on his long and lean body type..

I said, "A couple of obvious things to say. I think men are generally way too focused on size. No woman is going to make a choice to be a couple with a guy based on that. Most men would be jealous of your 'problem'. I am sure this is not the first time you have heard that."

He said, "Yes, I have heard that all the time. Locker room teasing, I get it."

I continued, "The other obvious thing you should know, that maybe you have not heard, is that maybe if you are frustrated, you should consider dating older girls."

I was now working on his calves. I looked up the table at him, looking puzzled.

I said, "I don't mean my age. But I guess you are dating girls your own age. That is natural. But if you go out with girls in their late 20s or early 30s, I think you would find out they have experience and a desire to ...handle somebody like you. The girls your own age will eventually get there, but initially they are just overwhelmed. You say frightened, but maybe it is more of a intimidated feeling."

Chris said, "Thanks for your advice, but it is not as though I have had much opportunity to date older girls."

I chuckled, "Good point. Sorry, I don't mean to laugh or minimize your frustration."

He said, "I didn't take it that way. This is not a subject that comes up in normal conversation, and especially not with a woman. I appreciate that you were open to discuss."

To change the subject again, as I was working on his thighs, I asked, "Doing OK on the massage?"

He said, "Yes, this is great."

I said, "Well, I thought we had you very relaxed, but your frustration on this topic seems to have you tensed up again. Relax."

I had gotten up fairly high on his thigh, reaching under the towel. By the time I had gotten around to his other leg, I caught a look at his balls. I will just say that they were also large.

I moved back to the end of the table to stand by his head. I began to rub his temples with my fingers..."Relax".

He closed his eyes and I could feel him let go his tensions. "That's it. Good. Relax. That's better."

"Thank you."

I replied, "My pleasure. I have enjoyed meeting you, I like our discussion. Sorry that we got off onto stress creating topics."

Still standing at his head, I started rubbing his chest again, pressing down a little harder than before with my palms. I put some more oil on his chest and stomach, working it in.

While he was more relaxed now, there was at least one part that was not. It seemed he had not been erect before, the bulge had just been a sign of size. Now there was more of an unmistakable lifting.

As I leaned over to rub the oil on his stomach my own stomach had pressed against the top of his head. When I had lifted up, he had opened his eyes and was looking up at me.

"Sorry", he said.

"Sometimes that happens during a massage. Don't worry."

I moved to the edge of the table on his right side. The tip of his cock was just peaking out the towel.

I said, "Chris, that is a normal reaction during a massage. It does not always happen, but sometimes it does. We get used to it."

With that, I pulled the towel away. There is just no way to sugar coat it, he had a big cock by any measure. I would guess he was between 8 -9 inches. But he was also rather thick around.

"Chris, I can tell you for sure that 99% of men would love to be in your position. And you will be a big hit with the ladies when you find the right ladies."

He smiled, maybe a little proud with himself. Sort of like getting to show off a little without the reaction from the girls he had been with previously.

I took some oil and dripped it on him. I looked at him, as I touched him with my hand, "OK if we continue?"

He nodded his head, "That would be great."

I gave him a few strokes. He was heavy in my hand, very thick now and hard. More like 9 inches plus.

He groaned a little bit as I gave him a hand job, "Does that feel good?"

He groaned again, but of course I already knew the answer to my question. How could it not feel good?

The mischief opportunity took over as I removed my hand and said, "I don't want to get oil on my shirt".

He was staring with eyes wide open as I lifted my shirt off. My breasts were straining against my bra.

I took him back in my hand, wondering if he was going to last long before cumming.

I had not decided to give him a blowjob until that moment but leaned over to kiss the tip of his cock while I looked at him. I still had his shaft in my hand, but I did give the head some licks and kisses.

I said, "I suppose it is not easy for your girlfriends..."

I had relaxed my throat as I took him into my mouth. Probably the thickness rather than the length caused girls the most problems. I took maybe 3 inches in my mouth before backing off. Chris could not seem to believe this was happening.

I took off my bra before taking him again in my mouth. This time I was able to take about 5 inches in before reaching feeling a slight gag reflex. I felt him squeeze my breast. I looked back up at him with his cock deep in my mouth. I lifted up and smiled.

I asked, "How is that?"

Again a silly question, but interesting response, "I have not had anyone able to take me in their mouth that deep. I have seen it done on the internet, but I never thought that could happen to me."

I said, "You are really big. I cannot take all of you but let me try a little bit more."

It is always this way for me with a guy with a large cock. If I try to take too much, too soon, I get a gag reflex. If that happens, tough to avoid it from recurring. But if I am careful to avoid it, I am usually able to take a man in a little more. The problem here was not only that he was long, but also fat.

