Working Late

"I guess that's not strictly what happened then" interjected Laura with a chuckle.

"No... quite," Ben replied with a grin "...although she never knew that. As I was settling in I noticed that she had left some of her underthings to dry on an airing rack by the heater vent. This wasn't uncommon, especially in the winter, however this was the first time I had really taken an interest in them."

"What sort of things were they?" asked Laura.

"They were fairly normal middle aged ladies underwear. Full brief panties in pastel shades with a bit of a lacy trim, a couple of simple bras, and then the object of my interest, several pairs of pantyhose." Ben recalled with a slight glint in his eye. "I walked over and picked them up and the feeling of them was amazing. So light and flimsy, and yet stretchy and strong. I was fascinated with them. I must have played with them for quite a while, just running them through my hands, putting my hands inside the leg, touching my face through the fabric. The sensations were electric."

"That sounds exhilarating." said Laura as she took another sip of her whisky.

"It was but I don't think there was a sexual component to it yet." Ben replied "At least not one that I was consciously aware of. I was just enjoying the feeling of the material, and at least some of it was the fact that these were my moms secret things that should never normally get seen, and I was able to play with them without anyone knowing."

"Parents always know, you know." Laura replies with a sly smile.

"Maybe" said Ben "But at least at the time I had no awareness of that fact, so I was in my own little world."

"So did you try them on?"

"Not that time no." said Ben "I think I instinctively knew that trying them on would stretch them out and make it obvious I had been poking around so I didn't go beyond just playing with them in my hand."

"So when did you first try on a pair?" asked Laura

"Well now that I think about it," Ben started "after that first exposure I made a point of looking out for the pantyhose when they were going to go into the washing. I wanted to try and have another play with them and I figured that if they were in the washing pile then any stretching or crumpling I might do to them would be shaken out in the wash, and any damage could be explained away as being from the machine. This was easier said than done as my mom was very fastidious at taking clothing to the washing machine and washing it almost straight away. Then one weekend she had to urgently go to her sister's place a few hours away. I guess it was some kind of relationship emergency and I don't think she wanted to have to explain it all to me, so she left me alone in the house for the day. This time, however, because she had to go quickly, she didn't have time to set the washing going and asked me to do it for her. Obviously I jumped at the chance to get up close with her pantyhose. So I told her that was no problem, while still trying to sound dismayed at having to do housework."

"Did you play with her other worn underwear too?"

"No, I didn't really acquire an interest in other lingerie until a bit later on. For now I was solely focused on playing with the pantyhose. So after she left, I waited 20 minutes or so to make sure she was well on her way, and then headed to the laundry room to start sorting the washing. I rummaged through the pile and found 3 pairs of worn pantyhose so I put them to one side and sorted the rest of the washing into the washer. I then took the hose back to my room."

Laura took another sip of her drink and said "Go on..."

"So when I got to my room I sat there just feeling the nylon for ages. The three different pairs were all slightly different. I have come to realize that one pair was an expensive pair, probably Woolford's, or something, so very finely knit and really smooth, and the others were a bit coarser, probably a cheaper brand. Either way they were fantastic to feel. Then, as I was putting my hands inside and feeling the nylon rub against itself, I realized that they are designed to be worn, and that I could actually wear them without any repercussions, so I got undressed and slowly started to slide them onto my legs one at a time. I knew how to do this as I had seen my mom do this many times in the past. I carefully rolled the leg all the way up into itself and placed my foot into the hole, then slipped the nylon up the rest of my leg to the knee. Even just doing this much the feeling was wonderful. I repeated the same steps on the other leg. Then I pulled the rest of the pantyhose all the way up my legs and snugged them up around my waist. It was at that point where the extra factor of having the nylon rub against my penis gave me the most intense feeling I had ever had."

"You came straight away?" Laura asked with a slight grin.

