Dared by my boyfriend

I work in a massage parlor. But hang on, already now you may think you know where this story is going, but I think you will be surprised.

First of all, I massage women. Plot twist! You didn’t see that one coming, did you?

I give a proper massage, but I am also thorough. These girls want to experience relaxation and pleasure and I know exactly how to give that to them with my hands.

I even let my body slide on theirs and the result is often that my official massage uniform becomes transparent. And I can see their hungry looks when that happens.

So yes, there is definitely a sexual component to this job, but it’s a good one and I get to give pleasure and that gives me pleasure – plus money.

I regularly give them a happy ending of sorts.

Some times it’s a new girl and I have to do some testing along the way of the message to see what kind of massage she wants. I don’t want to make any of us awkward by asking her outright.

I may do it by casually putting my hand directly on her butt and see her reaction.

Some girls don’t like to lie still while I give them their happy ending. Maybe it’s some sort of misunderstood kindness. Actually, it’s easier for both of us if they will just lie down and enjoy.

One time a girl kept talking on the phone when the hour had already started.

I got my “revenge” later by turning her on, but not finishing her off. I have some pride in my job. I am the best in the entire street.

But don’t think it’s all sex, every day. Lots of customers are not interested in that sort of thing. I just didn’t think I would spend my time telling you about those.

One girl, for example, keeps her towel on.

Of course, I do remove the towel eventually, but she keeps her legs together, and that’s a clear indicator that she is not up for any funny business. Fair enough!

It does cut into my tip somewhat, but I don’t mind. I just want the customer to be happy.

I do a little test some times. Maybe she has changed her mind.

Anyway, my work is important for you to understand my situation, but let me not bore you with any more details.

At home I have a boyfriend and we are very dedicated to each other. He knows what I do at work. And maybe that is what gives us the freedom to play some games and some times sexy games. For example, one time I surprised him by serving him a beer in this beer wench outfit, topless of course.

Another time I had this hot lingerie photo done for him. He really enjoyed that.

And that is also how a chess game ended up as something completely different.

Yes, we play chess. We are pretty much equally good at it. He wins a bit more than I do, but only because I some times let him win. I think I am actually a bit better than him.

One day he was setting the pieces up for chess and often we play for ‘dares’ and those dares are almost always about sex. I was feeling horny so I was already planning to lose quick.

“Oh, is that a new opening you practiced” I said. He nodded.

Soon after I resigned and I had to let him fondle my boobs.

“Up for another game for another dare?” he asked. “Sure, what’s the dare?” I asked. “I’ll tell you when and if I win” he said. Uhh, a mystery.

He set the pieces up again and he won shortly after. Then he told me the dare and it was something I did not expect. He asked me “do you ever massage any men at your work?”

I shook my head. “Of course not, you know that”

“Tomorrow I want you to take a booking from one of the men. I dare you!”

He explained that it would turn him on to think about it. I asked if he wouldn’t consider it cheating and he said he wouldn’t because he had asked for it and he had arranged it.

I have never declined a dare before and I was not going to this time.

We had some very hot sex that evening, thinking about what was going to happen tomorrow.

The next day I signed into work and I put my name in a different column than usual. I would be getting any gender clients and it would pretty much be guaranteed that I would get men.

“I guess I will take your shift today then” Glenda said, when she saw that I signed in on mixed. “Sure, I’m gonna see what it’s like”.

My first client was a man and I started out giving him a normal massage like I always do. When he turned around, he had a huge erection. I continued massaging him and when I got to his crotch area, I did not shy away from touching his penis. This is what my boyfriend had dared me to do.

I considered for a moment if I should give him a blowjob. I don’t know why, but whenever I see an erect penis, I guess I have been conditioned to putting it in my mouth.

However, I didn’t do it and not sure if I would have, but then the client came everywhere, even hit my clothes.

I signed out early and went home. My boyfriend and I had wilder sex than every before.

“And then what happened?” he asked and when I told him he’d cum after my barely touching his cock he was sort of disappointed.

“OK, but you know, it would be hotter if you had actually fucked him”.

I chewed on that for a while.

The Repair Man

“You know the red piece, right?” Yes, I knew.

He had bought this lingerie for me a few years before and it was a big turn-on for him.

“We need the flush fixed. Why don’t you receive the repair man wearing this while I’m at work? Would be so hot!”

