Undercover Rose 90 (Edited)

By Cindy and Walt

After the late lunch we drove to the motel.  Once the door was closed Jeff began kissing me.  I wasn’t less excited since I knew he was gay, I was actually more excited.  I kissed him deep and long. 

My hands wandered over his body, as his did over mine.  Since I wore the elastic bandage I could feel nothing through my nipples.  It was fine since Jeff did not attempt to stimulate me through my breasts.

He rubbed my ass a bit through my jeans then slipped his hand inside.  He slipped his hand right down to my rectum and began to gently massage the rear opening to my body.  At first it was mildly uncomfortable, but I grew to accept it.  Then I began to find it erotic.

He obviously understood the reaction I was having to his ministrations, because when I gasped, he stopped then quickly penetrated my sphincter.  I felt the stretch but not the pain of penetration usually accompanying such an action.  The feeling of fullness wasn’t all that unpleasant or uncomfortable.  I quickly adjusted to the feeling of his finger inside me. 

I found myself pushing my ass against his hand without even realizing it.  I had to break the kiss just to breathe. 

“I have something for that beautiful mouth hon,” he whispered in my ear.  I gasped again.  “You old guys love to suck a young hard dick.”

“Yes,” I groaned.  It was all I could manage and he knew it.  I found my hand wrapped around his exposed penis, but I couldn’t remember putting my hand there.  I also didn’t know if I had removed it from his jeans or not.  All I knew is that I was desperate to suck on it.

He was holding me up and I was whining to be released.  When he did I fell to my knees and took his hard cock into my mouth.  He was young and his erection was very strong, but his ability to control his orgasm was weak.  It took only second for him to cum in my mouth.  I didn’t even have time to work his cock down my throat.  My mouth was just full of hot thick cum without any warning.

I stood to kiss him with a mouth full of his cum.  He shuddered as he sucked his own cum from my mouth.  It was a highly erotic moment.  He quickly stripped me naked and pulled me to the bed.  He arranged me to lie beside him, but with my face only inches from his wilted cock.  If he thought that would excite me he was correct.  From time to time I took his cock in my mouth to feel his strength.

“Get dressed,” he said.  “We are going to dinner.”

I dressed quickly and without a word.  He helped me arrange the bandage on my chest.  Once I had my panties on he kept his hand on my ass.  I removed it only when I pulled my jeans on.  Then it was right back there massaging and rubbing me.  He had all the nerve ending in that area screaming for attention for his hard young cock.  Instead of helping me he almost forced me out the door of the motel and into the car so he could take me to dinner. 

I began to silently beg him to fuck me as we drove to the restaurant.  Then during dinner I could think of nothing else.  After dinner he asked, “Would you like to go to a club?”

“No,” I replied.  “I want to go home to feel your hard young cock in my ass.”  I had never felt so blatant or so desperate.  When we finally got back to the motel I almost forced Jeff to get on with it.

He had me naked within seconds of entering the room.  Then he had me on my hands and knees on the bed.  First I sucked his cock till it was hard, then he turned me so that my ass was presented to him.  He lubricated my anus with a combination of my spittle and his precum.  His penis wasn’t large so the only discomfort I had was the slight sensation of fullness I associated with the need to empty my bowels.  That discomfort did not stop me from begging for his cock.  I felt him begin to stroke me gently at first then more rapidly and deeper.  He was working toward his own orgasm with no regard to me.  I was almost ready to reach down for my clit to finish my climb to an orgasm when I suddenly exploded into an orgasm from the feel of his cock in me alone.  I had done it before, but it had always been less than comfortable.  Taking Jeff’s cock up my ass felt wonderful from start to finish.  When he finished emptying his semen into my ass, he immediately went into the shower.

I just lay on the bed enjoying the feeling of his sperm seeping out of my ass.  I was enjoying the sensation when he stood in the bathroom door and said, “Baby you have got the best ass pussy I ever had.” 

“Why don’t you come here baby and suck my tiny cock,” I said to him.

He came to the bed, forced me to spread my legs, then wedged his face against my clit.  He stopped, raised his head, then said, “Tell me to suck your cock again.”

I complied several times begging him to suck me.  I rewarded his efforts with huge orgasms.  I did it several times before he grew tired and stopped.  He rolled onto his back and stopped me from climbing on top to ride him.  Instead he moved me down to suck his cock again.  I did it gladly.

He couldn’t cum again, but we both enjoyed the sensation.  Finally he stood and dressed.  “Do you really have to go,” I asked.

“We don’t want Simon worrying do we?” he asked.

“We don’t give a shit,” I said reaching for him. 

He slipped though my fingers then said, “You have a great ass pussy, but I do have to get home.”  He said it being much colder than I ever remembered him being before.  It really was okay because my leg had begun to hurt.  It was funny that it hadn’t hurt the whole time we were making love, but started as soon as we stopped.