"I think so." Ben answered "I was only young, I must have still been just prior to puberty, and I had no idea what masturbation really was so I hadn't actually cum yet either, so this was probably the feeling of an orgasm without the mess. I lay down on my bed holding the other two pairs, while also rubbing my legs against each other like a cricket, enjoying the sensations for what seemed like hours. Obviously at some point I realized that I needed to get them into the wash with the rest of the clothes or mom would know something was amiss so I got undressed, and put on my regular clothes and then took them down to the laundry room to get the washing going."

"Sounds like you had a memorable time then?" asked Laura, taking another sip..

"Oh yes, it was great, but that was a one off that unfortunately didn't get repeated for a long time as there wasn't the opportunity to be alone with her underwear before the wash, and I didn't want to risk damaging a fresh pair from her room. But, as luck would have it, about six months later we received some junk mail in our mailbox. A pantyhose manufacturer, I think it was Silkies, was trying to drum up business and had distributed a free sample pair to every house in our town. When I collected the mail from our mailbox one day I found myself staring at the package addressed to my mom with the promotional info written all over it. I realized that she would have had no idea this had been delivered, and I could take it without her ever knowing. So that's what I did, and that's how I acquired my first pair of pantyhose."

"Sneaky!" chuckled Laura with a smile "What did you do with them? How did you hide them from your mom?"

"I had a set of drawers where the actual drawer sliders could come out. Under the bottom drawer was a space you could only get to if you took that drawer out. I kept them there. It was a bit of an effort to retrieve them every time but it was worth it. I wore them many times when I was alone, including sleeping in them overnight, and I couldn't get enough of the feeling. That lasted a few months until I finally laddered them to the point where they couldn't be worn anymore. I was quite annoyed, and incredibly frustrated, so I ended up taking the chance of stealing a few of my moms. She had a whole drawer full of them so I don't think she ever noticed."

"Oh she noticed. She just didn't say anything." said Laura, smiling again at Ben's embarrassment.

"You think so?" replied Ben, taking another deep swig of his whisky.

"Definitely. Moms always know." said Laura, knowingly "She would probably have noticed things moved around in her drawers, or maybe you left a drawer slightly open or something. Kids are rarely careful enough to cover their tracks. Neither of mine were."

"You have kids?" Ben asked with a raised eyebrow.

"Two boys, both long since left the nest." replied Laura with a hint of melancholy "But both of them helped themselves to my underwear on a number of occasions. It's only natural for young boys to explore their sexuality and something like their mothers underwear is an easily accessible stand-in for a real woman when one isn't readily available yet. There's probably a lot that Freud could say on the subject too, but they never damaged them or made a mess, so it never really bothered me and they both grew up to be reasonably well adjusted I think." Laura's eyes glazed over as she remembered when her boys were young for a moment. She took another sip of her whisky and returned to the present.

Ben noticed the lack of a ring on her finger and thought now was a reasonable time to ask the question "Is their father still in the picture at all?"

"No" sighed Laura "We split up a few years after the kids left. I managed to get him to wear some lingerie items for me a few times before we divorced, but I don't think it was something he enjoyed as much as I did, and ultimately he decided to trade me in for a much newer model. I haven't been in a significant relationship with anyone since. Just a couple of flings shortly after the divorce. Other than that it's just been me, my expensive lingerie collection, and my Hitachi."

Ben could see the pain in her eyes as she recalled the breakup "That sounds lonely." Ben said quietly, consoling her a little "How long has it been?"

"Too long, Ben, far too long" replied Laura "But hopefully it won't be much longer" she quipped with a cheeky grin "So anyway, enough about me, back to your story. You told me how your appreciation for pantyhose started, but how did you end up getting fully dressed in lingerie?" she asked.

"Well... having a few pairs of pantyhose was nice but as I grew older my awareness of the female form grew too. As a result I became more aware of women's private areas and, more importantly, what covered them. Then, like your boys I guess, I needed to experiment a bit. I took some of my mothers underwear from the back of her drawers so she wouldn't notice, although I see now that she probably did know."

Laura grinned and nodded sagely at Ben.

