One Night With The Chaperone

By the spring of my senior year of high school in the early ‘80s, nothing had clicked with the girls.  Even though I turned 18 in February, I was still an awkward virgin.  I was wildly attracted to girls at school, but just couldn’t seem to figure out how to approach them.  I also had a platonic friend who I lusted after so badly in middle school, but who was now a close friend-and nothing more. Throughout middle school and high school, I had spent hours at her house, gotten to know her family, but nothing had ever happened.  Her father was aloof, a high-powered executive with some defense contractor.  Her mother, “Mrs. O”, was always nice to me.  I didn’t pay much attention to her, but in hindsight, she was attractive, a smiley brunette with shoulder length hair and a nice figure. She also had remarkable bubble butt.  Not wide or overly large-it just protruded prominently. I think I saw her once in a swimsuit.

Flash forward four years to my senior band trip.  Mrs. O was a chaperone.  All the students-there were about 40 of us-were paired up by rooms.  We were staying in just-vacated dorm at the state university.  The parent chaperones, and the teacher, each had their own rooms.  Away from home with our friends and minimal supervision, we would run amock until all hours of the night during the three nights we were there, the chaperones trying to get us into the correct rooms, policing us, and generally trying to get us to settle down.

Late in the evening on night three, I had just left a room and was heading to the communal bathroom to pee when I passed Mrs. O’s room.  Her door was open, and she was trying to hang something inside the armoire.  She glanced up as I walked by.  “Can I help you” I asked?

She said “thank you! The rod inside the closet fell off, and I’m trying to get it into bracket.”  I walked into her room, squeezed in next to her, and was able to easily lift the rod back up into the u-bracket.  As I turned to leave, I realized for the first time how much taller I was than her.  She looked at me.  I caught a smell in the air, and could swear she’d been drinking.  “Stay and talk with me a minute.  We haven’t talked for a long time.”  So I turned one of the desk chairs so that it faced the center of the dorm room and sat down.  Mrs. O was still standing by the armoire near the door.  She spent the next 10 minutes or so asking me about classes, my plans after graduation, whether I was going to stick with music.  But it didn’t really seem like she was listening to my answers.  Instead, she kept looking at me intently.

“I was just getting ready to get in bed when you came along.” She was wearing a robe, but clearly had a some type of black garment on underneath it. She suddenly reached over and closed the door and latched it.  “We can’t have people seeing you in here.  They might get the wrong idea!” I remember how the words shocked me.  Wrong idea? I mean, this was Mrs. O!  In hindsight, she was probably around forty, which was inconceivably old.

She turned, took off the robe, and hung it in the armoire. She was wearing a black nightgown that reached her knees.  I remember being startled because while the bottom seemed to be made of a satin material, the back was almost sheer.  I could easily see her naked back. Without even considering it, I could feel my penis abruptly stir in my gym shorts. What was going on?

As she turned back around, she was still talking “I always liked you best.  I wish Jennifer would have gone with you, but I’m glad you’re still friends.”  When she had turned around to face me, I realized that the front top of the nightgown, while covered with an embroidered-like pattern, was still essentially made of the same sheer material.  I could clearly see Mrs. O’s breasts and nipples as she stood there.

“Do you have a girlfriend now Robbie?”

“No, no.” I stammered. “no, I don’t”

“Is there anyone special out there that you like? Her head was tilted downward, and she was looking directly at me.  I was fully erect.  I shifted in the chair, tugging at my tee shirt to try and conceal my raging hardon.

I shook my head.  I couldn’t think of anything to say.

She tilted her head to one side, and continued to look at me intently.  “Do you like looking at my body?”

I was embarrassed, and shocked.  But I nodded.  She raised both hands, then traced her fingers over her nipples.  I could see them visibly stiffen, pressing against the mesh.  I was mesmerized.  She slipped one of the shoulder straps down-her right one, so it was loose on her upper arm.  The top slipped down, exposing a hit of her areola; but she brought her right arm in, cradling that boob and the barely-covering top in the crook of her elbow while her hand rested on the front of her other boob, momentarily covering her that nipple. She then stepped toward the door and switched off the overhead lights.  The room was still bathed in the warm light from a pair of lamps, but the harsh overhead fluorescent lights were off.

