Tickling the Boss's Wife

Dorothy Nicholson is married to my uncle's former law partner. After law school, I returned to my home town and worked in Mr. Nicholson's firm.

One day, I took documents to his home, assuming he was there. Mrs. Nicholson greeted me and invited me inside. I had long appreciated Mrs. Nicholson for her beauty and shapeliness. Even as she aged she had not lost her appeal.              

She told me, "Oh, Doug is playing golf this afternoon. Can you leave the documents for him?"

"Yes, I suppose so," I said.

She had been at a women's club event, and was still dressed up a bit in a flowery print dress with jewelry and sensible pumps. And, I might add, looking fabulous for a woman of a certain age.

"Can I get you like some iced tea?" she asked.

"If you don't mind, yes," I said. I settled on a sofa in their den. We sat together and talked a bit. She asked me about college and seemed curious about me. I enjoyed eyeing her long legs and imagining what design of bra she must wear to hold up her large breasts. As we chatted, I sensed that she enjoyed my visit and was almost flirty with me. My cock squirmed, and I tried to adjust it without her noticing.

While she walked, she favored one foot. I asked her about it.

"Oh, just a little tennis injury," she said, "It should go away soon."

"That's too bad," I said, "I worked part time as a trainer for college sports teams. May I take a look at your foot?" Before she could resist, I kneeled on the floor and removed her shoe from that foot and asked, "Tell me what happened?"

I touched and moved her foot, and she didn't feel any pain. "Maybe it's your ankle or calf," I said, as my hands slid up the backside of her lower leg. I squeezed, then began to massage her foot. Pressure on her soft arch made her moan with pleasure. "Just tell me if anything hurts," I said.

"Oh, no, that feels so good," she said. She enjoyed my massage as I squeezed her calf muscles. Then I touched her foot in a way that tickled her. Mrs. Nicholson laughed and jerked her foot away. We both laughed, "I see you're ticklish," I said.

"Very," she replied.

"Well then, I'll have to be sure not to do this," and I tickled her again. She laughed again and squirmed. I ceased tickling and returned to a gentle massage, thinking that tickling her might lead to more fun.

"Let me try something," I said as I squeezed her calf muscle again, then my fingernails teased her leg. Instantly, the tickling sensation made her lose control of her position. Her leg flinched and parted enough to let me see under her dress up above her knees.

I withdrew my hands as she adjusted her dress to cover herself. "Oh, that felt crazy," she said.

"How so?" I asked. "Often can be a fine line between effective massage for injuries and deeper sensations like tickling," I told her. "With your permission, I'll try a bit more."

She nodded, then bit her lower lip. She had slumped slightly on the sofa because of her reaction to being tickled. I sat on a footstool and raised her foot. Her dress slid up to her knee. "Tell me how this feels," I said.

Showing no mercy, I began by gently squeezing her muscles, then tickled lightly. She reacted by trying to escape the tickling. Her legs swayed apart and she shook uncontrollably while laughing uncontrollably. I was prepared for her to tell me to stop, but she didn't.

I rapidly shifted from massage to just tickling her, then back to massage. Just as she relaxed, tickling would make her tense and squirmy while she laughed and gasped for breath. It was a crazed laugh that was on the border of pleasure and a scream. In no time, she was struggling to keep her legs together and her dress down. As I changed from one leg to the other, just up to her knees, she could no longer maintain modesty. Her dress could not stay in place as her legs flinched and jerked from side to side. Soon, she could no longer hide her panties from me.

My touches crept higher. Then I stopped.

"Maybe that's enough," I said.

"She caught her breath and was about to say something, but before she could speak I said, "Nah, I think you like being tickled," and I started all over again. Massage with one hand, tickle with the other. Side to side. First one leg, then the other. Mrs. Nicholson was losing control feeling the panic and pleasure of prolonged tickling, carefully blended with deep tissue massage. Her long legs tried to hide her panties from me, but she just couldn't.

"Blue!" I said. Over her laughter and sometimes gasping for air, I repeated, "I don't often see blue panties." Announcing that I could see her panties had an effect on us both. My cock was bursting, and now she knew that I was looking at her pussy.

She kept squirming to avoid my tickles, but not very hard. Had she objected angrily, I would have stopped, but her efforts to escape were just reactions to being touched in ways that gave her this crazy pleasure.

"You like this, don't you?" I asked. "You don't want me to stop, do you?" My hands were a flurry of tickling and kneading fingers.

"Oh, god, oh god," was all she could say. Her breath was rapid, and the tickling didn't give her time to speak anything but frantic yelps and mad laughter.