"First it was just a pair of black full back satin panties, nothing particularly fancy. Those felt wonderful on their own. I used to spend hours just touching myself through them while I lay awake in bed at night. I followed those with a few other pairs that looked like they didn't get worn often to try to limit my risk. Then I got a little braver and tried one of her bras. It was tricky to get on as I couldn't figure out how to do up the hooks at first, and didn't fit well because she was a 36DD which was completely the wrong size for me, but the idea of wearing something all over was still intriguing to me. Then I tried on a few of her foundation items like a girdle, basque, and a corselette. These were great because they were just so snug. It's like an all round hug all the time you are wearing them, and I love them. I have quite a few of them at home now, but ultimately because my mom had so few of those items I couldn't steal them without it being obvious so I mostly kept to just pantyhose for a good while."

"So when did you start buying whole outfits and wearing things at work?" Laura said with a bit of a smirk.

"Honestly, wearing things actually in the open at work like this is new. I only did it tonight because I was reasonably certain I was going to be alone all night." Ben rolled his eyes and chuckled a little at the situation " But buying underwear? I have been doing that for years now. Unfortunately I had to get rid of everything when I went to college as I had no safe way to store them in my dorm room without getting caught, and I didn't want my mom to find them at home either. The whole time I was there I had a constant urge to find some and wear them but never managed to get the opportunity. So when I graduated and I finally got my own place, and some disposable income, I plucked up the courage and went on a bit of a spree. I took all of my measurements and bought several of almost everything in roughly the right sizes, and then fine tuned things that didn't fit well. I think I have managed to get to a point where I know my sizes in women's underwear pretty well, and can buy things off the rack with some confidence."

"That's a really interesting story, Ben." said Laura "Thank you for letting me in on your secret. Have you ever shared your interest with anyone else?"

"No, you are the first." replied Ben candidly "Honestly I was sure you were going to fire me when you saw me like that, and I don't think any of my girlfriends over the years would have reacted any better if I came out to them as a crossdresser."

"You might be surprised how many women would be accepting of your hobby, but if you really think that would be their reaction then shame on them." said Laura as she moved closer to Ben "They will never know the joys of intimacy with a partner when you are both wearing silky lingerie." Laura placed her hand on Ben's slip covered knee. "Would you like to experience those joys, Ben?"

Ben gulped, took a final swig of what remained of his whisky and replied "Definitely!"

Laura leaned in closer and placed a slow, sensual kiss on his lips. Ben leaned into her advance and they embraced for a moment.

"Let me show you how a real woman treats a man who is willing to embrace his feminine side" whispered Laura, as she slowly lowered herself down Ben's body.

She started by placing small kisses all over his upper body and chest. She paid particular attention to the bra, and made sure to allow the material to move across Ben's skin. He reacted with a jolt as the material in the bra cups lightly brushed over his nipples. He hadn't realized they were so sensitive before, but maybe it's a bit like tickling yourself, it's only really effective when someone else does it.

Working her way down his body she kissed across his stomach. She was suitably impressed with how well toned it was. So many of her recent partners had let themselves go and had more than a little extra weight around their middle.

She continued to kiss down his slip covered legs then, when she reached the bottom, she lifted the slip and put her head underneath.

Ben's mind reeled at the thought of a company director currently knelt on the floor in front of him in the middle of his office in matching lingerie with her head up his own slip 'skirt'. It was a situation that he could never have dreamt would happen in a million years, but he was enjoying it immensely.

Laura continued her mission as she kissed her way back up his stocking clad legs making sure to pay even attention to both legs, kissing and licking her way up to her goal. The sensations were something Ben had never felt before and the new experiences were coming thick and fast.

When she reached the top of his stockings, Laura started to lick the exposed skin between the stockings and the panties and this was driving Ben wild too. His cock was now rock hard and causing the panties and slip to stand up like a tent with his engorged 6 inch pole in the middle.

