Sherry

"Well, I hear what you're saying. Sandy tells me the same thing. Maybe I'll do that sometime. Some of Beth's clothes are like that aren't they? I saw some today that fit me better, snugger than any I have. And lots of the dresses were shorter. Maybe I will. I'll look at some tomorrow. Well, I guess I should get out of this swimsuit and take a shower and get ready for bed. It has been a very long day."

"Wait, try on one more. It's still early. We can sleep late tomorrow. Didn't your therapist tell you to try new things and push the envelope? C'mon, just one more tonight."

I figured this one was about as risqué as I would ever get and I couldn't imagine wearing something even more revealing and I also supposed he didn't want anything less so. I was also concerned about somehow using a man whose wife died a few months ago so it had probably been a long time since he'd had sex. Was it fair to him to do this? On the other hand, I'd NEVER had sex so...I was confused about what I wanted but I was enjoying it so much.

"Ok, Paul, maybe one more. But I'll let you pick the last one out. I've separated the ones that I think will fit me, not that I'd wear all of them but they pretty much fit. They're on the bench in Beth's closet. "

...

Paul

She had selected eight suits, from tiny bikinis to the much more modest one-piece suits that Beth would sometimes wear at the pool or on the boat when we had other people around. I picked out a black bikini, not one of the micro ones but one that was a little more modest. I didn't know if she'd have the nerve to put it on or not. I took it out to her.

As I handed it to her, she had a very surprised look on her face. "You are kidding me. I can't wear a bikini. My underwear is way bigger than this. I can assure you, you don't want to see that much of my body. Even I don't want to see that much of my body."

"Well, you're dead wrong about that. You have a very nice body and I'm be pleased to see that much of it. But, I don't want you to do anything that makes you uncomfortable."

"Thanks Paul, I appreciate that. I really don't feel comfortable wearing this, at least in front of you or anyone else for that matter. Maybe I can find something else."

I tried not to but I probably sounded a little piqued in my response. "No, that's ok Sherry. You were right. It is getting late and maybe we should just go to bed. I enjoyed seeing those other suits though. Please take all of them with you. I think you enjoy wearing some of them at least. And you can try to rest on when you're alone if you like. I'm going to go to finish reading the paper and then take a shower and go to bed. Goodnight and sleep well."

I gave her a kiss on the cheek as I often do at bedtime. As usual she stiffened but then seemed to relax and she put her arms around me and pulled me close. "Thanks, Paul, for everything. I had a great time today and tonight. Thanks for saying I looked good. It meant a lot."

I read the paper for a few minutes and then started turning out the downstairs lights.

Sherry

I felt so bad I'd upset him. I was just afraid of where this was going. It would have been easy to lead him on and then I figured I'd just chicken out at some point, leaving him more disappointed.

I went back to their bedroom to pull off the suit I had on and then take a shower. When I stepped out of it, I was amazed to see a big dark spot in the crotch where I had leaked. I put my fingers on my pussy lips and couldn't believe how much fluid was seeping from me...it had run down one of my legs. I wondered if Paul could see that. God, what was coming over me? I wish I had been like other women and was able to just let go. But I was afraid that I'd screw it all up and run away at the exact wrong time. But, it wouldn't hurt to go a little further would it? To give us both something to think about?

...

Paul

"Paul? Are you still down here?"

I had just turned out the lamp when I heard Sherry so I quickly turned it back on. She was standing there in her robe.

"Paul, I just thought that...well, I'm sorry for how I acted so I just wanted to...well."

And she opened the robe and let it fall to the floor. She had on an even tinier bikini than the one I'd brought down earlier. It wasn't the tiny micro-bikini but it was one that was very, very revealing. I was stunned and I think it showed.

It was a silky light green fabric. The bra had a hard time containing her big tits; a thin strip over each breast barely covered her nipples and aureoles but left a lot exposed. Her nipples were hard and swollen. The bottom revealed pubic hair showing over the top and around the leg-holes. She turned and while it wasn't quite a thong, it only covered a small section of each ass-cheek. As she turned around, whereas before she had her shoulders hunched as if to symbolically cover her breasts, this time, she put her hands on her hips as if to emphasize them. She just stood there looking at me. She had a very full, voluptuous body. Even her midsection, while certainly not washboard-flat, was nicely rounded but not flabby looking. This was a lot of woman.