Having apparently disappointed him on his previous dare, I agreed to this crazy idea. He arranged it right away for the very next morning.

My boyfriend called me from work. “OK, he’s coming now, are you ready?”

“Yes”, I lied. I couldn’t make myself receive him in just that lingerie so I wore a silk bathrobe over it and opened the door wearing that. It was hot as hell.

Once inside, I allowed my bathrobe to fall down.

I was excited to see his reaction, but he was just working on the problem.

It was a bit disappointing actually. I asked a question to make sure he saw me.

“OK, run the bath now” he said, to test the water.

That was my chance.

“OK, but I don’t want to get this wet” I said and took my lingerie off. That was bound to get his attention.

“Whoa” he just said.

I turned the water on and he confirmed. “Yes, the problem is fixed”.

“Uhh, one problem” I said “It’s charged on the creditcard and I don’t have any cash here for your tip. Come to the bedroom, your tip is in there.”

I couldn’t believe what I was saying.

In the bed room I started blowing him.

He was making sounds of pleasure and I remembered how disappointed my boyfriend had been last time when I had stopped at just a handjob, so I made sure to go all the way this time. The guy was up for it and were fucking me.

He was a gentleman and pulled out and came on my tits.

“Nice tip” he said and left.

When my boyfriend came home from work he started asking about how it went. I got as far as to the lingerie and his reaction and getting naked in the bath before he was already ripping my clothes off and fucking me.

He talked a lot about that in the following weeks and then he started setting up the pieces for chess again for another dare. I decided to let myself lose again. I just had to hear what his idea was.

The Kitchen

He was going to bring home one of his colleagues and he wanted me to be in the kitched wearing just underwear and an apron.

As I was getting ready, I was tingling all over. I realized that the apron would never cover my boobs as I had thought. I wondered if my boyfriend was aware of this or not.

As I was doing the dishes, I heard the door open and two guys come one, one of them my boyfriend, the other a voice I do not recognize. They went to the living room and sat there and talked for a while. I found it silly that I was in the kitchen doing housework half naked.

Then I hear my boyfriend tell his colleague to help himself to a beer from the fridge.

This is what he saw in the kitchen.

I acted surprised. And the colleague simply consoled me. “Oh sorry, didn’t see you there. Oh, don’t worry about that, I will be out of your hair in no time.”. Then he grabbed a bear and went back to the living room and that was it.

Yup. That was literally it. He didn’t come back. My boyfriend was somewhat disappointed.

The Calendar

A week or so later, he started talking about the calendar. He explained the wives are doing a photoshoot for the official company calendar and I just knew he wanted me to volunteer for it.

“Are the others doing it or what?”

“Are you serious? All 12 are signed up, but Jenkins is leaving the company. Don’t tell him, he doesn’t know yet. But it means one more is needed. I kind of told them you would do it”

He assured me I would be there with other wives and I knew at least that it would not be embarrassing for me as long as we were together about it.

Fast forward to the photo shoot for the calendar a few days later, and I found myself in some lingerie with two other wives in similar lingerie.

It was really quite tastefully done.

The other wives seemed to know what to do so I just went with the flow.

It was a surprise for me that it was going to be topless. I thought it would be too raunchy for a company calendar. But the two other wives helped me off with my top.

They even fondled my breasts for a bit and we all smiled and posed for the camera.

“You’re brave” the wife in the red lingerie said. “I said I didn’t dare to go topless, but you are really brave. Good for you” she said.

It turned out I was the only topless wife (even though I am actually a girlfriend) in the whole calendar. I was June.

The Personal Trainer

My boyfriend came back with another horny idea a few weeks later. “What if you went to like a personal trainer…”.

Before he could finish, I asked “Where do you get these ideas?”

He explained the whole idea. He just wanted my to have an accident and then see where that would go from there.

This guy had a gym in his house and I showed up there in a blouse that would easily become too small. That was part of the plan.

The training went fine and he was showing me how to use the different tools. Are they called tools?

As I was bouncing on the ball, as he had instructed and raising my arms, I managed to get my blouse to ride up over my tits. This was the whole point of me being there.

That clearly made him horny and perhaps that was why he arranged for the next exercise to be a little more up close and personal.

I apparently had to sit on him while I pulled myself up with the elastic thingies.

“Is it a little difficult?” he asked “Perhaps this will make it easier” he said and poured oil on my yoga pants. Logic had taken a wrong turn.