Laura slid her hands slowly up Ben's nylon encased legs as she reached for his panty encased member and guided the tip of it into her mouth still wrapped in the material. She moved her head up and down slowly, taking more and more of his manhood into her mouth each time, whilst simultaneously causing the panties to rub back and forth against the head.

"Oh god that's amazing" moaned Ben "keep going, but I'm not going to last much longer if it gets any more intense."

Taking the hint, Laura backed off a little and decided on a new approach. She moved his cock down and fished it out through the leg hole in the panties. This gave her full access to the entire area from his tip to his asshole. With the newfound access she moved down and started to circle her tongue around his rosebud, lightly pressing the tip into his hole.

Ben had never really considered anal play at all, but the feelings he was getting from her probing were making him realize it was something he wanted to explore further.

Laura then slowly started working her way up past his perineum licking and kissing every inch. Then she got to his balls and slowly sucked each one into her mouth and gently licked all around them like ever-lasting gobstoppers. Ben was in heaven. Finally she gave a slow but strong lick all the way up to the tip of his cock and then engulfed the head with her mouth.

Ben was grasping at the arms and back of the sofa to try and hold back his orgasm and make it last. He was almost there.

Laura started to bob her head up and down on his shaft, varying her speed and licking underside of his head with her tongue. Then without warning she pushed her head down harder than before and took his entire length deep into her throat. This was all Ben could take.

"Laura, I... I... I'm about... to... cum!" he stammered, still trying to hold back. Laura responded by grabbing the back of Ben's thighs and forcing his cock even further down her throat. That was it. Ben started to shoot his cum into her mouth harder than he had cum for a long time. Spurt after spurt of semen flooded down Laura's throat and she swallowed everything.

She backed off a little as his pulses slowed down and she started to suck harder to ensure she got every last drop he had. Finally she started to lick around the tip until he couldn't take it anymore.

"Stop... stop... that... was... amazing!" Ben begged and then sighed as he slumped back onto the sofa. "I hope you realize I am now going to have to return the favor?"

"I was counting on it!" said Laura, as she lifted her head out from under his slip and fired the same cheeky grin she used earlier at him. "Now come here!"

Laura grabbed his hand, pulling him upright again and embraced him with a deep French kiss. Her tongue had a slightly musky and salty taste, and he realized he was tasting the remains of his own emissions in her mouth. He had never tasted his own product before and while it wasn't something he expected, there were many unexpected things happening tonight, and he didn't hate the taste either.

Ben helped Laura up off of the floor in front of him, on to the sofa, where they continued to make out for several minutes. His hands started to explore her body some more, softly caressing her voluminous chest, lightly sliding his hand down and tickling the skin as he made his way to her hips. He pulled her in tightly, lifting one leg over his slightly to give him better access to her butt. Ben then slowly ran his hand down over her butt cheek, caressing her body through the amazingly soft satin material of the slip that encompassed her lower half.

Laura briefly broke off the kissing "Mmm that's wonderful, don't stop." she said, before resuming her attack on his mouth, face, and neck.

Ben continued slipping his hand gently over the silky material up and down her thighs, occasionally tickling, softly rubbing the muscles in her legs until he reached the hem of the slip. His hand moved to the soft nylon encasing her legs, but kept going until he reached the stiletto heels.

He didn't have a shoe fetish (probably one of the few fetishes he didn't have) but he was a lover of all things feminine, and he appreciated a sexy looking shoe when he saw one. He mostly appreciated the foot, leg, and thigh attached to it though, especially if they were covered in silk, or nylon.

Ben turned and knelt between Laura's legs, pulling her slip up to her thighs so he could get closer to her face to face. He gave her a deep and passionate kiss and then proceeded to work his way down her body.

He started the same way she had by nibbling and licking her neck and collar bone. His hands gently toyed with the straps on her bra from behind while pulling her body towards him. Slowly he kissed and licked his way down her upper chest and then detoured off to the side nuzzling his nose into her armpit.

Ben inhaled deeply "What are you doing?" said Laura, a little embarrassed despite her current situation "I'm all sweaty there."