I lowered my mouth on him again, Chris caressing my breast. I went slowly, stopping to suck him at various depths. But finally, I made an effort to take him in as deep as possible. I could feel his head at the back of my throat, tried to calm my gag reflex by pausing, then taking a little more, a little more.

It is difficult to say how much of him I could take inside my mouth, but it was probably between 6 or 7 inches. Not sure if any more was possible, but that was all I could manage that day. I could not really suck him that deep, but I lifted off a little and then was able to do a little stronger sucking.

I knew I could make him cum at any time, but this was also interesting and arousing for me.

I said, "Sometime, you will have a girlfriend who is willing to practice a little when giving you a blowjob, and she will probably get better and better at it. You just need to find the right girl, then you need to have enough time together for her to have time to get used to you."

He was watching intently as I licked the head a little more. He started to smile widely. I took him a couple of inches in my mouth while sucking and stroking him with my hand.

I lifted up abruptly, saying, "OK, next bit of counsel."

I took his hand and brought it to my pussy, let him feel me through my shorts.

"I guess your next problem was that your girlfriends have either not wanted to have intercourse or didn't like it. Am I right?"

He shrugged and nodded yes.

I slipped off my shorts and panty, then let him feel me. I said, "See how wet? That happens easily for me, but not for everyone."

I was already dripping wet.

I continued, "Go ahead and slip your finger inside."

He felt my wetness and I said, "You can never try intercourse with someone as large as you without the woman being this wet. Best if it is natural this way, but if that is not happening, or for extra comfort, you should always have lubricant handy."

I licked the head of his cock again, then said, "Then I guess the next mistake is you getting on top in a missionary position..."

Now that I was also fully nude, I climbed up on the table, saying, "Much better idea is if you let her get on top like this."

I had my right knee on the table, but he was long enough that I had to raise up high enough by having my left foot flat on the table as I moved his head around my pussy lips.

I said, "This is a little bit like stretching before a workout or an athletic event. My pussy muscles will stretch out, but initially it can be a little painful. This way I get to control how much of you enters me, and how slowly, gently."

With that I slipped only the head in...slowly...then lifted off.

I said, "OK if I continue?" But of course, I already knew the answer as he nodded. I lifted his hands up to my breasts, loved the way it felt as he squeezed me without being told.

I smiled, but said, "Not too hard, be gentle. Watch for signals what she likes. Help support me now, put your hands on my ass to give me some help."

He was listening and following my directions as I slipped him in again, this time a little deeper, again slowly. Without lifting off, I sat down on him a little further.

I was loosening up without much effort but lifted off again. Not all the way, but enough so that only the head was still inside.

I lowered back down again, this time taking him about halfway. Then lifted off again. I did a few strokes at this depth of him inside me about halfway. I could tell he was thinking that maybe this was all I could take. But really now after the slow entry and the multiple strokes, I was now more ready for him and slipped down again further on the next down stroke and the even further on the next.

I paused with him in deep now, shifted my legs so that both knees were now on the table.

He had closed his eyes earlier, but as I paused now, he looked up at me. I smiled broadly and brought his hands to my breasts again.

I said, "Have you been inside anyone this deep before?"

He shook his head no, saying, "No. Never. I was wondering if I would get this chance."

I had all of him inside me know as I sat down deep on his big cock. I was of course enjoying this immensely, but I also felt some responsibility based on his limited experience. I wanted this to be nice for him also, but I thought the instruction was a bit necessary also.

I had just been sitting on him calmly but could feel his big hard cock inside me deeply. But before additional strokes, I squeezed my pussy muscles together in some pulses, squeeze, relax, squeeze, relax.

I said, "Can you feel that?"

His eyes were wider open as he nodded yes, I said, "OK, feel it now."

With that, we did some slow strokes up and down where I continued the squeeze relax. For sure I could tell he had not been in that deep inside a woman before, nor had the experience of this kind of vaginal constrictions.

I did not want him to cum yet but knew that was always possible. We did a few more strokes together before I lifted off completely. I climbed off the table, but then leaned over to suck him a couple of times before also guiding him off the table.

I said, "OK, we are going to switch positions now."

This was not the session to try a lot of positions, but I knew he had likely tried and failed to have a good missionary position experience previously. So, I laid down on the table, and pulled him up on top.

Before I let him enter me, I said, "Remember how when I was on top, that I came down on you slowly, paused, pulled out... you do that now also."

I repeated as his head touched my pussy, "Slowly and just a little bit..."

He followed that guidance and slid in a little bit. Now truth be told, I was wet enough and loose enough that I did not need this, and wanted him in deep, but that would come.