"So, Paul, you're not saying anything. How does this one look? Say something."

I gasped, "holy fu... God, sorry Sherry, I shouldn't have said that but oh my God, you look amazing. I don't know what to say except that...that you...you, well, you look really sexy and hot. I love it."

She responded, "I know I am overweight but I'm trying. I know my body has too many bulges and rolls, but seriously, do I look nice? Are you really telling the truth? Do you think I look...well...hot? I can't believe that. I have never, ever, never considered myself sexy. Maybe I shouldn't say this but for a long, long time, whenever I would get...accidentally get aroused, I would be ashamed of it, thinking I was doing something wrong. And I wouldn't...couldn't...look at my body. I never looked in the mirror. And to think some man thinks I look sexy. Well, it must be the drinks talking." She chuckled. "When you wake up sober tomorrow morning, you'll change your mind."

"Well, I am not drunk Sherry. And when I go to bed tonight and wake up tomorrow morning, I will just remember how really, really sexy you look...are...tonight. I know it is easy to say, but don't be ashamed of your body. You have a lovely body and lovely face. Permit me to say that your breasts are wonderful, I love your legs, and well...I won't tell you what I think about the rest of you. I just want you to know something. I can't speak for all the other men in the world or any of them for that matter. But, speaking only for this man, if I were 20 years younger, I'd be all over you if you'd let me. I would so anything I could to seduce you. You are smart, beautiful, good and kind, and believe me, you have a great body and are a very desirable woman. And I mean all that from the bottom of my heart."

She blushed, "thank you so much Paul. You can't believe how good that makes me feel, how good it would make any woman feel. I've never had this feeling before, standing before a man, almost naked, with him saying how good...desirable...she looks. I won't ever forget that, and I won't ever forget this night."

She then came over and said, "good night Paul and thank you again." She kissed me on the cheek and surprisingly pressed her body to mine. This time it was extra special, and extra erotic because of the outfit she had on.

...

Sherry

How could this evening be any better, or in other ways, worse? I was scared stiff of what was going on between Paul and me. I felt bad leading him on knowing that he was needy and that I might not be able to go through with it even though I started it. On the other hand, I was so...horny...and wanted more. I was very frustrated and angry at myself. But tonight I'd done more than I ever had so that is some progress. I know he was turned on...which is what I intended I guess. Otherwise why would I put on such a skimpy suit that showed lots more than it hid?

After my shower, I got in bed nude, one of the few times in my life I intended to sleep naked. I had taken a cool shower but my lust was not diminished in the least. I tried to read but without even thinking about it, my fingers were playing in my pubic hairs. When I thought about that I was embarrassed by how much I'd shown before; I should have shaved or trimmed but I didn't think I would be showing everything I had. I could almost feel the heat rising from between my legs and when I put my hand on my slit I could feel the wetness, and it was slick, not the water from the shower. I was still dripping pussy juices!

I slipped on a pair of panties because I didn't want to leak on the bed but as I tried to return to my reading, the ache wouldn't go away and I found my hand over my crotch...the dampness was seeping through my panties! Unable to get my mind on anything other than my lust, I finally pushed the cover back and opened my legs. I imagined Paul looking at me as he rubbed his cock. I thought about how it would feel to have him see me naked, all spread out, eyes clouded with desire, panting for sex. I slipped my panties down my legs and after I pushed them away, I opened my legs and caressed. My closed lips were swollen. I have big labia anyway but now, they were engorged, fat and puffy. I opened my slit, slipped one finger and then two inside and pulled them out and saw a string of sex fluid webbing my fingers. I pulled my lips apart even further and thought about Paul doing it, opening me, looking at it, between my legs, lusting for my hot cunt! (I'd never used that word before but now it seemed okay.) I ran my fingers up and down and slipped one inside. My hips rose to thrust up like I was offering it to Paul. With my other hand, I ran a finger around my clit, using the seeping pussy juice to lubricate it. I had to stifle an urge to yell but even then I was moaning, rubbing around my clit and muttering, "Paul, fuck me, fuck me, fuck me...fuck me." My tits were bobbing I was moving around so much, writhing, begging for Paul's cock like a hot fucking slut (never called myself that either.) As I started to cum, my body was quivering and I was sobbing with desire. God, I was a woman that needed to be fucked, fucked hard, and fucked often. Fucked with Paul's big, hard, throbbing dick. Fucked like an animal. I clinched my legs together and pressed my open hand to my pussy and felt the contractions of a wave of orgasms. I have no idea how many.

