The Stud Gets A Butt Plug

The cougar treats the young maintenance man to a really deep massage.

This is the third part of the story. You can read the earlier parts: The Plumber Cums and Cougar Gets Spanked

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A week after spanking Helen, I was driving the maintenance cart to a job when my phone rang.

I tapped the answer button, and said, “Good morning, how can I help you?”

“Is this Mr. Courtland?”

“Yes.” I recognized Helen’s sultry, teasing voice. I knew she was up to some role playing game. My cock twitched with anticipation.

“This is Helen with Miracle Massage. I want to confirm your appointment for tomorrow at twelve-thirty.”

I smiled, wondering what game she had in mind. “Yes, of course, I’ll be there.”

“Wonderful! See you then. Good-bye.”

At lunchtime the following day, I parked beside her building. I glanced around and saw the blinds on Helen’s front window slowly close. She had been waiting for me, and saw me arrive. I paused, allowing a woman walking her dog to pass out of sight, and then I walked quickly to Helen’s door. I knocked lightly.

“Come in,” Helen called in a cheerful voice. “Ah, Mr. Coutland, right on time,” she added, as I entered the apartment.

I smiled, looking at the arrangement in the living room. The furniture had been pushed back and portable massage table had been positioned in the center of the room. Helen was dressed in a white nurse’s scrubs. Her hair was pulled back in a ponytail.

“So,” she said, referring to a clipboard, “this is your first visit with us.”

“Yes.” I had never been to a massage parlor. Doubtless the majority of the establishments were strictly legitimate services; however, I’d heard many stories about the ones which catered to men and offered a happy ending to the massage. I was certain this was the adventure Helen had planned for me.

“Well, if you will begin by getting undressed, and then lie on the table.”

“All of it?” I asked, motioning my hand over my torso.

“Whatever makes you comfortable.” She picked up a folded towel and unfolded it. She cocked an eyebrow as she draped it over the massage table. She discreetly turned her back and began sorting items on a small table.

I hastily stripped-down to my undershorts and climbed onto the table. I positioned the towel over my bottom.

She turned around. “Ah, I see you are ready.”

“Hmm,” I mused, with my face positioned in the hole in the table.

She squired some lotion into the palm of her hand and began to massage my shoulders. It felt really good, and I decided I would have to try a for-real massage parlor someday. She worked her way along my right arm to my hand. She massaged my palm and each finger. She worked slowly, and I wondered when, or if, she was going to get to the sex part. I had an afternoon appointment and had not expected to spend all day playing with Helen. She repeated the process with my left arm, and then shifted her focus to my lower back.

“Oh, my, Mr. Courtland, you are so tense. I can see why you booked this appointment.”

I groaned as her thumbs bore into my muscles; I wondered if she had any medical training along these lines. She edged lower, inching her fingers under the towel. She discovered the waistband of my underwear and retreated. And then, she shifted to my upper thighs, bypassing the towel and my buttocks. Moments later, her fingers were once again under the towel. She edged the tip of a finger under the elastic leg-hole.

“We don’t really need these, do we?”

Before I could answer, she reached all the way under the towel, gripped the waistband, and pulled my undershorts down to my ankles. With another tug, she whipped them off and tossed them onto the floor.

“There, Mr. Courtland, isn’t that so much more comfortable?” She replaced the towel over my bare bottom. When I didn’t answer, she added, “Eh?” and rested a warm hand on my right butt cheek.

“Yes,” I said.

She continued massaging my right leg all the way down to my foot. When she reached my foot, she gave it the same treatment as my hand. That is, she massaged the palm of my foot and each toe individually. She switched to my left foot, and worked her way up the leg. When her massaging fingers returned to the towel, the occasionally slipped a bit too high and brushed across my scrotum. After doing it the first time, possibly by accident, she did it several more times until she accidentally touch my cock.

I was hard.

She touched my member again. This time, her fingers lingered. “Oh, my, Mr. Courtland. I see you have even more tension than I anticipated. Perhaps, you could benefit from some of our, uh, deeper techniques. Would you care to try it?”

