Sherry's Problem

Info silverhawk
09 Oct. '17

Sherry was in her late forties at the time I knew her.  She was the shipping supervisor, and I supervised a department in manufacturing, so we worked pretty closely most of the time.  Since I always tried hard to make sure she made her shipments, Sherry and I became good friends, After a year or so, she started sitting with me when she ate her lunch.

I liked eating lunch and talking with Sherry.  She mostly wore jeans and T-shirts to work, and she seemed to like flimsy bras.  That was reason enough to enjoy her company, but she did this thing…well, if you had a deep voice like I do, and you talked to her, her nipples would get hard.  I figured she knew all about that or she would have done something to keep them from showing.  

Sherry was usually a pretty happy person around me, but one Friday, she seemed to be in a rotten mood.  I went up to talk to her about a shipment we were going to miss, and she damn near cut my head off.

“Son of a bitch, Tom, you knew that shipment had to go.  What the hell have you guys been doing out there…playing with yourselves?

Sherry wasn’t bashful about saying what she thought, and I was glad nobody else was in the office at that time.  Talk like that could have gotten her fired.  I apologized and left after promising to get the shipment done in time for an expedited truck that night.

About two, I decided to have a smoke and walked out on the shipping dock before lighting up.  I’d just taken the first pull when Sherry walked up beside me and asked for a light.  She inhaled deeply and let the smoke trickle out through her lips, then handed my lighter back to me.

“Thanks Tom.  After what I did to you this morning, I’m surprised you didn’t run my fat ass off.”

“Ah, I’ve been chewed worse than that and lived, and it isn’t.”

“Isn’t what?”

I took another pull on my cigarette.  “It isn’t fat.”

Sherry smiled.  “That’s not what Jerry said.”

“Jerry, your husband?”

“Yeah.  He’s been like that lately.”

Sherry took another drag on her cigarette, then turned to me.  She looked more than a little upset.

“Tom, you’re probably the best male friend I have.  Can I ask you something and get a straight answer.”

“Sure, as straight as I can give you.”

“Well, I don’t seem to be able to get Jerry…well, you know…excited.  At first, I thought he was just tired.  He’s been working lots of hours, but that stopped a few weeks ago.  I don’t think he’s really looked at me in months. Do you think he’s having an affair?”

Well, like I would know if he was or not.  Still, Sherry was obviously upset, and I wanted to help her as much as I could.

“Probably not.  He’s about fifty, right?  My dad’s about that age and he had kinda the same problem.  He ought to go to a doctor like my dad did.  It’s probably nothing, but it wouldn’t hurt to know for sure.  If it’s just his age, they have pills to take care of that now.  Since Dad went to the doc, Mom’s been smiling more than she has in years.

Sherry laughed, but got serious again.

“I tried to tell him that, but I think he’s too embarrassed to go.  He used to not have any trouble at all.  All I had to do was walk through the living room in my bra and panties, and it was off to bed we’d go.  Last night, I walked out to his workshop bare-ass naked and know what he said?  He said I should get my fat ass back in the house before one of the neighbors saw me.”

I had this image of Sherry naked with her big nipples standing proud off her breasts.  I wouldn’t have minded being their neighbor at all if she was going to do that often.  I must have had a smile on my face, because Sherry slapped me on the arm.

“Hey, I know what you’re thinking and I’m not sure I like it.  So how do I get Jerry to the doctor?”

“Uh…I don’t know.  I don’t like doctors myself.  Maybe if you talked to your doctor, he could suggest something.”

She stomped out her cigarette and kicked the butt into the storm drain.  “He’s a she, and I might do that.  Thanks Tom.”

After a week or so, Sherry seemed to be back to her normal self.  I was the only one who knew her situation, so I could see that she was still stressed, but she covered it up pretty well.  Well, that is, until her car died.  She called me at work one morning and told me she wouldn’t be in, and could I do her a big favor and pick her up the next morning.  It sounded like she was in tears.  I agreed, and she gave me the address.  It was only a block off my normal route to the plant, so it wasn’t an inconvenience.

The second day I took her to work, she was dressed up in a skirt and blouse.  I didn’t get the chance to ask why, because as soon as she got in my truck, she told me she either needed a new engine or a new car.  I said that was a bummer, but that she could keep riding with me as long as she needed to.  

