True Massage Parlor Story Chapter 1 - Steph and My First Assjob

I’ve been going to local massage parlors a couple times a year for a while and my experiences have generally been good. I’ll never forget my first time. I was much younger, probably early 40’s and used to cum pretty quickly back then and I had an older girl who was kind of a plumper with nice tits. She massaged me for a bit and I really didn’t know how to ask her to jack me off but eventually she asked if I was interested in something else. I said yes and she started to jack off my eight inch cock. As was normal back then I had a huge orgasm after a couple minutes and she said, “Oh my that was fast.” I still had a lot of time left so she continued to massage my front and occasionally rubbed against my cock which started to get me hard again. She said, “Wow, it looks like your ready to go again. I can’t remember when I made a guy cum twice in 45 minutes.” She started to stroke my cock and I asked if I could fuck her tits. She wanted more money for that but all I had on me was ten dollars. She told me it was OK because I was so cute. I fucked her tits for a while but really like getting jacked off so I had her finish with a hand job. I shot another huge load straight up in the air and she cried out in surprise and said, “Man you are a stud. That was a real toe curler.”

As with this first experience the girls are always nice and I get to do things that I don't get to do with my wife. The challenge in the past was sometimes girls are willing and not so hot or hot and not overly willing. When I first started going I thought all I could get was a hand job but over the years I learned that you can pretty much get whatever you are willing to pay for. So I’ve had blowjobs, assjobs (my favorite), tit fuck, hand jobs and even fucked girls. In case you’re wondering, I also learned that they appreciate it when I take the time to make them cum. I’ve brought these women to orgasm by fingering or licking their clit and a couple times while I fucked them. I must be bigger than most men because they always comment on my size as they jack me off, suck my cock or fuck me with their hot pussies.

I live in a smallish town in Pennsylvania and the number of massage parlors has grown over the years. I have personally visited four but my favorite is Katie’s because it’s in a location that is fairly discrete and the girls are usually pretty hot and always willing to accommodate my various fetishes. My finances are solid so I always make sure to bring $300 with me which covers massage time and tip. It’s likely that I am overpaying but given what these girls do for a living I have no problem with that.

As I wrote earlier, I had been going to massage parlors for years and I assumed that the only things that would happen would be a hand job or a tittle fuck. While those are great and I always shoot massive loads, I finally worked up the nerve to ask a girl to let me slide my dick between her ass cheeks. I have a major fetish when it comes to women’s asses and longed to rub my cock between a nice pair of ass cheeks for years. There are some great assjob compilations on the various porn sites and I usually gravitate to those when I’m jacking off. I also like videos where one guy does multiple girls and he takes them from behind one at a time. I would so love to be able to do that one day but I’ve had the pleasure of rubbing my cock on hot asses many times at the massage parlor.

Since I’m married with kids my opportunities to do this are limited so this happened when I visited Katie’s before work. The day before I told my boss that I had a doctor’s appointment and wouldn’t be in until 10AM so I left my house at 7 which I knew would leave me plenty of time for fun.

When I got to Katie’s I paid for 45 minutes which cost $60 and I had my choice of several girls but when Steph came out my heart nearly stopped. She was in her 20’s, around 5 foot 6 and just a little bit on the plump side. She was in no way overweight but her curves were in all the right places. She was quite a pretty brunette but one look at her tits and ass I knew I had to have her and this was going to be the day I’d find out if I could do it or not.

After I picked her she took me back to a room, told me to get comfortable and that she’d be right back. I would guess that the girls do this as a test against entrapment as I’m sure a cop would not be able to get naked of his own accord. Regardless I quickly shed my clothes, got on the bed and started to stroke my cock while I waited. The rooms at Katies are small and dimly lit but they all have mirrors next to the bed. This is awesome because I love watching the girls jack me off and suck my cock like I’m in my very own porno.

After a few minutes Steph was back but she didn’t comment on my raging hard on and instead asked me to get on my back. I said, “Listen Steph, I don’t come here for massages, I come here to get this big dick off. There are several things I need from you today and I’m willing to pay you well if you’re willing.”

