The Pinup Vs the Vet

It was time for the annual fundraising drive put on by the local organization that supports veterans. Erica Smith always made sure to volunteer or help however she could since veterans were so near and dear to her heart. Erica grew up in a family of patriots who loved to serve their country. Being raised by two parents who both served in the military made her dedicated to serving those who had served themselves.

Erica was cursing herself for running late as usual but this time she had a valid excuse. Her hair appointment was delayed because her usual stylist was out sick, so she had to use the only stylist who was free. Erica had seen this stylist before but never used her. She was quite older than the rest of the stylist in the salon, but Erica did not have time to be picky today.

Turns out the woman's name was Gladys and being that she was in her late 60's, she was limited on her knowledge of modern hairstyles. She convinced Erica to try something new and let her work her magic on Erica's beautiful hair. Erica was doubtful but she was also confident that she could pull off any look.

For a housewife in her low-30's, Erica was an absolute bombshell. Standing at 5 foot 9 inches, Erica was a classically beautiful woman with long brunette hair. She had legs that went on for days, a round juicy booty, large and firm C cup breasts, and eyes that could seduce any man that ever crossed her path.

Erica had her fun back in her 20s with seducing men and using them to get what she wanted without hardly ever giving them anything they wanted in return. She always thought that one day this would catch up to her but so far, her luck had not run out. She did eventually get bored with using men, and sometimes women, as play toys and she eventually settled down with her husband Tim.

Tim was a good-looking man that provided for Erica's every need. She provided for him with children and as a pleasant bonus she was the eye candy trophy wife that he always dreamed of. Erica made sure to keep her eye candy status by working her ass off to keep her figure after both children burst on to the scene. She was very proud of how she managed to do this and was getting aroused thinking of her own figure when Gladys' voice woke her up from her daydream.

"What do you think of it Honey"? Gladys asked for the third time while wondering what this woman could possibly be thinking of. Erica snapped to attention and turned to look in the mirror that Gladys had provided. The hairstyle was what Erica would have described as vintage and gave her vibes of the golden age of Hollywood. She had lots of bouncy curls and she had the distinct feeling that she resembled what you would call a classic pin up girl. Erica loved the look since so much of her family was involved in the military and she thanked Gladys for her work and quickly left to get to the volunteer organization meeting.

Gerry was getting impatient and starting to wonder if the last volunteer assigned to his team would ever arrive. He had already assigned the rest of his volunteers to their tasks and he was starting to think of what fun he could get into by the end of the fundraising week. Generally, there were all sorts of events and parties that he could prowl while looking for women to seduce. Having been in the Vietnam war himself, he was passionate about the purpose of the organization, but he was also gifted with an appreciation for life that made him fully value every day he had on this Earth. Surviving a brutal war will have that effect on you.

Gerry was what you would commonly call a silver fox. Being in his upper 60s he could easily pass for a man in his low-50s or possibly late 40s on a good day. He kept in shape but doing his usual boxing workouts and made sure to keep up with his internal and external wellbeing. He stood at 6 foot 4 inches, had a full head of white hair, great muscle tone for his age, and a chiseled jaw that could make any woman faint that crossed his path.

Gerry had no problem with the ladies and was caught up in a daydream of chasing skirts when a soft-spoken voice interrupted his playboy thoughts.

"Hello Sir is your name Gerry and are you in charge here"? Gerry turned to see a beautiful tall woman that almost took his breath away.

"Why yes I am Gerry" he said. "And what might your name be"? The model looking woman said that her name was Erica Smith and that she was very sorry for running late. She hoped that she was not too late and that there was still something that she could do to help during the fundraising week. Gerry could not help but smirk and laugh on the inside as he thought of how lucky he was to have this gorgeous woman fall right into his lap.

"Yes, Erica it is a pleasure to meet you and I am sure there is someway we can get you to perform and serve a purpose".

Erica was relieved to hear this. With her husband out of town for work with his secretary (as usual) and the kids off to summer camp, Erica needed something to occupy her time besides working out.