“Well, I hate to ask this, but I made that appointment with my doctor like you suggested.  That’s why I’m dressed like this,  and…well…would it be possible for you to take me there after work?”

I didn’t have anything better to do, so I said yes.  The trip to the doctor took over an hour, and Sherry didn’t seem too happy when she got back in the car.

“Well, that was a bust.  I sat in the waiting room for forty-five minutes with a bunch of pregnant women.  When I finally got to talk to her, she said Jerry probably just has E.D. and unless he goes in for an exam, no doctor would give him anything.”

Sherry was silent the rest of the way to her house.  She was pretty quiet for the next couple of days too, and then I noticed a change.  When I talked to her, her nipples seemed to get even bigger, and there was this look in her eyes I hadn’t seen before.   She seemed to be a lot friendlier too.

When I took her home that Friday, she didn’t get out of the car as soon as I pulled in the drive.  Instead, she put her hand on my arm and smiled.

“Tom, I don’t know how to thank you for what you’ve done for me this week.  You won’t let me pay you for gas.  Would you like to come in for a cup of coffee or something?  It’s the least I can do.”

At that time in my life, I wasn’t very quick on the uptake, as they say.  I didn’t notice that Jerry’s car wasn’t in the drive like it always had been before, and I didn’t pick up on the little change in Sherry’s voice when she said “or something”.  I just followed her to her door and went inside.  Sherry dropped her purse on the coffee table and called back over her shoulder as she walked away.

“Have a seat on the couch, Tom.  I’ll start the pot, and then I’m going to change clothes while it’s brewing.  The TV remote’s on the table if you want to watch something.”

The only thing on her TV was news, so I switched it back off.  Jerry was a woodworker, and there were a couple of magazines on the table.  When Sherry came back in the living room, I was reading about the various properties of different hardwoods.  I turned to face her and what I saw made me forget all about hardwood except the wood that was growing hard in my jeans.

Sherry had changed clothes, all right.  I was kinda expecting more jeans and another T-shirt, because that’s what she always wore at work.  I wasn’t expecting those jeans to be cut off all the way to the crotch seam, and I sure as hell wasn’t expecting her T-shirt to be scooped deep in front.  The two large bumps barely covered by the front made me pretty sure she wasn’t wearing a bra.  It was starting to sink in that she hadn’t changed clothes just to get more comfortable.  Sherry just looked at me looking at her and then laughed.

“You look like you’ve never seen a woman before.”

“Well, I have, but usually they’re dressed.”

“I’m dressed, see?”  Sherry held up her arms and turned slowly all the way around.  “Don’t you like my outfit?”

“Oh, I like the outfit.  It’s what the outfit’s going to do that worries me.”

“And what’s my little shorts and top going to do that’s so bad?  It’s what I wear around the house all the time.  Jerry doesn’t even notice anymore and it’s nice that you did. I’ll go get our coffee now.”

I sure as hell was noticing.  I hadn’t realized Sherry had quite the figure I was seeing.  The jeans she wore to work were pretty loose fitting, so I had to imagine how her legs and ass looked.  I didn’t have to imagine anything now, and Sherry was pretty hot.  Her legs weren’t really long, but they were slender and joined up to her round little ass cheeks in those soft creases I love to fondle.  It was about that time that my cock started hinting that Sherry was turning me on.  Well, it was more of a throbbing scream than just a hint.

One minute, my cock was soft, then after I watched Sherry walk to her kitchen, it was rock hard and making a bulge down the leg of my jeans.  There wasn’t much I could do about it, because just as I reached down to get things readjusted, Sherry walked back in the room with two cups in her hand.  The only thing I could do was sit down on the couch.

“Here ya go.  Cream and sugar, right?”

She bent over to hand me the cup, and her breasts rolled up to the low neckline of her T-shirt enough that I could just see the tip of one swollen nipple.  My cock strained against the leg of my jeans.

Sherry walked to the chair beside the couch and sat down.  I was taking a sip of my coffee at that moment, and damn near choked.  Sherry was sitting with her legs apart, and  I was looking at a small patch of dark hair and one very puffy, very pink pussy lip.  Between the sight of her crotch and the pain I was starting to feel in my own, I almost didn’t hear what she was saying.

“I want to tell you again how much I appreciate your taking me back and forth to work.  Jerry’s going to get me a new car this weekend, so I’ll be able to get my ass to work by myself again.  I think I’ll miss riding with you every day, though.  It’s kind of nice having someone to talk to, don’t you think?”