As I continued stroking my cock she said, “OK but you realize that you need to ask me right?”

“Of course,” I said. “What I want from you ultimately is to let me rub my cock between your beautiful ass cheeks. I’ll probably want to fuck your tits and massage your entire body as well. Of course you will need to make me cum and for that I’ll pay you $150 in advance. If you make me really happy I can pay you more after.”

She said, “That will all be fine with me. I’ve never had a guy rub his cock on my ass before so I’m kind of curious. It helps that you’re a very handsome man and have a really nice cock. A lot of guys who come here are slobs and disgusting. Tell me your name and help me get these clothes off. This bra has a broken wire and it’s killing me.”

I laughed and said, “I’m Tony and I will be happy to rid you of your clothes and that horrible bra. It’s a crying shame that your beautiful tits should ever experience any discomfort so I’ll make sure to work on that for you and like I said, if you give me a mind blowing orgasm I’ll give you extra money so you can get new bras for those nice tits.”

“Sounds good to me.” She took off her shirt and shorts and turned around so I could unsnap her bra. I had to get off the bed and while her back was turned I also slid her panties off her body and held my face by her ass so I could take in her scent. Her ass was perfectly apple shaped and had plenty of soft flesh that I immediately reached out to feel.

I said, “Oh my God Steph you have the most perfect ass I’ve ever seen. If I wasn’t already married I would propose to you on the spot.”

She giggled and said, “I’m glad you like it now get on the bed and let me take care of you.” As she turned around I got my first look at her tits which were just as perfect as her ass. They were every bit a D cup and they looked really soft with just a little sag to them. Her areola were light brown and a little bigger than quarter sized and I couldn’t wait to get her nipples nice and hard.

“Oh Steph your tits are perfect too. Your boyfriend or husband is the luckiest man in the world.

She said, “Thank you Tony but right now I’m single,” as she started running her hands over the front of my body.

“Oh my,” I said. “Come closer, I need to tell you something.” I whispered in her ear, “I don’t want to get you in trouble here but if you want to be my mistress sneak me your number or email. I have the resources to make you very happy and you can probably stop working here.”

“I’ll think about that Tony,” she whispered as she started to lightly brush her fingers over my raging hard on. “I can’t do this here but I would love to have a cock like this in my pussy sometime. It’s been months.”

“And you have to be around hard cocks all day long,” I said. “You must be out of your mind with lust. Why don’t you get on the bed and play with yourself for me while I watch you and jack off?”

She said, “No one’s ever asked me to do that and I’ve never masturbated in front of a man before. I’m a little embarrassed.”

Steph, “I jack off every day and I’m jacking off for you right now. There’s nothing to be embarrassed about so be my guest, get on the bed and release your tension.”

As she climbed on the bed I got another look at her gorgeous ass and I couldn’t wait to slide my cock between it but I was trying to be patient. I knew I wouldn’t last long once my cock was sliding between her fleshy ass cheeks.

She was on the bed and her hand reached down and started furiously rubbing her clit. Some girls shave all their pubic hair but I prefer it when they are nicely trimmed. Steph had a nice v-shaped patch of brown hair above her pussy. Her pussy was beautiful as well as I could tell her youth by the puffiness. The lips surrounding her pussy were small and I watched in wonder as she played with her clit.

“Fuck Tony, having you watch me play with myself makes me so fucking horny. It’s not going to take me very long to get off.”

“That’s awesome,” I said as I took her left hand and wrapped it around my cock. “Look at my big cock as you play with that pretty little pussy.”

“Mmmmmm, this feels so good and your cock looks so good. Fuck, I’m gonna cum soon already!” I reached out with both hands and rubbed between her thighs then pressed both hands hard over her pussy hair. “Oh yes, mmmmmmmm.”

Her legs tensed and her body shuddered as she leaned forward and off the bed through her orgasm. When she was satiated she said, “That was really nice, now what can I do for you?”