I took a couple of the strong pills I save for the really hard pain.  Fifteen minutes later I managed a shower.  I paid special attention to my rear.  I didn’t have even a small bag I could have used to wash the track, so I just tried to force a wash cloth up there.  It actually felt kind of erotic, but it wouldn’t go in very far of course.  I knew for a fact that I was going to have seepage all day.

I had laid around nursing my various pains until 7 AM.  After the long hot shower I struggled to the truck using the cane.  I had arrived for breakfast at close to 8 AM.  I found a table by the window when I set my tray down.  The customer base had changed in that amount of time.  Instead of the parking lot being filled with work trucks there were screaming kids everywhere, mostly moms with kids on the way to the soccer fields.  It made breakfast less than a pleasant experience for me. 

“It’s just breakfast,” Liam said.  “And you have had worse.”

“Yes I know there were mornings my ass hurt so bad it was hard to sit still.  One or two of them were even sex related,” I joked.  “So what’s our plan for today.”  I noticed a kid in the next booth staring at me.  I smiled at him as pleasantly as possible under the circumstances.

“I think you need to get a gallon of coffee and go to your room and think about Bart’s offer,” Liam said.

“You know I built that business from nothing,” I said into my powered down cell phone.  I used it so people wouldn’t move away in fear.  I didn’t mind them moving away, but someone would use their cell to call the psych cops and then I would have to explain.  It was easier to pretend to be on the phone.

“Come on old girl the challenge is gone.  It’s just a job now.  Hell you can’t even blame it on the leg.  You are getting around almost as good as before,” he said.

“Hey, I know Bart did as much to start the thing as I did, but I hate to start over.  I really do,” I said.

“Or do you hate to start over without Bart.  You can’t lose what you never had, old girl.”

“Liam shut the fuck up,” I said putting the phone away.

Back in the motel I read my email and tried to decide what to do.  I checked my files to see if I saved Sam’s daughter’s new address and found I did not.  Since the County was having an auction, I didn’t need to contact her.  However if I did I might be able to short circuit the auction.

I knew those auctions could be a bargain hunter’s dream but just as often they turned into a nightmare.  If I could buy it for a thousand dollars, plus pay off the ten grand lien it would probably still be a good deal.  There were only a few acres of land and the few half ass work buildings left.  There were also the catfish ponds to deal with.  I sure as hell didn’t want to do that.

I called Miss Sadie.  “Miss Sadie it’s me Iris Martin.  I need a favor.”

“Sure Iris anything.  We are all family here,” she said.  It would also be a chance for her to gain some juicy gossip, which was probably motive enough.

“Do you know where Sam’s daughter and new husband have gone?” I asked.

I have a cell phone number for her.  I have no idea what has happened to them.  Let me just find my book and I’ll give it to you.”

I waited and wondered what I was really going to do.  I knew that I was going to get all the information I could, only then would I make a decision.

“I’m going to email you Lisa’s new number,” Miss Sadie said showing me she was the master of the new technology.  I didn’t tell her how old the technology was.

Several minutes later I was on the phone talking to Lisa.  “So how have you been hon?” I asked.

“I’m fine.  Robert is managing five restaurants for a franchise owner from the Middle East somewhere.  It’s a pretty good job,” Lisa said proudly.

“That’s good honey.  I called to ask you if you knew the County Clerk was planning an auction of your dad’s farm soon?” I asked.  The Sheriff’s auction was just what it was called there were no more Sheriffs but the auction was still called a Sheriff’s Auction.

“Yes I don’t want any part of it,” she said.

Then if I send you a contract to sign the deed over to me for a hundred dollars and I agree to assume the tax lien on the place would you do it?”

The tax lien isn’t the only one.  There is a five thousand dollar bank lien as well but if you want sure I’ll sign it over.  You can forget the money.  Robert and I owe you so much more.”

“That’s enough over the phone.  Give me your address and I’ll mail you the contract.”  I knew Rita would handle the purchase, if it meant getting rid of me.  I decided to buy the farm regardless of anything else.  I still had time to think about the Irish Tea business after I owned the farm.  I put a call into the County Clerk at home.  Rural counties still did business from home for a prominent business person.  I explained to her that I was in the process of buying Sam’s farm from the daughter.  If she agreed to hold off thirty days I would have the lien settled in full.

“That piece of property comes up for auction in two weeks, but if you are serious we can slip it back to the next month.  That will give you six weeks,” she said.  ‘You are going to have to have a lawyer call the office to verify all this.  Now I really have to go.

“I have a verbal agreement and I will have the lawyer send a letter of intent no later than Tuesday.”  I had the two weeks to get it done.  The County wanted their money and not to have an auction.  They might get less in a public auction.