The oil made the pants break open and he was now staring directly at my pussy.

I could feel his hard cock on my stomach and I got hella horny myself.

He said the best way to motivate myself to pull harder would be by sliding up and down his cock. He didn’t really explain it, but he did demonstrate it by inserting his cock.

Not sure what squeezing my breast was supposed to do …

He came in me almost immediately.

I finished the rest of the workout without my pants on. Well, they were basically gone.

In fact, come to think of it, I didn’t bring any other pants with me. Would I have to walk home with just my blouse on?

I ended borrowing some boxer shorts from the trainer and went home in the shuttle bus with that. Awkward.

My boyfriend wanted to hear all about it and I did tell him about it, but I also toned it down a bit. I told him how I had resisted his advances, even though that was not literally very true.

He said he had a gift for me because I had been such a good sport with these things. The package was the smallest I had even seen. It was a bikini.

Show me off

We went to the beach the next day and he didn’t let me change into the bikini until we arrived. I pretty much knew what to expect and was not surprised that it was see-through.

Anyway, I was happy that he was happy, so it’s all good. And it’s not bad that he is so proud of his girlfriend that he wants to show her off.

The next weekend we went for a hike and just before that he gave me a “top” as a present. It was understood I was supposed to wear it.

It was a real head-turned both otherwise decent enough.

The next Friday there was a company party and I was wearing my red dress.

He then dared me to take my underpants off.

It was like everything nowadays was about showing me off or about sex. In any case, there are worse problems in a relationship, so I was not complaining.

And no one really saw anything at the party. It was just his and mine little secret.

The Crisis

One day my boyfriend came home and was in a serious mood.

“What is it?”

“It looks like the whole team is going to be laid off.” he said and explained they had to win this contract that they had all counted on but the customer had just backed out. He then told upper management, who had seen the calendar before, suggested that maybe I could help.

“You, as in you?” I asked, trying to clarify.

“No, as in you – they saw you in the calendar”. He explained the whole plan to me and convinced me this was the only way to save the team. My job was simply to get them back to the negotiation table.

We couldn’t get an appointment, so I simply knocked on their door and told them I had to talk with them. They got curious and listened to what I had to say.

When I mentioned I was sent by the company, his demeanor changed. He almost threw me out right away. “I am here to see if there is something we can do. Let’s talk!” I said.

I got up and as I did, I let my blouse slide to the side and exposed my world class cleavage. That got him listening.

They both got up. “I understand” he said “But we cannot do business with them. They didn’t deliver”.

I held both of them in the collar and sat down between them. “Just give them one more chance.” I said and then unzipped their pants.

They froze like deer in the headlights. Well, maybe not like deer. But I digress.

I started sucking both of them off, but of course focused on the boss. They didn’t protest and by their inaction, they were implicitly agreeing to my suggestion.

If nothing else, I was very successful, convincing them. They were both fucking me and with each thrust they were ethically more bound to give our company another chance.

One of them came in my mouth and the other in my pussy.

When they got up, we all got dressed and the boss paused for a moment.

“OK, listen … you have shown you are serious, but it’s not only up to me. We have two more partners and they need to be convinced too. I can set up a meeting …” he said.

“That’s all I’m asking. Thank you” I said, with cum dripping from my mouth.

The buttons in my blouse fell off so I had to take the bus home with my bra exposed, but my mission was accomplished. Partly, anyway. I just had to convince two more partners.

When I got home I told the good news to my boyfriend and he passed on the news to the CEO who was not told any of the details, but was ecstatic that the contract might be saved.

The very next day, they called and said the meeting was set up. I came prepared, dressed to convince them the same way I had before.

Both partners were there but there was also a photographer.

“We have to document this transaction. Both your company and our partners depend on this. Your CEO called ahead and said this had to be documented, so we’re taking photos.”

The photographer snapped some photos.

“Can we do one without the panties” the photographer asked.

I was not at all comfortable with this “evidence” but I was also not about to back out now.

“And the tits out as well – and give us a bid smile”.

I gave him a big, fake smile.

Without any pretense of negotiation and foreplay, the two other partners came out, fully ready and expected me to give them blowjobs.

In a way it was good I could skip the negotiation part because it would lead here anyway. Better to get it over with.

But there were still some surprises to come.