I said, “I have got to feel what your amazing ass feels like so get up and lean over he bed.” She asked me if I wanted oil or baby powder and I never thought to try powder before. In the past all the girls jacked me off with oil but it seemed like the powder would make her amazing ass feel even softer.

“I never thought of trying powder before. Let’s start with that.”

She handed me the bottle of powder and I pumped a generous amount onto her ass and between her crack. My cock was raging s I massaged her ass checks and she said, “That feels nice.”

I placed my cock between her ass cheeks and my ultimate fantasy became reality. Words cannot describe the heavenly feel of her ample ass cheeks as I buried my hard cock between them and the powder made it even better. I had never felt anything so good before or since.

As I started to slide the length of my cock between her cheeks I said, “My God, I am in heaven right now. Your ass feels better than any pussy or mouth I’ve ever fucked before in my life.”

“Fuck my ass Tony. I love how your cock feels, mmmmmm.”

The problem was that after just a few strokes I was getting close to cumming and I still had 20 minutes to go so I pulled back and said breathlessly, “Fuck Steph it feels too good and I’m really close to cumming.”

I added more powder to her ass and back and massaged her while I waited for my cock to settle down. “MMMM that feels so good on my back but I can’t wait to feel your cock sliding between my ass again.”

After a few minutes I placed my cock back between her ass cheeks and slowly slid the length deep into her crack. The sight of my big hard cock sliding up her ass was amazing but after a few strokes my balls tightened up and I almost shot my load so I pulled back again. I said, “I need to try something else Steph, it just feels too good.”

She asked, “What would you like me to do for you Tony?”

“I want to fuck those nice tits of yours now,” I said. We switched positions and I put power on her tits and massaged them as her nipples sprang to life.

“Oh that feels so good Tony,” she said as I knelt on the bed, placed my cock between her tits and she pushed them together and slid them up and down the length of my cock.

“My God this is so amazing,” I said. “Go nice and slow baby or your going to make me cum.” She slowed the pace and I enjoyed the heavenly sensation of her tits as she massaged my cock with them. Her nipples rubbed against my belly causing them to get really hard.

“You have such a nice cock Tony, I love watching it slide between my tits like this.” I was able to enjoy the feeling of her tits for a good ten minutes before I told her I wanted her ass again. “Anything you say Tony,” and she bent over the bed and presented her glorious ass to me again.

I got behind her and this time I was able to slide my dick between her ass cheeks and my orgasm had subsided to the point where I could fuck her ass alternating between long slow strokes and hard fast ones. “Fuck I love the feeling of your ass so much. If you were mine I would do this to you every day after I fucked your pussy to multiple orgasms.”

As I continued fucking her ass she said, “That sounds so good. I can’t imagine what that would be like.”

“I’m an expert at using my cock to get women off multiple times in a row. One time I made my wife cum eight times in a matter of two minutes.”

“God damn she’s a lucky woman to be married to a stud like you. I’d make you fuck me all night long and then pleasure your cock with my ass for as long as you wanted to.”

The picture of fucking her hot young body all night long got to me and my orgasm started to build again. We only had five minutes left so I pulled out and said, “I’m getting close so I want you to jack me off so you can see the huge load of cum I have for you.”

I laid down on the bed and she started stroking my cock and I asked her to lube it with oil so she could go nice and slow. She said, “Whatever you say Tony,” as she grabbed the bottle of oil and put an ample amount on my cock. As she wrapped her hand around my cock and started slowly stroking me she said, “Look at how it glistens in my hand, my God you have such a nice cock.”

“This feels so fucking good on my big cock Steph, mmmmm.”

She said, “I would love to do this all day but we’re almost at time and I don’t want to get in trouble,” so she started jacking my cock off hard and fast.

“Oh yes Steph, just like that. Fuck it feels so fucking good. When I cum make sure you keep jacking me off until I tell you to stop.”

She said, “Of course Tony, I want to make sure you feel really good when I’m done with you.”

“Oh fuck, I’m gonna cum soon. Fuck Steph this feels so fucking amazing I want to spray my load all over your massive fucking tits.”