Soon her dress was all the way up to her waist, and her long legs were moving from side to side, open and closed, trying to guess where I would tickle her next. My busy hands didn't give her a break, but I was watching to see if she might be in distress. I tried to keep her just on the edge of pleasure while still pushing her toward losing control.

By now, her panties were always in my sight, and I let one hand approach them. She laughed harder and maybe was trying to tell me not to touch her there. I smiled at her and made my first pass over her silky panties, just letting my fingers bounce gently over her pussy so she could feel it but not feel violated. Not yet.

My hands returned over and over to her panties, finding new places to tickler her. Her leg at the panty line was very sensitive. Squirming to escape, her panties crept partly into her pussy crease, with bunches of her hidden hairs now in plain sight. I tickled the skin beneath her pussy hair.

My hands ceased tickling briefly, and with one hand high on each of her legs I pressed into the deep tissue there. She could relax finally and catch her breath as my hands forced her legs wide apart with her pussy covered only partly by her blue panties. "Maybe I should start at your feet and do this all over again," I said to her. Then my thumbs both reached over and massaged her pussy lips through her panties.

Her eyes widened.

"Nah," I said, and instantly I resumed tickling her gently causing her to moan with obvious pleasure, then to shriek with something nearing panic. My hands now rapidly attacked her inner thighs, alternating between one leg, her panty covered pussy, then the other leg. Between her cleft, I felt a hard extended but still hidden clitoris. She had a prominent one that was just right for tickling.

In an instant, my finger would flick her clit while also tickling her outer leg. Then the other hand. The constant attention to her still unseen clit turned her tickle laughs into serious gasps for erotic release. I began slower touches and tickles, managing her through lulls and very short rests. Then returning to fast paced tickles with one hand while the other climbed the hill of her clitoris and camped out on top for a moment.

She was perspiring and heaving, exhausted from being tickled and catching her breath, her necklace flew from side to side. Her large breasts were still fully covered and undisturbed, and I knew her bra had all it could handle to keep her tits their upright and locked position. She was now fighting toward an intense orgasm. She was so worked up that I didn't know if she could be relieved. If an intense climax overcame her, I wondered if I should let her rest or keep tickling her until she begged me to stop?

Just then, she screamed and heaved, her hips bucked as her clit searched for my fingers. I stopped tickling and took her clit bud, still covered by her blue silk panties, between my thumb and forefinger. I squeezed it gently with one hand while tapping its tip with my other fingers. She had climaxed but each tap produced a gasp and a bit more release.

Finally, she exhaled deeply and opened her eyes.

Still holding her clit between my fingers, I asked, "Feeling better?"

Mrs. Nicholson let her head fall back, breathing deeply, and offering no resistance. I stood and unbuckled my trousers. She didn't bother to watch as I undressed. Her eyes were staring at the ceiling in a blank gaze as my hard cock got ready to finish the job.

But first, I spread legs wide and pulled down her blue panties. Her enlarged clit was flanked by puffy lips and folds of her pussy. When she felt my tongue touch her, Mrs. Nicholson relaxed and spread wide. Just three or four laps with my tongue had her back on the edge of another climax. In less than a minute she was over the top again and beyond ready to be fucked.

As I aimed my cock at his wife's pussy, I hoped that Mr. Nicholson was still on the back nine holes as I entered his wife's hole. She hadn't seen what was sliding slowly into her, but from her reaction I guessed my dick was more than a match for her husband's dick.

I remembered Benjamin Frankin's advice to young men that it is best to learn sex from older women because they are more experienced, won't get pregnant, and are grateful for the attention. As my cock entered Mrs. Nicholson's pussy, I thought that old Ben was right.

I figured that Mrs. Nicholson had had enough for one day, so I didn't prolong the penetration. As I fucked her, I seemed that her orgasms continued but in a gently diminishing way, each additional one relaxing her until my own climax left her in a puddle of pleasure and cum.

It took a while for us to find our feet and begin to talk again. We dressed and were decent again just in time for Mr. Nicholson to come home.

"Hi, honey," he called out.

"In here, dear," she called back.

He entered the room and saw me and said, "Oh yes, you brought the documents?"

"Yes, sir," I replied, "I hope I delivered satisfactorily."

His wife smiled at me and said, "He sure did."

I turned to Mrs. Nicholson, "Let me know if you need more treatment."

She looked at her husband, "He helped me with my tennis injury."

My boss said, "That was nice of him."

She said, "Yes, I think more treatment would be very nice."

I smiled at Mr. Nicholson and said, "If my boss gives me time off to come back, I'll be glad to give you more treatment." Thinking of her breasts, I added, "There are some parts we didn't get to."