The Insurance Salesman Ch. 01

"The Jamming of Jessica"

I have been selling insurance for many years, and like many sales jobs it is not much more than making tons of phone calls and lots of driving. You get to meet many people with a variety of lifestyles with many eccentricities. Sometimes you have to go with the flow when doing sales in the hopes of getting them to buy your product. I admit that I have on occasion used tactics I am not too proud of the get the job done. For the most part though it is like anything else, you do what you have to do in order to survive.

I have been trying to keep this one appointment for several weeks, but for various reasons we have had to reschedule many times. Jessica was a single mom in her mid twenties with a young boy who was eight years old. I have discerned from our many phone calls that she makes good money running her own business, however like most self employed people needs family coverage. Finally it looks like this week we will be able to keep our appointment. I too work mostly from home as does Jessica, she does have an office she said that she occasionally uses when she has to. This is where we plan on meeting in order for me to do my presentation of polices we carry.

Now I must give you a little background on me. I am in my mid thirties, and no children, not that I didn't want them. My ex-wife finally explained that she didn't want children and that is why she is now my "ex-wife". We had our good times, and enjoyed a few mutual fetishes. One of which is my obsession for wearing pantyhose. I realized when I was younger about my fetish during the Halloween season. I have three older sisters who liked to pick on their younger brother. This one year they all decided they would all dress up as cheerleaders, and thought it would be funny that I join them. I was around ten and my oldest sister was around eighteen when this costume party was setup. They figured it would get a big laugh when everyone finally realized who the "little princess" was. They went all out with this dress up plan, and since two of my sisters were in fact cheerleaders they had plenty of uniforms.

At that young age it wasn't unordinary to see my sisters get changed or even take a shower. With mom working so much and dad passing away when I was about two, my sisters use to help with taking care of me. This included among others, bathing when I was smaller and teaching me how to get dressed. I even on occasion would help them get dressed for dates or dances, and even parties. Since this was basically a house full of women, having pantyhose all over the place was pretty normal. I was helping them get things together for the costumes and trying to figure out what they were going to put me in. I was growing pretty good and everyone figured I would end up as the tall strong man I now am. I am 6' 3" tall somewhat muscular, but with a bit of a pooch, too much beer on the weekends I guess.

Now back to today, I learned early in this business that you have to dress to impress. So I do my best with dressing up. I have many suits, shoes, ties, cufflinks, shirts..Etc. I also wear pantyhose every day under my suits, mostly black because I can pass it off as wearing silky dress socks. However today I was wearing my chocolate brown pinstripe with a pink shirt and pink striped tie. I wore tan pantyhose that day because I wore my dress boots. They are really not full boots, but rather like a high top sneaker as they come just a bit over the ankle. The other thing I like about the pantyhose goes back to that day of dressing up with my sisters. On occasion I would wear some boxer shorts and would sometimes feel uncomfortable when my penis would not stay in place. Depending on how I was sitting or standing you could tell quite clearly how big I was, and this wasn't what I wanted to broadcast.

I was about fifteen minutes early to my appointment with Jessica at her office. This was pretty much just another small space similar to a condo the way it was setup. What could be a small living room was used as a greeting area, with a small dinette area off to one side. Down a short hallway were two other rooms she used as offices. Out in the greeting area she had a few small couches and tables for people to be comfortable while they waited. Being tall like me they were a bit low for my tastes, but like I said you have to do whatever to get the sale. And my comfort wasn't always a top priority. As I walked in and looked around I heard a voice say "be right there", I guess she has a door sensor or possibly a camera to see if anyone is out here. I sat down and waited patiently for a few minutes and started skimming through a magazine on the table. A few minutes go by and not paying too much attention I just kind of got a bit too comfortable. I leaned back on the small couch crossing my legs while perusing this magazine. Shorty after I heard the click clack of high heels walking down the hall so I looked up from the magazine and Jessica walked into the room.