Now, I knew we were into the fun part of the game. “Sure.”

She turned away. With my face in the massage table’s hole, I couldn’t see what she was doing. My swollen cock was uncomfortable in the downward pointing position, so I took the opportunity to shift it up and pin it between my belly and the table. She returned her attention to me. Her fingers graced my bottom. She massaged my butt through the towel for a few seconds, and then pulled it off to continue massaging my bare butt with one hand, while her other hand reached under my body to hold my erect member. She wasn’t caressing my cock directly, so this was not likely to spur me to orgasm. I waited for something more.

Suddenly, she parted my cheeks and placed something cold against my most private spot. Reflexively, I rose up and turned. She placed a firm hand on my back, pressing down.

“Easy, tiger, nothing to worry about. I think you need a deep prostate massage and there is a little matter of pre-cleaning.” She held a white wipe in her hand.

As she resumed her task, I laid back down.

“There, there, that wasn’t so bad, was it?”

I didn’t answer as she immediately initiated massaging my balls and the space leading up to my anus.

“You are still very tense. I sense you need the full treatment. Just hold still, this might be a bit uncomfortable, at first, but don’t fight it.”

She dripped something cold along my crack. I turned to watch as she held a stainless steel butt plug in one hand, and a tube of lube in the other. She spotted me looking and smiled.

“Now, now, Mr. Courtland, this is for your own good. You will feel so much better once we get all that tension out of you.” She lubed up the butt plug, and I grimaced as she gently inserted it. “Now,” she said, patting my bare bottom, “how does that feel?”

“Uh, uh, full. It’s a pressure from inside.”

“Hmm, yes.”

She resumed firmly massaging my bottom, and then shifted to a gentle caress of my balls and cock. I had softened during the insertion procedure, but she quickly had me rock hard once again. Lying on my belly had become quite uncomfortable.

“Why don’t you roll over now, Mr. Courtland. We’ll finish off by removing the rest of the tension.”

Helen backed away and I rolled over. I was somewhat proud of the way my member straightened and pointed to the ceiling. She slipped off the smock to reveal her bare breasts. She place my right hand on her tit. I caressed her taut nipple.

She smiled and hummed quietly as she wrapped her hands around my shaft. After applying more lube, she got seriously interested. One hand cupped by butt and her fingers moved the plug around in small circles while the other stroked my shaft and glans. I slipped my hand down from her breast to the waistband of her scrubs. Inside, I discovered she was not wearing panties, and was shaved bare. As she stroked my cock, I caressed her clit.

“Be a good boy. Come for mother,” she said, as the frequency of her strokes increased. “Come for me now.”

In a moment, I did as she asked. Lying on my back, I could see the rope of white cream jetting a foot into the air as I came.

“Ah, yes, such a good boy, Mr. Courtland. Mother’s real proud of you.”

I relaxed and she continued her gentle caressing until I was soft. Then, she used a damp cloth to clean things up. She kissed me.

“Now, Mr. Courtland, don’t you feel oh so much better.”

“I do, I really do.”

“Good, now it’s my turn.” She dropped her pants and climbed on the table. She positioned her slit over my mouth. “Be a good boy. Do a good job for mother, hmm,” she said, as my tongue slipped inside her.

I was immediately concerned that the folding table would collapse under our combined weight, or perhaps tip over with the unbalanced load. But, I pushed these ideas aside. Sitting on my face was one of Helen’s favorite things to do and I knew just what she liked. I got to work pleasuring her.

After I finished her off, she helped me off the table and dressed me as though I was a child.

“Until next time,” she said. Still nude, she escorted me out the door. “Tell me, Rocky, have you ever done anal?” she asked, standing nude in the open doorway.

“No.” I swallowed, anticipating what she would say. “Have you?”

She shook her head. “Maybe we should try that next.” I nodded. Her lips parted as though she was going to say more. After a pause, she added, “Maybe we should try pegging too.”

“Pegging, what’s that?”

Helen smiled. “I think you’ll like it.”

It wasn’t until I sat in my car that I realized the butt plug was still in place.

THE END

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