He had of course fully understood and had followed the guidance. So each time he went in a little deeper, he did it slowly, paused, pulled back. Finally, he penetrated me deep.

I said, "See, if you follow that slow and gentle process, and you are careful to let her guide you, loosen up, enjoy it; you are more likely she will want repeat sessions."

Then I continued, "Lesson over. You can go ahead and do whatever you want now. Time to enjoy yourself."

He did not need any more encouragement than that as he began to fuck me. He quickened his strokes and there was also a nice pounding as he got more confident.

I was enjoying this immensely, even approaching my own orgasm. But when he paused for a moment, I held his ass and said, "Also remember, unless you know the girl and she has told you it is OK, never cum inside her."

He nodded and said OK, then he resumed his nice stroking. He was big enough that he did not have to have too much technique to satisfy me.

I felt my orgasm coming as he was getting the hang of this. I began to groan, "Oh yes, just like that."

I had a really great orgasm. He did not pause at all, which made me have a really long and intense orgasm.

From his own pace and face expression, I did not expect him to last too much longer.

He lasted a couple more minutes, but frankly a little longer than I expected, before pulling out and shooting a big rope across my stomach.

He was groaning as he had a couple of more big spurts. I must say, he had a pretty big load. Not sure if that was normal for him or had been a while since his last time.

He was looking at me now, finally not shooting off more cum, but still a little oozing out. I guided him off the table, so he was standing, and I got off the table also and knelt down, taking him in my mouth.

He was not full hard now, but still large. I could taste him on my tongue as I sucked him gently while he began to relax. He had his hands on my head as he lightly groaned.

Finally, as he relaxed more, I looked up at him. I scooped some of his cum off my stomach as he looked at me. I lifted it up to my mouth and put it on my open tongue so he could see it. Then swallowing.

I stood up eventually. I asked, "Was that the first time you orgasmed by fucking?"

He said, "Yeah, the most before was by hand job. That was fantastic. Thank you."

I said, "I thought that was the case. It was my pleasure. You did great."

Chris said, "I never got anywhere close to that before, either on the blowjob or the fucking. Always before, the girl would always want to stop before we got very far."

"So remember, consider older girls. Go slow, let them enjoy it. Make sure you have lube, and most important, let them control it until they are ready to let you go."

I continued, "Let's get dressed, took a little longer than I expected, but in a good way. But come back again sometime and we can do it again if you like."

He said, "No problem, full understand. But I should tell you thank you, thank you. That was fantastic."

I smiled at him, but we were quiet as we got dressed.

As we started to head back to the front desk, Chris started to pull out his wallet for a tip, but I stopped him.

I smiled and said, "Save it for next time. This time was my treat."

I leaned up to give him a kiss on the cheek. He had a big grin on his face. I reached down and squeezed his cock, saying, "You better come back. You had lesson one only..."

I started to lead him out, but stopped and said, "Not a word of this to anyone please. OK?"

He nodded and agreed, "Understand, no problem."

I smiled at Chris, "Thanks Chris. See you soon."

I was exhilarated, satisfied, but also a little tired. A very eventful day so far already. But also, no signs of Bill and Stacy, but I found a curious situation at the jacuzzi where they were both lounging and relaxing. What was curious was that they had a TV sitting on a portable table where they could see it.

I walked up, "You guys look relaxed, but what gives with the TV?"

Stacy ignored the question, saying instead, "Seems like you were in there a long time..."

I smiled and said, "None of your business, you can't make me talk."

Bill answered the earlier question, "We have our cop coming by soon, just want to be able to see when he arrives."

I walked around a little to catch a glimpse of the boring parking lot on the monitor.

Right on cue, a car pulled in.

Stacy chimed in, "Good timing, here he is now."

She stood up from the jacuzzi, when I said, "You guys look very comfortable. My treat, why don't you let me handle it?"

Bill looked interested, but Stacy started to object, before I cut her off, "What's the problem, I understand, we talked about that before."

She came over to my side of the jacuzzi, whispering, "This is a big deal. We don't want any problems."

I whispered back, "Don't worry. I will make sure he leaves happy."

She still looked a little concerned, but said, this time in a normal speaking voice, "Are you sure?"

I just nodded and smiled, "You two have done a lot for me, I have really enjoyed my part-time job. Promise it will go well. I would like to do something nice for the both of you."

Bill gave a big grin, but Stacy just said, "Very nice of you. I will be right back here in case you run into any problems."

I said, "There won't be any problems, don't worry."

With that, I headed to the front desk where our policeman was just arriving. He looked a little puzzled to see me, but before he could say anything, I said, "You must be Dan, Stacy has told me a lot about you."

He still looked concerned, so I continued, "Sorry, but Stacy is not feeling well, asked if I could fill in for her."