I was pleasantly surprised at this mid twenties stunner standing before me. She gave me the quick once over as I did to her. As I was leaning forward to get up from the small short couch my pant legs of my suit were pulling up as they tend to do when getting up from a sofa or chair. What I hadn't noticed is her eyes wander up and down me while I was standing up. What I did notice is was this statuesque woman standing in front of me. From the way I had to get up I enjoyed the view all the way up from her feet to her face. She had on the perfectly shined black strappy open toed pumps, which accentuated her much toned legs. Of course I immediately noticed she was wearing very sexy and seemingly expensive pantyhose of a nude or barely tan color. The next thing I noticed was the navy pinstriped pleaded skirt that fell about four inches above the knee, followed by a medium blue silk blouse covering up a very ample pair of breasts. She had this amazing gold necklace with various pendants hanging from it that matched her bracelets and earrings. She has this amazing smile surrounded by the gorgeous pouty full lips covered in luscious red lipstick. I then looked into her beautiful hazel eyes and we introduced each other.

As we were speaking to each other I glanced at her flowing auburn hair that fell just above her shoulders. She wore it with a bit of flair as well, sort of a layered look with very slight curls. All in all this was a very beautiful and stunning young woman. She noticed how enamored I was with her beauty and just gave a little smile to acknowledge my ogling. We chit chatted a bit right there and then she asked me to follow her down the hall to her office. She immediately made a quick spin around and started walking toward the hall and that is when I noticed how light and loose fitting her skirt was. As she spun around it lifted a bit and showed a little bit of her long toned legs. She has wonderfully shapely thighs, the best I have seen in some time. She walked away with that little strut women do to get us guys to follow them.

She walked into her office and asked me to sit down in front of her desk as she walked to the other side. Now her desk was a bit different, a glass top with metal legs with some small computer shelves below it. As she sat down at her chair she gave me a little peep of her legs as she spun to sit facing me. I felt myself getting aroused a bit, but tried not to show it if I could. I started to go over our policies and what not which can take some time depending on how many questions people have. Jessica seemed to have many questions and I did my very best to explain completely. As we went back and forth through the presentation I would notice her trying to distract me from my work. Jessica would often cross her legs back and forth with a little leg spread while doing so. She would dangle her shoes almost the entire time we were sitting there. I would scoot up in my chair at times and then slide back and as I did I wouldn't realize I was showing a little leg myself. Being that I wore pantyhose myself every day I would usually forget I was wearing them. I managed to finish my pitch and she decides to buy a few different policies from me.

After taking care of the paperwork we chit chatted a bit and both seemed to lean in closer to each other at the desk. We both actually had to pull our chairs closer to the desk and as we did she crossed her legs again. And while she did she bumped my leg just above my ankle boots. That is when I realized I had on my own pair of sexy pantyhose under my pants. As she did she looked down at my feet and apologized for bumping into me. I told her to forget about it, but she kept looking down at my feet. I asked her if she like my shoes and pushed my foot a little closer to her to get a better look.

She smiled at me and said, "Actually it is not your shoes I liked, it is what is just above them".

I blushed as I tried to respond, but she beat me to it. She dangled her shoes and then kicked it off her foot. She then stuck her pantyhosed covered foot up under my pant leg and rubbed my silky shin.

"I thought so," she said smiling at me, "You're wearing nylons, right?" she asked excitedly.

"NO, actually I am wearing pantyhose" I said to her smiling back at her, "Why?" I asked in return.

"So EVERYTHING is covered? All the way up to your waist?" she asked with a huge smile and wide open eyes staring at me. "I have to know why you are wearing pantyhose. You have to tell me." She demanded.

So I obliged her and told her the Halloween story, but left out the part about my penis. It was a little weird talking about private parts to someone new, even if you want to fuck her brains out.

"I have heard of men wearing women's clothing, but never seen one actually do it" Jessica said snickering. "Are you gay? Or bi-sexual?" she said inquisitively.

"Absolutely Not" I exclaimed back to her.

She apologized and explained that she was just curious as she noticed I didn't wear a wedding ring. I chuckled and then explained that I was divorced and how she shared a passion of pantyhose. And that the reason we got divorced is because she didn't want children and I did. A bit shocked she leaned forward in her chair and uncrossed her legs placing both feet on the floor.