“Uh…oh…yeah.  I enjoyed having you riding along, and it wasn’t any trouble really.  I was glad to help you out.”

“Wish you could help me with my other problem.”

“Jerry still didn’t go see the doc?”

“No.   I told him what mine said, and he just nodded and went out to his workshop.  I’m starting to think it’s just me.  I mean, things aren’t as tight as before the kids, and I’ve gained a few pounds.  I think I just don’t interest him anymore.”

“Sherry, I can’t see how it could be you. You look great.”

As soon as I said it I knew I was in trouble.

“You really think so?”

“Yes, I do.”

“So, if you just saw me at the grocery store, or in a bar, you’d think about…about sleeping with me?”

“Well…yeah…if I didn’t know you.”

“And since you do know me…”

“Well, Sherry, I don’t think office affairs really ever work.  Something always happens, and then –“

“I’m not talking about romance, Tom.  I’m talking about sex.  I think you’re afraid to say what that bulge in your pants is telling me.”

I tried to get back in control of the situation.

“OK, you got me there, but just because I’m aroused doesn’t mean I want to sleep with you.”

“But if you had the chance and nobody would care, would you?”

“Yeah…I suppose I’d think about it.”

Sherry reached down and pulled the T-shirt over her head.  Her breasts bobbed gently as she threw it on the coffee table.  They bobbed again when she kicked off her running shoes and then unzipped the shorts.  They bobbed a lot as she worked her ass back and forth to get the shorts off.  As I’d guessed, she wasn’t wearing any panties.  Sherry gently rubbed her breasts.

“Tom, Jerry hasn’t touched me in over six months.  You’ve got about five seconds to think about it before I jump on you, so either get out of those clothes or get up and leave.”

Well, being the young, horny, but stupid guy that I was, I unbuttoned my shirt and unbuckled my belt.  I didn’t have pull down my jeans.  Sherry did that for me while I was trying to get my shirt off.

I think she was on her knees before my shirt hit the floor.  She unzipped my jeans and yanked them down around my ankles.  While I tried to step out of them, she grabbed the waistband of my shorts with both hands and pulled.  My raging hardon bobbed up in her face and she grabbed it with both hands.  After a few soft strokes, she sort of engulfed my swollen cockhead with her lips, and damn, what lips she had too.  Today, I’ve lost some of my holding power, and she’d have me cumming in a minute or so.  Back then, it still took lots of willpower to just relax and enjoy what she was doing.  

I reached down and brushed my fingertip over Sherry’s right nipple.  Her shoulders shook and a little moan burst out around my cock.  I lightly pinched that nipple and Sherry groaned, “God, Tom, I need to be fucked so bad.”

When I pulled her up to face me, Sherry planted a kiss on my mouth that almost suffocated me.  Her tongue licked my bottom lip, then plunged between my teeth and wrapped around my own tongue.  It felt so good I slipped my hand down to her dark bush and slipped a finger between her lips.  Sherry was right – she did need to be fucked.  She was so wet she was almost dripping on my hand.  I broke the kiss and pushed her back on the couch.

Sherry laid there with one foot on the back of the couch and the other resting on the edge of the cushion.  Her pussy was open and glistening with her nectar.  I intended to sample that treat, and I intended to sample it then.  As soon as my tongue touched her, Sherry moaned again.  When I slipped my tongue into her opening and then rasped it up over her swollen inner lips she gasped.

“Oh God, yes.”

Well, Sherry was already wet, but she got wetter.  As I licked her, I could feel her pussy contracting, and each time, I felt wet warmth on my chin.  She was so hot, I think if her husband had walked in the door right then, she’d have told him to go fuck himself and leave us alone.  

I hadn’t really wanted her to cum that way, but cum she did.  I’m just not sure how many times. I found her clit and sucked on it for a few seconds and Sherry exploded. It was a whole bunch of moans and little cries and her hands on my head pulling me tighter into her pussy, and her pussy contracting on my tongue and all that warm wetness flowing all over both of us.  She didn’t push my head away so I kept on licking from her opening to her clit with a few gentle sucks every now and them.  When she finally pushed gently on my head, my tongue was starting to ache and my face was wet all over.  