Gerry had a rough outline of what he wanted to do but he needed more time to set up his trap. "Tell you what", says Gerry. "We have done most of what we can here today, you should come to my office in a few days and I will set you up with something you can do that will be a big help". "I will send you further instructions later tonight so that you can prepare for the function."

"That sounds great" said Erica and she turned to walk out of the office relived that she had not missed her chance to volunteer.

As Gerry watched her walk away, he couldn't help but feel like a hunter watching its prey walk right into his scope.

Gerry raced back to his home office and began converting it into a photography studio. The space was essentially his garage that stored a few odds and ends from his war memorabilia. Seeing Erica's hairstyle and hourglass figure had given him the idea to create his own pin up calendar. Erica would be his very first model and if his plan actually worked out, he could serve his needs, and make some money for the volunteer organization.

Gerry had luckily dabbled in some amateur photography back in the day and kept up with the hobby, so he had all the necessary camera equipment. He just had to set up his office, find something exotic for Erica to wear, and finally convince her to pose for him (amongst other things). Setting up the office would be easy. He just needed to move around a few items and set the stage for something worthy of a classic pin up scene.

He decided to do a military inspired pin up theme since the week's events were meant to benefit veterans. That plus he had plenty of memorabilia from the Vietnam war being that he served in it and was a history buff himself. Gerry had some authentic items from the time period along with some props that would work quite well including his vintage motorcycle and some old uniforms including helmets, boots, belts, etc.

As far as what he wanted Mrs. Smith to wear, that would be a more challenging but exciting endeavor. Gerry had a few articles of women's clothing laying around from past female callers, but he would need to find something more appropriate for Mrs. Smith to wear. He figured a typical GI women's dress would be great with some stockings and high heels. Gerry did not know her exact measurements, but he had eye humped enough MILFs in his day to guestimate her sizes. For a man his age, Gerry was quite adequate at using the internet, so he ordered the clothing online and made sure to select next day shipping. Finally, Gerry had to begin to seduce and convince his model to bear all for the camera. Using the volunteer organization's sign-up sheet, he contacted Erica via email and sent her instructions on what she needed to do next.

Erica was at home sunning herself by the pool when she got an email notification on her phone. It was from the nice gentlemen she had met earlier that afternoon. She thought to herself that he was a rather good-looking man for his age. She would have guessed that he was at least in his early 50s maybe older depending on how well he kept up himself. If he were in his 60s, that would have made him double Erica's age but that still didn't stop her from feeling a mild attraction to the older man.

It was at this moment that she noticed she had been mindlessly rubbing herself while thinking all of this. It was an easy thing to do at the moment since she was tanning herself in the nude and she had not seen her husband since last week. She knew he would be back by the weekend but did not think she could wait that long for some sexual release.

It was just as well anyway. Her husband was a good lover, but she could do the job quicker herself or even better yet with the aide of one of her nightside companions. She had a few different kinds, but her favorite was her rabbit vibrator. It was one of the luxury models, what could she say, she liked the finer things in life. Her husband loved to watch her use any of her toys and he even purchased some for her to try. Tim, her husband, had recently gotten into the idea of her using a huge dildo that could really stretch her open. He purchased her a few different sized dildos. One that was pretty average sized, one that was above average, and finally one that was what she would call a monster dildo.

The monster dildo looked to be at least a foot long and probably 3 to 4 inches thick. It was molded after a famous porn star from the 70s and she had a hard time believing that anyone could be that well-endowed, but she wasn't much of a porn fan to know. She told Tim that she was as adventurous as the next girl but that she would have to warm up to the idea of having that monster cock inside of her.

Even though she could be a bit of a tease, Erica always thought of herself as the shy, timid girl next door type. She worried her husband may see her in a different light if she had too much fun with these toys but there was nothing stopping her from having fun while he was gone. She had no problem using the average size dildo and she had just recently mastered the above average size. Maybe today was the day she tried the monster dildo, but she was still a limit timid at the thought of trying it. Her biggest fear was that she would actually love it and lose interest in her husband, but that thought was silly she told herself.