"You are kidding me." she exclaimed while she slightly opened her legs without realizing. "That is exactly why I got a divorce. When my ex found out I was pregnant he freaked out and took off." She explained emphatically.

As she was doing this I couldn't help but look down through the glass table top at her stunning legs which now showed a bit more of her upper thighs.

"Stockings or Pantyhose?" I asked as I looked back up at her smiling.

Blushing she looked back at me and said, "Pantyhose of course, silly. I don't like stockings they never stay up and you can see the garter clips most of the time".

We both quickly ask the same question at the same time, "Panties or bare?" We started giggling loudly at the same time.

What she did next shocked me, as she reached down under the glass table and lifted the front of her skirt all the way up and exposed her nylon covered bare pussy. She was very well trimmed with just a small patch of hair above her lips.

Blushing and staring a bit I said, "Well I guess that answers that question..... Thank you for that." Smiling and wide eyed the whole time.

She took her time lowering her skirt allowing me to soak up the view, which I honestly could not take my eyes off of.

"Well silly boy, how about you? Are you going to answer me? Are you going to show me what is under your pantyhose?" She said seductively with a sly little grin on her face.

I explained how it wasn't as easy for me to just lift a skirt to show what I had on. I have a bit more to do in order to show my pantyhose to her. Being brave I told her that I may need a little help to show her.

Smiling greedily she got up from her seat and started around the table towards me as I stood from my chair. I had already had my suit jacket off and hanging on the back of the chair. She seductively walked up to me and reached for my cock through my pants.

Jessica got this big grin on her face and looked up at me, "Is that a rabbit in your pants or are you just REALLY happy to see me?" She said smiling greedily at me.

Rapidly she started to unbutton my pants to see what was going on in there. I quickly kicked off my shoes and then my pants fell quickly to the floor. She stepped back a few steps to take a good long look at my cock restrained behind my pantyhose.

"I see there is another reason you wear pantyhose, that thing would show itself under any pants you wore." She said staring in amazement.

Reaching down and fully removed my pants I neatly hung them over my coat to not damage them. She was still staring when she asked how big it really is.

I told her that the pantyhose do help conceal its size and that mostly I do wear a control top for these purposes. She walked back near me and started rubbing her hand all over my swelling cock. As she continued to rub my cock, I reached behind her to undo her skirt and let it fall to the floor. We mutually caressed each other's hose covered bodies. Even though I was wearing control top pantyhose my cock was still showing a decent size. I encouraged her braveness even more by pulling down the front of my pantyhose releasing my entire cock for her viewing. By now it was almost fully erect and she kept rubbing and caressing it until it was hard as stone. Then she had knelt down in front of me and had to start using two hands to stoke my cock.

She continued to have this look of amazement on her face when she exclaimed "I have never seen a cock this big in my life. I mean I have seen some on video, but never this close."

She demanded I tell her exactly how big it was and I explained I haven't measured it in some time but I believe it is around nine inches.

She leaned her head forward and tried to use her head as a comparison, when she realized it was futile at best. She leaned over to a cabinet and grabbed a ruler and began to measure my cock. She placed the ruler under my cock and pushed back until it stopped.

Looking down at the ruler she shouted. "Oh my God, this monster is just over ten inches".

I guess I forgot that if you measure from the underside it gains a little length, but I wasn't about to tell her that. She immediately wrapped her luscious lips around my swollen cock, giving it her best effort. With a mild moan I commended her on her skill with sucking cock. I grabbed her gorgeous auburn hair and began pulling her head closer to me pushing my cock as far down her throat as I could. Almost gagging she managed to get three quarters of my cock down her gullet. Now holding her head with both of my hands I began to face fuck her with my massive cock, which she seemed to love. She began squeezing my balls and massaging them vigorously while I face fucked her. This continued for around five minutes or so and I was getting close to climax, being that I haven't had sex for some time now. I pulled out to where just the head of my cock was still in her mouth and with a few more hard squeezes of my cock I exploded into her wet mouth. Stream after stream unloaded into her mouth and without any hesitation or signs of gagging she swallowed every drop of my cum without any interruption.