He oiled up his cock good and started pushing it into my ass. I was an ass virgin, but he was maybe used to it, because he patiently worked on it and after about 5 minutes, his cock was almost all the way in my ass. It hadn’t hurt much.

Then came another surprise.

With this cock buried in my ass, the other partner started fucking me in my pussy. My very first, and hopefully last, double penetration! I was almost excited to cross it off my bucket list in good conscience. I never thought I would do this after I had met my boyfriend and we decided to go steady.

They turned me around and continued.

The guy who was fucking my ass, was not really in control at this stage. He wanted to prolong it, but he couldn’t stop the fucking and he just started cumming in my ass.

The other guy continued for quite some time, until he finally pulled out and came on my tits.

The photographer, who I had forgotten all about in the mean time, wanted me to wave and smile with the cum still on my tits. I felt a bit degraded, but the mission was also accomplished.

I had saved the company and my boyfriends job.

When I got home, my boyfriend and I celebrated with champagne and I went straight to sleep. When I woke up it was clear that my boyfriend had fucked me. Too bad I didn’t wake up so I missed it.

He had gone to work and I went to take a shower.

When I came out there was one more surprise. The door bell rang.

“Hi, I’m the managing partner” the man said. I didn’t fully recognize him, but I said “Ohh, nice to meet you again”.

“Actually, we haven’t met, those wore the partners. I am the managing partner and will put the final signature on the contract.”

“I am here because I was impressed with your commitment to winning. Well done”.

“And the others told me about these knockers” he said and had suddenly pulled my tits out and was fondling them.

“Those tits work wonders on my cock” he said and pulled it out, already hard.

I understood that I apparently wasn’t done yet with getting the contract and had to take just one more for the team.

He pushed me over the kitchen table and fucked me right there.

When he was done, he put his pants back on. “Nice doing business with you”.

It had been a rough round and I was not ready for it. I went to take another shower and changed into some new clothes.

When my boyfriend came home he was happy. “We got the contract! That’s at least two more years! You’re amazing!”

The End

Got in trouble with the police

I lost my job at the massage parlor. I had not been aware that they have surveillance in the rooms and had caught me being improper with that male client a while back.

They took me to an interrogation room and wrote down my statement. They also told me I would have to stay in jail overnight and then I would be released.

After the lady took my story, I was going to be processed. The cop said he had to frisk me, but he was focusing more on my breasts than anything else.

He also checked my ass and pussy.

When he was done, he asked me whether I wanted to make a call. It would cost five dollars. I told him they had already taken all my money.

He then said he would pay it for me from his own pocket, but I would have to give him a blowjob.

I lost a lot of faith in peace officers that day.

They ended up sending me home that same evening with a warning. I told my boyfriend about it. Instead of compassion, he was just getting horny and started fucking me too. I guess it’s good that it didn’t worry him.

Post Script

My boyfriend and I kept playing naughty games with each other.

We made a quite crazy holiday photo with one of my boyfriends female colleagues from office.

He fucked his colleague too. I didn’t consider it cheating. After all I had done with other men as well. It was all in good fun. Although I would have preferred if we could have talked about it before.

Whenever we had sex, my boyfriend liked to take a picture of me. He liked it if I smiled and gave a thumbs up. Funny tradition.

I learned that he was showing these photos to his colleagues. Made me a bit annoyed, but on the other hand, they had all seen me topless and they probably all knew what I had done to win that contract.

We still played crazy pranks on each other. Well, to be honest, most of the pranks and dares was on me. One of the craziest dares was with one of those silly queens soldiers when we were in London.

A couple of times after that, I was asked to do some more favors to the company. One time I had to meet some executive requiring convincing at his hotel room where he had a big bathtub.

He fucked me in there.

My boyfriend liked it, so that’s something.

He said to even it out, though, he had a visit from his colleague and they were having sex at the same time. Balanced, in a way, I guess.

It wasn’t long after that I got some good news and some bad news. My boyfriend said we had grown apart as of late and he would break up with me. But he had some good news as well. A position had become available for me in the company.

With nowhere else to go, I accepted the offer.

I only worked a few days a week, but then I got sent to someone’s house and had to fuck them. Usually some rich dude. Probably needed to sign a contract.

Some times there was nothing to do a week, then they had me go to the employee of the month and have sex with him.

And after the 2 years was up, obviously I had to get the contract renewed with the partners of the other firm.

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