Sherry didn’t say anything for a while.  She just pulled on my shoulders until I moved on top of her.  I felt her hand slide between us and grab my cock.  She rubbed my cock head between her wet, slippery pussy lips and then moved it to her entrance…Her hips rocked up, and my cock slid inside her.

Sherry was tight, tighter than some of the girls I was dating at the time in fact, and she felt like heaven around my cock.  Her big nipples felt pretty good against my chest too.  She evidently liked moving them back and forth across the hair on my chest, because that’s what she was doing.  It was doing something to her.  I felt her belly roll against mine every time she moved her nipples.

I slowly stroked my cock in and out of her and Sherry murmured, “Oh that’s it, Honey.  That feels great. “  As I continued to fuck her slowly, Sherry crossed her legs over my back.  She was sort of hanging there and with every stroke, she pushed her pussy over my cock.  That was putting my cock so deep inside her that my balls were bumping her ass.

Sherry gently dragged her nails over my back and then down to my ass.  She grabbed an ass cheek with each hand and dug those nails in.  It didn’t hurt.  In fact, it felt pretty great.  It felt so great I was a little disappointed when she started moving her hands around again.  That disappointment all evaporated when she touched my asshole with her fingertip.  I caught my breath and Sherry whispered into my ear.

“Like that, do you?”

“And how.”

“Do the same to me, and you’ll make me cum again.”

Well, I guess it was a night for firsts – the first time I’d fucked a married woman, the first time a woman had felt my asshole, and now, the first time I’d fingered a woman’s.  When I touched her tight little rosebud, I thought Sherry was going to jump out from under me.  Her hips jerked and then pushed back into my hand.  She was so wet everywhere, my fingertip sort of slipped right inside her up to the first knuckle.  I pulled it back out quickly.

“Oh, God… yes. Honey…again, and leave it in”

Sherry stopped talking after that, but she was panting so hard I don’t know how she’d have been able to say anything anyway.  A little while later, I felt Sherry tense up, then begin to arch up off the couch.  Her panting stopped as she groaned, then gasped, “Ohhhh…now, Honey, now.”

That did it for me.  I remember hoping she was on the pill, because I couldn’t have pulled out to save my life.  Sherry rocked her hips up to meet my thrust and cried out just when I shot my seed deep inside her.  Her hips seemed to be completely out of her control.  They were jerking up and down and forcing my cock in and out of her.  All I could do was try to keep up with her.  It was a hard task considering that I was cumming like crazy myself.  I thought I was done until Sherry slipped her finger back to my asshole and pushed.  She must have picked up some of the fluid from her thighs because it slipped right in.  My last spurt was unbelievable, and left me gasping for breath.

Sherry giggled.  “I thought you might like that.”  She let her legs fall beside mine and pulled me down to lay on top of her.  “I love feeling a man’s weight on top of me afterward.”

“Yeah, it feels pretty good on this end too.”

Sherry sighed. “Let’s just stay this way all night.”

“Well, uh, I’d love to, but won’t Jerry be coming home?”

“Not until Monday morning.  He’s off to some woodworking show somewhere.  So, see, I get you all weekend all to myself…if you’ll stay.”

“What if he finds out?”

Sherry looked up at me and smiled.  “Well, he already knows, in a way.  Last week, I told him if he didn’t start taking care of me, I’d find somebody who would.  We talked about it.  He still loves me, in his own way, and he understands what I need.   He said since he couldn’t anymore, if it made me happy to go ahead.”  She smiled again.  “You made me really happy.”

Well, that weekend turned into an unbelievable couple of years.  It was a little strange to be having sex with no emotional tangles to work through, but Sherry didn’t want any involvement with me other than sex.  If that sex hadn’t been so fantastic, I might have had second thoughts.  I think she was a little more involved than she let on, though.  There were tears in her eyes when she told me she’d been promoted and was being transferred to another state.  

We still keep in touch, although we haven’t been together since I met Jenny.  Sherry says she couldn’t do that to another woman.  I suppose she right.  I love Jenny all to pieces, but sometimes I miss Sherry too.  What we had was a kind of love, just not the same kind of love Jenny and I have.

When I first met her, Sherry seemed a little hard and not very feminine. At that time, I wouldn’t have believed she could be like she really was.  I finally figured out it was because of the men she had to deal with.  If she’d have been the sensuous and desirable Sherry I knew, they’d have tried to push her around instead of working with her.  I guess we all live and learn.  I’m just happy I lived to learn about Sherry.