She turned and faced me again, now letting her elbow slide down, exposing more of the areola and her nipple, while at the same cradling her boob a bit, so it was lifted.  It was now fully exposed as she stared at me.

“Do you like this?”  she asked. I nodded in response. She then slipped her right hand up, slipping the left should strap down.  I watched as more and more of her other boob was exposed. I was in shock. Mrs. O’s entire right boob was exposed, and only a scant amount of nightgown covered her left boob.  I could have sworn I was starting to see her left nipple starting to peek over the fabric. I was acutely conscious of the fact that she appeared entirely naked from mid-chest up.  I was almost embarrassed to be staring, but didn’t want to look away.

“Show it to me” she said.

“What?” I was momentarily taken aback.

“Show it to me” she said again.  “I want to see what’s in your pants.”

It was like I was in a dream.  I slowly slid my shorts and white briefs down to my thighs. It was a little uncomfortable, since my legs were trapped in the briefs.  My boner was still hidden under the t-shirt.

“You can take them all the way off” Mrs. O said, gesturing with one hand at my shorts. I dutifully slid them to the ground in a pile, and was left sitting in my t-shirt.

“You can take your shirt off.”  I did, and was left sitting naked on the chair. I wasn’t sure what to do. “Relax” she said. “You can lean back.”  Now my jutting penis stuck up as I sat in the chair.  What was she going to do next? She gazed down.  “That’s a nice one” she murmured.  I couldn’t think of a response.  There were a few moments of silence.

Then Mrs. O took a few steps toward me, letting the top of the nightgown slide down to the bottom of her ribcage.  She was only standing about two feet away, her fully exposed boobs at my eye level.  I was mesmerized.  They were larger than I thought, with half-dollar sized pink areolas, taunt and tight. Her nipples were hard, jutting out like small thimbles. I gaped, unsure of what to do next.

Reaching down with one hand, she lifted my right hand, placing it on the swell of her breast. I squeezed slightly, marveling at the softness, the way it yielded. I slid my hand up cradling the outside curve.  I momentarily forgot my erection as I slowly moved my hand upward.  For some reason, I decided I should avoid the nipple area with my hand. After a few up-and-downs, Mrs. O grabbed my fingers, and guided my hand to the center of her boob.  I could feel the hard nipple as my fingers rippled over it.  Then she held my hand there, gently working my fingers against her nipple.  I heard her exhale deeply.  After a few moments of me feeling her boob, she dropped my hand away and stepped back.

At that point, I didn’t know what I should. She looked over her shoulder, then grabbed a chair so it was facing mine- and slid it up so it was only a few feet away.  Then she primly sat in the chair facing me. She reached down and pulled up the hem of the nightgown, first exposing her entire thighs, then wriggling a bit so the nightgown was pulled all the way up to her waist.  I could see a thick patch of dark pubic hair emerging upward from between her thighs- the only thing left covered by the nightgown was her stomach, her breasts still exposed.  Then she carefully put one foot on the front of each of chair arms on my chair.

I was looking at an essentially naked woman, just a few feet away. I looked down and could clearly see the pink lips of her pussy and the cleft between them, standing out from her pubic hair. I could feel myself twitching.  I desperately wanted to do something, anything.  But before I could decide, she reached between her legs while I watched. She looked straight at me while her fingers began stroking those pussy lips, running up and down them.  I could have sworn I saw the opening get larger.  The lips began to glisten, and Mrs. O buried her fingers near the top of the opening, gently working in a circular pattern.  I think what struck me was how gentle and small the movements were.  When I jerked off, it was a lot of motion, almost a violent tugging.

But as she work those fingers, I noticed a red blotchiness begin to appear on her chest above the larger part of her boobs.  I couldn’t stand it and felt for my own hard penis, I squeezed the head, and felt the wetness from my precum oozing out.

“Touch yourself for me.” Mrs O’s voice was husky.  I slowly began stroking my erection, sliding my hand up and down.  I kept watching her, looking from her wet pussy to her hard nipples and flushed chest.  I could hear her breathing going ragged.  I began stroking faster and harder.  This went on for a few minutes.  I began grunting as I could feel my own cum getting close.