Erica turned over in her lounge chair to rest on her stomach and raised her feet up over her butt. She began to read Gerry's email and was finding his idea very exciting. Gerry had the idea to sell a pin up calendar inspired by the military and use the proceeds to benefit veterans. The photos would be tasteful but would also need to be sexy so that someone would actually purchase it.

Erica had thought of making a career of modeling in the past, but she found it easier and less work to just let men buy her gifts and pamper her. She had a few sugar daddies in her past that she would tease with sexy photos and even did a few glamour shoots but that was as far as she got with modeling.

Gerry's email told her that everything should be in place in a few days and to meet him then at his private studio. Erica told Gerry that she loved the idea and looked forward to it. They exchanged phone numbers and kept in contact over the next few days. They mostly made small talk, but Gerry was sure to be flirtatious and started to plant seeds in Erica's mind that he hoped he could harvest. Erica slowly found herself slowing liking the older man more and more and soon she began to trust him. Which is exactly what Gerry needed from her.

Finally, the day of the photoshoot had arrived. Gerry could barely contain himself. He had refrained from having sex with other women or even masturbating just in hopes in saving up a large load for this MILF with the dynamite body. The added bonus of this was the longer he withheld, the more ravenousness he would be in bed with her if he got his way.

Erica herself, had gone without any sexual relief but Erica's was not intentional and had no motive behind it like Gerry. She was just too busy with her usual duties and activities that kept her busy as a housewife. Little did she know that this would be a part of her pleasurable but intense downfall.

Erica knew she would be wearing something skimpy eventually, but she saw no need in dressing that way on the way to the photoshoot. She dressed in a modest mommy outfit of yoga pants and a loose t-shirt with some sneakers. Gerry had done an excellent job of guessing her clothing sizes and she helped fill in the gaps where he needed help. She was so surprised with how close that he got that she almost questioned it but thought he was probably just good at it from being a photographer. Gerry had told her he loved her hair and that was his big inspiration for the calendar, so she did her best to preserve the curls that Gladys had given her earlier in the week.

She arrived at the address Gerry had provided and she was surprised to find out that the studio was in his house. It was a lovely home and almost as large and nice as Erica and Tim's. Erica walked to the front door and rang the doorbell. A well-dressed man soon greeted her at the door, and she acknowledged to herself that he was even better looking than she remembered.

Gerry thought the same to himself of Erica and gave her a body a good scanning from head to toe. He gave Erica a brief tour of his home, mostly so he could show off, and show her his awards, trophies, and medals he had earned from across his life including his time in the military.

Erica was very impressed and found herself getting a little flustered from Gerry's seemingly harmless flirting and playful boasting. The tour proceeded to the bar where Gerry made Erica some of the best old-fashioned cocktails she had ever had. She could definitely hold down her whiskey but after 2 drinks, even she was starting to feel the effects.

Gerry was impressed that a woman of her size could drink two cocktails that were mostly whiskey in such a short manner, but he decided to cut her off just so that she was fully aware of what was going on and nothing potentially illegal happened.

The tour concluded at Gerry's photography studio where Erica was greatly impressed with the setup. It almost looked like a scene from the set of the MASH tv show. There was a retro motorcycle from the 60s, an old timey tent with a full-sized desk inside, a smallish replica of a jeep that would have been used during that time period and a few other knicks and knacks.

Gerry told Erica that her wardrobe would be inside the tent and that she could change there in privacy.

Erica told Gerry how impressed and excited she was and off she went to change into her attire.

Gerry echoed back how excited he was while subconsciously rubbing his already forming hard on from the outside of his pants.

Erica stepped inside the tent and Gerry stepped back into the bar area to get a peak on his security cameras. Erica removed her yoga pants and exposed her itsy-bitsy G-string that barely did much concealing. Gerry almost fainted at the sight and couldn't wait to see that ass bouncing on his big cock.