I wanted to settle the farm things that same day, but of course that was impossible.  What was possible was to go to a department store and buy some new clothes.  Even though I wore girlie clothes, they weren’t exactly right for trying to look like a gay man dressing girlie.  I know it just sounded fucked up to me as well.  Nonetheless I went out and bought shirts that make me look like a man trying to look like a girl kind of.  I laughed inside every time I thought of it.

Since it was just a couple of days of pretend I didn’t spend all that much money.  The skinny jeans on my skinny ass were fine.  What I did buy was a three pack of men’s undershirts and boxer shorts.  Then I bought a very masculine cut over shirt but it was made from a fabric with a loud print.  I thought it might make me look even more gay.  Then I bought a blue work shirt in the smallest size they made for my macho look while driving home on Sunday.  It was a really hilariously stupid idea.

I had dinner alone dressed in my gay outfit then went to meet the ‘boys’ at Rosie’s Restaurant and Bar.  We were meeting in the bar area.  I parked the truck in the restaurant’s parking lot.  I was surprised by how many other pickup trucks there were.  I wondered if there were that many openly gay men driving pickups, or were there that many in the closet pipe fitters.  It should be interesting, I thought.

Inside the Bar and Grill the meeting was for an after dinner drink.  The two men spent the afternoon together, but agreed to meet with me at Rosie’s.  I spotted them at a booth for six.  I guessed from the seating arrangements they were expecting others.  Well it should be interesting to say the least.

“Well hello Jeff,” I said as I entered the booth.  “This must be Simon.  Jeff speaks very highly of you.”

“He speaks highly of you as well,” I saw Simon checking out the neck warmer I wore.  It was very fashionable but not so much functional.  He was checking me for an Adam’s apple.  I didn’t wear the neck warmer to make a fashion statement, but to hide the fact that I didn’t have an Adams apple.  I knew some men looked for the sign of one to distinguish a transsexual hooker from a real female one.

In my old business, the cover was everything.  I was again happy that I knew how to maintain a cover.  It was the attention to details that kept one alive when undercover.  I knew that before I ever went under cover.  I don’t know how I knew, I just did.  I must have had him at least guessing, since he never really asked me what sex I was.  Jeff hadn’t told him anything except I was visiting from out of town to work in the lab a few days.

The conversation at the table was lively as I tried to make a good first impression.  It didn’t take long before we were joined by a married heterosexual couple.  It was also their first time at Rosie’s.  The three of us compared notes while the men, Jeff and Simon, watched.

“Shall we play guess the fag,” I suggested.

“It won’t be hard almost everyone here is,” Simon commented. 

“Now don’t be bitchy Simone,” I said with a giggle.

“So how big is your clit,” Simon asked.

“Why 13 inches of course.  But if you want to measure we can go to the little boys room,” I replied.  “There might be a little boy or two hanging around.”

“Oh no, I believe that you are exaggerating,” Simon said

“I’ll be happy to show you, if you change your mind.  How about you Trudy would you like to see?” I asked the women of the married couple seated with us.” 

“Well I have never seen one that big.  I mean I have seen one in a movie, but not in real life,” she said. 

“Then come with me to the boys room,” I said.

We stood to walk into the men’s room hand in hand.  I pushed the jeans down and showed her the bulge in the men’s boxer shorts.  “Any more and you are going to have to kiss it,” I demanded.

“In that case I have seen enough,” she replied. 

“That’s good because I do kiss and tell,” I said with a laugh, one in which Trudy joined me.

When we returned from the bathroom, Trudy was ready to swear I had a huge cock inside my jeans.

She blushed when I said, “She looked but she wouldn’t touch it.  Shame really.”

“Maybe for you,” her drunken husband suggested.

“Yes, I’m sure since she has a purdy mouth,” I said.  “After all we are in Georgia.”

Everyone laughed except Trudy’s husband.  “I’m sorry man.  I didn’t mean to embarrass you.  I was just pulling Trudy’s leg a little.  I don’t suppose you would be interested?” I asked her husband.

“Hardly, I find you crude and just plain gross,” he said.

When I left the table on the way to the bathroom, Simon followed me into the bathroom.  I figured he would call me on being a fake, but instead he pushed my face against the wall and held me there with one hand.  He unbuttoned and pulled down my jeans and boxers with the other.  He was too busy working on his own clothes to notice I wore a belt around my naked waste.  The belt had a folded part of socks taped to it.

Simon shoved his dry cock into my ass and pumped away.  He came quickly as another man watched.  From the moment I felt his cock in me I rocked back against him.  “Fuck me,” I whimpered.

“Say please bitch,” Simon said.

“Please fuck me hard,” I begged.  Simon did just that and came within three minutes.  He left me stand still face pressed against the wall.  “You want some of this?” he asked the man standing and looking.  I turned my head to see him shake his head and walk away.  “Put on your fucking pants before they miss us,” he said, his anger showing in his voice.  He left me standing there alone and returned to the table as if nothing had happened.