A little while later, the lust was slaked a bit but still there so I rubbed my needy pussy again, had another orgasm...and then slept.

...

Paul

Am I taking advantage of a damaged woman? Was it fair for a much older man to keep encouraging her to do something that may worsen her fears? Should I talk to her? Should I tell her that we shouldn't be doing this? But was that fair? Maybe it was helping to see herself as a sexual being. Would she feel rejected if I dissuaded her?

I mused about these questions as I tried to fall asleep. I didn't come up any answers to those and other questions, partially because my mind kept returning to the image of her standing before me, nearly naked, with big beautiful tits and all that pubic hair sticking out of the bottom of her swimsuit. I imagined unhooking her top, pulling it away and hefting her big breasts to my lips and sucking those hardened, huge nipples. Then rub my fingers around the leg-holes of the bottom to feel the hair. My wife Beth, at my request, would never trim her pubic hair because of how much I liked it and Sherry looked at least as hairy as Beth. I used to love to eat Beth's pussy and feel the hairs around my cheeks and I imagined doing the same thing with Sherry. I thought about how she would smell and how wet she got.

"Sherry, I need to lick and fuck your hot pussy," I said, almost surprised that I acknowledged it out loud. "Tell me you need it Sherry, how much you need a cock, my cock, inside you."

I looked down at my cock, erect and throbbing. It wasn't any longer than average or at least what I'd read average to be, but I felt it was definitely thicker. And when it got hard, it was taut like a steel cable. I couldn't imagine how it would be to slide it into Sherry. Since she was a virgin, I wondered if it would hurt too much and scare her, or remind her of what her father did to her. I know that he inserted things inside her, his fingers and a dildo...she told me that, so her hymen was probably not intact but was there anything inside her since? Maybe, if we ever did anything I could just lick her pussy, or would she even want that?

As much as I had all those questions, I was also crazed with lust for her. I put some saliva on my fingers and rubbed them over the mushroomed head of my cock. With the other hand, I held my shaft. Then I did what Beth used to do sometimes - wet my cock and then put a hand on each side and pull then up slowly, caressing the shaft. She said she wanted to feel the pulse and heat. I stroked like that with my eyes closed, remembering Beth doing it and thinking about Sherry doing it. I imagined Sherry making me cum and then licking it off. Or, getting to the point I was almost cumming and spreading her hairy pussy to take me inside. God, I needed this so much. It felt amazing. My hips started to lift off the bed as my slick cock glided between my hands. Sherry could probably hear my moaning and grunting but I was too excited to even notice what I was doing. When I felt the eruption beginning, I put both hand over the head of my cock and felt the spurts splash into my palms. As my spasms subsided, my cock, hands and pubic hair was covered in white, thick cum.

Finally, I fell asleep.

The next morning, I got out early to go into the office for a few hours. I got a text from Sherry mid-morning saying she had a few errands to run and would see me in the afternoon. I had a late lunch and got home around 2. After a quick shower and change of clothes, I heard the garage door open.

When I came down, I was very surprised to see a changed Sherry. She had gotten a new hairstyle and had on a pair of nice jeans and one of Beth's blouses that was tight around the chest and accentuated her breasts very well. Her hair was down around her shoulders; it looked like it had some blondish highlights in it.

"Wow, I see you've had a busy morning. I love your hair like that. That looks just right on you." She was wearing a bit of makeup as well; not that much but just some things that brought our her pretty eyes and cheekbones. "Those clothes look great on you. What prompted all this?"

She smiled, "just trying to spruce up a bit. If I'm going to push the envelope, I figured I might need to get all the help I can. Besides, sometimes a woman just needs a little bit of a make-over."