Inside the Tent, Erica surprised herself with how fast she had undressed in this stranger's house. At this point, they had been speaking for a few days so maybe she didn't see him as a stranger anymore, just an old friend. A much older but sexy friend.

As Erica's mind continued to race, she took in the full picture of the outfit that Gerry had laid out for her. It was a female version of the brown private's uniform with a few medals and bars attached to the dress. There were tan tights and some silver strappy high heels. Finally, there was a cute little brown cap to top off the uniform.

Erica was immediately worried that in the high heels and with the dress being so short, that her apple bottom booty would peek out from under the dress. She hoped the pictures would be from the front so that she wouldn't worry about being too cheeky, she isn't British, but the word was just too perfect not to use. Erica reluctantly started to put on the costume but the combination of the alcohol and her satisfaction of doing a good deed started to ease her doubts.

The dress fit her body like a glove. Gerry had done a masterful job of sizing up her body. The dress was just the right amount of low cut to show off the girls but not too revealing to seem too trashy. Her modest C cups really looked to be spilling out of the dress but also where held in place firmly to where she thought there was no chance of a wardrobe malfunction. They would have to be pulled out she laughed to herself thinking of what a good visual it would be but thinking thank goodness her husband was not there to see this.

He knew she could be wild in private, but he knew very little of her sugar daddy days back in college. After squeezing into the rest of the outfit, Erica stood back and admired her beauty in the full-length mirror that was in the army tent. She was still just as gorgeous as ever even after having two children. Her new hairstyle matched the pin up vibe perfectly and she knew the calendar would be a success especially if the other month's models looked as good as she does. With the heels on, Erica was now well over six feet tall and the tights evened her legs out and made them even more a vision. The last step was to go out and show Gerry how she looked and hope he approved but deep down she knew he would.

Gerry saw that Erica was almost done and he hurriedly walked back into the studio. "How do I look", Erica shyly asked as Gerry took in the full view of the amazon warrior in front of him.

"Like a model picked right from the pages of the most timeless and graceful magazines" Gerry replied.

Erica tried not to blush, but she felt her body betray her for the first of what would be many times that evening. "We should start off slowly and get some natural shots with no props to get you warmed up" Gerry suggested.

Erica liked the idea of starting slowly and readily agreed. As they began, Gerry made sure to compliment Erica and shower her with the attention he hoped she wasn't getting at home. Her told her she was a natural, how she should do this professionally, how it was amazing she was for doing this and how much he was sure it would help out the veteran organization, and even more flattering things that continued to stroke her ego. Erica was eating up the attention and started to get slightly aroused if she was honest with herself. She didn't know if she could cheat on her husband, but he did spend an awful lot of time with his young secretary these days.

"Ok next we will get some shots of you on the motorcycle" stated Gerry as Erica awoke from her naughty thoughts. Erica loved motorcycles and thought they were sexy, so she was more than ready for this. She could feel herself starting to get into the sexiness of the experience and was starting to lose herself in the moment.

Gerry could pick up on this and almost smelled it like blood in the water. He decided to hasten his plan. "I have just had a great idea Erica". "I've got a similar uniform that matches yours and I could change into it and be some eye candy for the female consumer". "That way we can double our sales".

Erica thought it was a great idea and thought she would feel a little less exposed if there was someone posing with her. Gerry ran off to change and quickly returned in a brown private's uniform that matched hers. It was nothing too crazy, but it was unbuttoned in the front to show off some of his abs and the shorts rode up high enough to show off some man thigh and perhaps some crotch action if Gerry was packing. Little did Erica know that he was packing more man-meat then she had ever had in her lifetime.

Gerry setup his camera on a timer and started suggesting poses that the two of them could take together. At first, he left plenty of space between the two but after a few minutes, he started suggesting more poses that were a lot more intimate. Soon they were embracing, holding each other, touching how lovers would, staring into each other's eyes, the whole nine yards.