I dressed.  I also remembered to wash my face before I left.  When I returned to the table, I sat across from Simon and finished my drink.  “I know Jeff fucked you,” he said to me.  “So now we both have.  How about you two do you want to fuck this whore.”

“I’m not into doing it with guys,” the husband said.  I acted as if I wasn’t there.  Jeff looked at me and smiled while Simon tried to pass me around.  Fortunately no one took him up on it 

I sat quietly through the rest of the evening.  Trudy whispered to come to the men’s room with her.  I shook my head and stayed put.  When the night ended, I expected to go home with the boys but Simon said.  “No way Jeffery, he is a slut.” and stormed off. 

“Sorry Iris,” he whispered.  Then he went to join Simon in their car.  I drove back to the motel alone.

So I had been a gay man for an evening.  To bad I didn’t like it at all.  I might do it again someday, but it would not be anytime soon.  I knew that I was sexually perverse to the point of being a bit of a pervert myself.

Sunday I got out of bed early and staggered around the parking lot for fifteen minutes then loaded and drove the truck to breakfast.  I wasn’t upset at all about what happened at Rosie’s.  It was a learning experience as it should have been.  I looked at the black woman behind the counter.  Too bad I’m leaving she looked interesting, I thought to myself.

I had a not so great weekend but you know that’s how life is.  As they used to say at Church Camp sometimes you eat the bear and sometimes the bear eats you.  So I didn’t feel all that bad, since I only got eaten a little, and it only hurt a little.

I drove home positive I would be returning to my online lover.  The Dark Daddy was the only one on my radar for the time being.  I was even looking forward to the banter as well as the sexual word play.  I had plenty of sex for a while so I needed to get the business of the pot farm settled.

I got home around dark, which seemed earlier every night.  I knew that the weather was going to change some, but it stayed warm a long time in Alabama.  Even when it was supposed to be cold, it wasn’t all that cold.

I walked into the studio wearing only a tight fitting tee shirt and jeans.  They were covered by a hoodie jersey jacket.  I hoped Bart didn’t decide to shoot me, since he really wasn’t sure when to expect me home.  I also knew that Rita planned to come to town, but I wasn‘t sure whether she was staying in the studio or a motel in Williamston.  Frankly I was hoping for the motel. 

Those hopes were dashed when I had seen her car parked in front of the studio.  It was barely 7 PM, so I expected them to be out of bed and sitting all night and romancing upstairs in my room.  Actually they were in my room.  I had hoped they would at least be out to dinner when I arrived, but there they were sitting in front of an obviously new flat screen TV.  They cuddled together watching a show from the Internet.  The TV was new, but Bart had the advanced computer since early on.  He had bought it to entertain himself.  Probably watching porn, I thought.

“I like your TV, but why do you have it in my studio?” I asked.

“Sorry Rose, but it wasn’t a good fit going up the stairs with just Buddy to carry it.  We will move it out, if it comes to that.”  Rita obviously didn’t plan to be the one discussing the business changes.  She had probably made a good decision, since I hadn’t stabbed anyone in over a year.


About cindypress

sorry it is a mystery.
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8 Responses to Undercover Rose 90 (Edited)

  1. jackballs57 says:

    Ah , life’s little diversions that that we do from time to time., Stay warm it’s cold here. Thanks

  2. oldsilvertip says:

    in the closet pipe fitters. This one really made me laugh out loud.
    Currently -10F, but at least the 25mph winds have stopped. 6 ft drifts in the yard. When my son came by to plow this morning at 4am he said there was a 7 footer outside the gate that he had to go through to get to the gate. He went ahead and plowed out the street also. Pretty cool of him. Let’s hear it for Fisher wood stoves.

    • cindypress says:

      Speaking from one who had her gas boiler out for four days over a cold winter weekend, I would loved to have had my mother’s old wood cook stove that weekend. The heat from a ceramic electric heater is just barely better than a campfire in the middle of the livingroom floor. In other words I second the hooray for a wood stove.


  3. KO says:

    Well on the birght side, if there is one, at least Rose was able to get laid and get her rocks off a couple of times before being left high and dry. Simon/Simone is VERY fortunate that Rose has that sumissive side or he may never have returned to the table . . . . after Rose stuck a Porter stake in his throat or heart that is. 😉
    Sounds like the “Tea” business is going to be a changin’ for Rose in the very near future also!
    Thanks for the great read!!
    BTW, we dodged the bullet here over the weekend. Lots of rain and in the high 40’s in the valley, but PLENTY of snow in the mountains. right where it should be!! 😀 Hope that all-ya-all have warmed up considerably by now! That is miserably cold weather!!

  4. YW says:

    New fan of the series.. Keep this going! When’s Rose getting her implants back? 🙂

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