Starting to soften a bit she finished cleaning my cock of all signs of abuse, slurping at times getting every last drop of saliva and cum into her mouth. She stood up and finished licking her lips to clean her face when I leaned down to kiss her. Thanking her for her awesome service I pushed her back towards the desk. Lifting her up on the edge of the glass top desk, I then knelt down in front of her and started to lick her legs and inner thighs. Spreading her legs a bit I found my way to her very moist pussy and gently licked her clit through her sheer and silky pantyhose. The tenderness of her clit combined with the silky sensations of the pantyhose covering her clit. Jessica began to squirm and moan with enjoyment as I continued to tease and lick her clit and sucking on her lips. Her pantyhose where getting soaking wet from my efforts and she continued to moan and even occasionally scream with enjoyment. I ripped a hole in her nylons to release her dripping cunt and get better access to my work. I reengaged her clit with my tongue and mouth continuing a hard licking and sucking action. Soon after this sent her over the edge when she let out a loud scream of ecstasy and started to cum heavily into my mouth and on my lower jaw.

I continued sucking and licking her cunt while she climaxed, pushing her further over the edge. She kept on screaming and moaning with abandon. I leaned back on my knees and let her legs rest on my shoulders until she came back down to earth. Slightly massaging her legs for a short time she looked into my eyes and returned the thanks I gave her not that long before.

Smiling at me she asked. "I wish we could do more? That was awesome, we should meet later so I could feel that monster inside my pussy."

"Why wait?" I said smirking at her seductively.

Confused she looked at me and asked curiously, "You just came so much and so hard a few minutes ago, can you get hard again this soon? Don't you need some rest? I know some men need to recuperate for some time after cumming so much."

Standing up in front of her with a three quarter erect cock I asked. "Does this answer your question?" Walking closer to her as I spoke.

With amazement she reached down and grabbed my mostly swollen cock with her hands and began to stoke it. After a short time it was rock solid once again.

"Be careful with that thing, you know what happens when you get a cock hard again immediately after it cums, right?" I asked her with a wicked grin on my flushed face.

"And what is that?" She asked very seductively and greedily.

"It usually takes a long time for me to cum again. Do you think you can handle that? I mean, you will probably be a bit sore and worn out for a bit after I Fuck the hell out of you."

"Well I will just have to give it the ole American best effort." She stated very eagerly staring into my eyes.

I then pushed her back against her desk, and lifted her petite round ass up onto the desk top. She instinctively leaned back slightly and spread her legs for easy access. I grabbed her below each knee to help support her and keep her legs wide. By now I was once again fully erect and my cock was aiming directly at her very wet cunt. With one of her hands she grabbed my cock to make sure it keeps its aim into her pussy. I slowly pushed forward forcing the head of my cock into her hot wet pussy. As I pushed the entire length of my cock into her, Jessica screamed.

"That feels so wonderful, push that huge cock into my tight pussy. I want to feel you stretch my tight pussy with that monster shaft of yours."

I pushed into her wet pussy until I was balls deep and could not believe she could take my entire cock into her pussy.

"Oh My God, your tight pussy feels so incredible swallowing my big dick."

I began picking up my pace of my thrusts into her pussy. Jessica continued to moan and scream in ecstasy enjoying the pleasure I was giving her. We stayed in that position for several minutes as I continued to pump her pussy with my massive tool. I soon after pulled out and turned her around so she was standing and bent down over her desk. I immediately shoved my big stick back into her dripping cunt. I grabbed her hips and started to pound the shit out of this smoking hot girl until she couldn't take it. She could not believe the intensity of this experience.

"I have never been fucked by a cock this big before." She stated breathlessly.

This was the most cardio exercise I have had in around a month. Luckily I was still in decent enough shape to continue. After about fifteen minutes she noticed I was getting somewhat winded so she pushed me back onto my chair and straddled me. She started to do her own cardio workout on my cock. Lucky for her she was able to have a good range of motion because of wearing such a high heel shoe. I leaned back and rested my hands on her sides trying to keep her steady as she rode my meat pole steadily. We changed positions several times taking turns doing the work. At one point I started to finger her asshole and she seemed open to the idea of anal sex.