"Well, the old Sherry was great but I really like the new one as well. You look beautiful. How about it? Would you like to go to a movie or something? Maybe take a swim?"

"Nope, I know you're trying to get out of it, but we need to finish going through Beth's things. Let's get to work."

So for the next three hours we went through the rest of the closet. As before, she mainly went through the clothes and shoes and I hauled them to the garage. A few times, we were in the closet together and I had the distinct impression that she deliberately brushed against me. I may have been wrong but either way, those big, soft breasts felt good against my arm and once across my chest as she reached up for some boxes on an upper shelf.

She opened one of them when I was still in the closet. I heard her gasp and looked and saw it was where Beth stored her erotic lingerie. The box was full of negligees, baby dolls, crotchless panties, all kinds of sheer fabrics, thongs etc., including a few items that we used for role-playing. It also contained some things - handcuffs, velvet ropes, etc. that we used for light S&M that we enjoyed occasionally. Sherry quickly handed the box to me. I moved it to my closet; I would decide what to do with it later. The lingerie box stayed in the closet.

"None of my business Paul, but I don't think I would donate those to the women's shelter if I were you. You may get arrested," she teased with a smile.

"Yeah, guess you're right," I replied, "better hold those back."

We finally finished and I had everything stacked in the garage to take to the donation sites later. We decided to take a quick shower and go out to dinner.

During the meal, we finally got around to talking about what happened last night.

"Paul, I need to talk to you a little bit. I...I hope you didn't think that last night...that I was too forward or something, trying on those things. I'm not sure what got into me. I have never done anything like that and...and well, I never even imagined doing that, particularly with someone like you." As she saw me smile, she quickly added, "I don't mean that like it sounded. I mean that I don't want you to think...I admire and love you so much I don't want you to think I was...er...coming on to you or something. Not that...I mean...you are attractive and all. God, I am making a mess of this. I don't really know what I mean but I just don't want you to think I am some sex-crazed woman or something. I know how it must have looked, me wearing those skimpy clothes."

I took her hand...she didn't resist. "Sherry, I would never think less of you. I loved last night. I think it showed a lot of trust in me to do that. I know it wasn't easy for you. But, I did enjoy it...a lot. I don't quite know how to say this but it...I was excited to see you in those things. It was...I mean, I liked it. Wow, I'm not doing any better at this than you were."

She laughed. "Paul, I have to ask you something really serious. Something very important to me so I want to know the absolute truth, no lies, no falseness. Don't worry about offending me. Will you tell me the straight truth?"

I replied that I would and I meant it.

Did you really...really...find me attractive? Did you think I was sexy at all? Remember, the truth. I know I shouldn't ask you this and I don't want to know if YOU were sexually attracted to me. I mean do you think other men would? God, what an awkward question," she said blushingly.

I looked her in the eye. "Sherry, I think any warm-blooded man would find you sexy and attractive. And Sherry...I know I do. I find you very sexy. I shouldn't say this...well, I won't say what I was about to but believe me about this...you are a very desirable woman, not just to most any man but to me as well."

"Go, thank you for that. You don't know how new a feeling this is for me; what it means when you say it. But, what were you about to say you didn't say? It's not fair; you have to tell me. You promised to tell me the whole truth."

"What I meant to say, that I shouldn't say, was that I had a hard time getting to sleep last night thinking about you, remembering how you looked, your body...everything about you..." I trailed off.

She looked like she might cry. "Thank you so much for that Paul. Thank you for everything you just said. It makes me feel like a real woman. It makes me feel good. Paul, I have to say...well, I had a hard time getting to sleep as well. I was...was excited by thinking about you looking at me like a man looks at a woman, not a father figure looking at a child. Believe me I tossed and turned as well as you. Biologically I have had those kinds of feelings...well, a lot, and a lot more lately..." she paused.

We were both flustered with the emotion. I was starting to comment on the meal when Sherry interrupted me.

"Paul, can we go home soon?" she asked.

I paid the check and we drove home. After we went inside, I asked her if she was going to bed or would she back down stairs. If she was going to stay up a while, I'd fix us a drink or some tea. She said a drink would be lovely and she'd be back down soon.