“Fuck yes Tony, shoot your load all over my big fucking tits so I can massage your cum into them. Give me your fucking cum you big fucking stud,” she said as she bent over and aimed my raging cock at her tits.

“Oh my God yes, Steph, keep doing it just like that, I’m going to cum all over your tits! MMMMMMM!”

She squeezed my tightening balls with one hand and jacked my cock off with the other as I finally allowed my cum to release from my raging cock. The first shot sprayed her tits followed by a second and a third. She cried out, “Oh my God Tony look at your glorious cum! MMMM There’s so much of it.”

As she said that my cum continued to spray her tits and my orgasm became stronger and stronger. Because her mouth was open when she commented on my cum shot one of them found her open mouth.

“Fuck I really shouldn’t do this but I need to taste your cock,” she said as she swallowed my still spasming cock in her mouth and sucked my cock hard as it spewed the rest of my load down her throat.

“Oh my God Steph,” I said during the final throes of my climax. “This feels so fucking good on my cock! Please keep sucking me,” as I grabbed her head and humped my cock deep into her mouth. “Fuck yes, suck meeeeeee! MMMMMMM!”

When I was finally done cumming I laid back on the bed gasping for air as I basked in the afterglow of the most amazing sexual experience of my life.

She said, “My God I just made a huge mistake with you but I couldn’t help myself. Please tell me your free of anything that is going to hurt me.”

When I could finally talk again I said, “You have nothing to worry about Stephanie. My wife and I are absolutely monogamous and your mouth is the only one to taste my cock besides hers in the last 20 years.

“Thank God for that,” she said. “How old are you anyway?”

“I just celebrated my 50th birthday.”

“Unbelievable,” she said. “I would have guessed you were at least ten years younger. Now lets get you cleaned up and on your way, we are out of time stud. She took my cock back in her mouth, sucked the rest of my cum and smiled as she swallowed.

“I still can’t believe I did that,” she said as she grabbed a cloth and cleaned me and herself. “What I great morning this was for me though. I had a nice orgasm and got to suck a wonderful cock and drink your cum too.”

“It was fucking incredible Steph. So what do you think about my proposition?”

“I’m not sure about that just yet Tony. You are married after all but I will give you my email so we can at least stay in touch. No promises though OK? I don’t want to get your hopes up and be disappointed.”

As I got off the bed and started to get dressed I said, “You just made one of my biggest fantasies come to life by letting my put my cock in your ass crack like that so there’s no chance of you disappointing me. If nothing else I can find out when you’re working and maybe next time I’ll fuck that tight little pussy for you. By the way, I want to give you an extra $50 to show my appreciation and next time I want to see you in a new bra OK?”

“That’s so kind of you Tony,” she said as she kissed me on the cheek. “I plan on doing exactly that after work today and maybe I’ll send you a pic.”

“That would be amazing and maybe I’ll send you a pic of my cum shooting all over that pic of you in your new bra.”

“I can’t wait, “she said, “Now you’d better be on your way before I get fired. She kissed me on the cheek and gave my a big hug as she led me out to the door.

“Thanks for a mind blowing time Steph. I hope to see you again soon.”

“Me too Tony, you have a great day now.”

“I think it’s gonna be hard to concentrate when I get to work but there’s nothing that could ruin this day for me babe.”

She giggled as she whispered in my ear, “Take care you fucking stud.”

I smiled and made my way to my car. Luckily I checked my face in the rear view mirror and saw that I had baby powder around my lips. That would have been difficult to explain at work so I wiped it off. There was also some traces on my pants and I was able to clean that off was well. Then I made my way to work with a huge smile on my face.

Author’s note:

99% of this story is true but I embellished the part where Steph gave me her email(SORRY)! If you liked this story let me know where’d you like me to take it next. I have many real life experiences from massage parlors and even a couple escorts that I can share. I could also do some amazing things by shifting to fantasy mode and write about Steph becoming my paid mistress.

Tony Krane

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