“Stop!” Mrs. O said. “Don’t finish.”  I let go of my erection, which felt like it was pulsing.  I was so close.  She began rubbing faster while I watched.  Abruptly she exhaled with a groan and her body gave a few rhythmic shudders.  Her eyes were closed now.  After a moment, she stood up, letting the hem of her nightgown fall back down to her knees, but not pulling the top up.

She walked over and lay down on a bed.  “Come over here” I stood up, conscious of my erection, and walked naked to the side of the bed. I looked down at Mrs. O and she smiled.  I noticed her breasts had flattened out, moving outward, but she was still flushed and her nipples were still hard.  “Straddle my chest” she directed.  So I got on the bed, partially kneeling with a knee on either side of her ribcage. My hard penis was jutting upward and forward over her sternum.  She reached with one hand and wrapped it around my erection, squeezing the head slightly, and using her thumb to swirl the increasing precum around.  It felt amazing.

With her other hand, she pushed one boob toward my penis, and I watched as she gently touched the nipple to the shaft of my penis, lightly stroking it while she stared intently at the interaction.  Then she laid back and smiled. She spit loudly into her left hand, wrapped it around the shaft of my penis, pulling it slightly downward, and she began a gentle twisting motion, letting the lubricated palm slide up my shaft until her thumb hit the base of my penis’ head, then she slide back down.  With her other hand, she wrapped it around the swollen head, sliding and twisting, small movements up and down, letting her fingers-slick with my precum-slide along.  I looked down as she did this, watching her boobs as she used both hands to masturbate me.

It was no more than 30 seconds before I could feel a swelling sensation, and a strong twitching.  “Uh… Mrs. O! I’m gonna finish!” I tried to move, assuming that’s what she’d want, but she held me tight, continuing to work me.

I groaned and exhaled as I felt the first pulse, and watched a spurt of semen land right in the hollow at the base of her neck.  She had stopped the sliding motion, and now had a tight grip with both hands, squeezing and almost pulling with each pulse.  It was an enormous cum, the kind where you can feel it moving through your dick. The next two spurts caught her on the chin and jaw. I think she must have then lowered the angle, since the rest of the ejaculations formed a pool on her chest.  I felt like it would never end; I shut kept pumping out cum.  She never loosened her grip, expertly timing each squeeze like she was milking me. When I was done, I just sat there, drained.

I figured Mrs. O would ask for a towel, or do something else to get the gobs of cum off her chin and body.  Instead, she did something incredible, something I’ve seen no other woman do.  She delicately wiped my cum off her jaw and chin with her fingers, then licked the cum from her fingers.  Then she took both hands and began spreading the cum on her neck and chest, rubbing on her boobs and chest like it was lotion, until there was a light sheen on her skin.  When she was done, she laid there, looking it me.

“You should get going” she said.

“”Oh, yeah.”  I got up, pulled on my briefs shorts and t-shirt.  Mrs. O got up, pulled her nightgown back up, and put on her bathrobe from the closet.  She went out into the hallway, and looking carefully each direction.

“Okay.  You need to go to your room. It’s clear now.  And this is going to be our little secret.” She gave me a piercing look as I walked out into the hallway.  Her door immediately shut behind me.

I must have spent the next 4 months having out at my friend’s house, desperately hoping for a repeat.  It didn’t happen.  I’d smile, try to be charming, but nothing came of it.  Mrs. O acted exactly the same as before the big night.  No secret smiles, no winks, absolutely nothing.  In a way, it was extremely frustrating, and more than a little maddening. But at the end, I left for college.

The odd thing was that the same dynamic of her being polite and friendly, but nothing more, continued for years throughout college.  My friend got married right after college and moved to Boston, so I never saw her.  But about three years after I graduated, I ran into Mrs. O at a real estate conference in Houston.  I was in finance, and she was divorced, working for a mortgage broker.  That weekend was weirder, wilder, and involved very little for Solo Touch.  Story for another time, I guess.