She Liked The Idea Of Rounds

The hostess led Frank to a secluded spot on the restaurants outdoor patio.

Frank was: a widower, in his early fifties, he was five ten, had a rectangular shaped face, dark brown eyes, his dark hair was turning gray, he recently started to wear glasses, he was in shape, was clean shaven, and was well groomed. He was wearing: a brand new casual red button shirt with a blue sail boat pattern, black colored cargo shorts, and light blue shoes. He wore this shirt so Poppy could easily spot him.

The hostess: set down two glasses of water, took his order for an iced tea, and left him two menu's. This isolated spot allowed him to view the parking lot and if they discussed sex nobody would hear them. The least thing he wanted was for someone he knew to hear them. He didn't want anyone (stranger or friend) to have a low opinion of Poppy. More important, Frank believed sitting outside would be more relaxing; living in Minnesota good days in the middle of June were coveted.

Frank texted Poppy letting her know where he was sitting. The waitress brought out his drink and asked if he wanted anything. He glanced at his watch and told her to come back in about fifteen minutes. She agreed and left. Poppy answered Franks text with a simple, "I'll look for you."

Even after: receiving this text, many email exchanges, and talking to her on the phone he was concerned this was a scam. He was prepared for Poppy to never show up, give him a call with some excuse, and in a few days request money. With all the spam email he received it was easy to believe this was a scam. Another reason he believed this might be a scam was the woman claiming to be Poppy, never divulged the name of the community she grew up in. All she would tell him, she grew up in Northern England. With how popular the name Poppy was in England it was difficult for him to research her story. The other reason he doubted she was real, Poppy was only the third real women in the last five years who actually responded to his ad. She would be the second woman he would actually meet. What made women reluctant to respond to his ad: he made it clear this was not to be a sugar daddy arrangement, he was no longer interested in getting married, would only be with a single women, and he openly admitted his cock was four and half inches when erect.

The two other women who responded to his ad were surprised he turned them down. The woman he only talked to on the phone, was clearly a horrible match; he politely refused her offer. The woman he met turned out to be married. She believed if they met he would change his mind and sleep with her. It was difficult to turn down this attractive brunette. He just could not bring himself to have sex with a woman who was married; even if her husband confirmed they were in an open marriage.

This strong disdain he had to sleeping with a married woman came from the fact he truly loved his wife of twenty-three years. The only reason he was looking for a friend with benefits was his wife passed away when he was forty-four. The love he felt for her was so strong he felt he could never marry anyone else. Even though he felt this way, he missed having sex with someone else. He was the type of man: who disliked strip clubs, would never hire an escort, and would never have a one night stand. He believed a friend with benefits would be a good compromise.

A part of himself wanted this to be a scam. Frank was nervous. If things went well, Poppy would be the second person he ever slept with. He worried his daughters would find out and disapprove. He was certain they wouldn't like how much younger Poppy was. He strongly believed his oldest, who just turned thirty-one, would never approve of him sleeping with a woman who was thirty-six. He strongly believed his oldest would be disappointed in him. His middle daughter was in her upper twenties. She had a family of her own, he believed she would wonder what he was doing. The only one who might have supported this type of relationship was his youngest daughter; who just graduated college. All three of his daughters were encouraging him to seek out a serious relationship. His oldest tried setting him up with a woman she knew from her church. What they didn't understand, was how deep his connection to wife was, and how strong his sexual desires were.

He was ready to call over the waitress and just order for himself. This is when he spotted a brand new dark blue Range Rover Sport Edition drive passed the restaurant. This was the type of vehicle Poppy said she drove. Frank watched this vehicle park. A woman in her late thirties stepped out of this top of the line vehicle. She was: five foot six, had long straight blond hair, smaller breasts, wider hips, a noticeable backside, and attention getting legs. She wore: brand new European style round glasses, a short length European styled black casual denim dress, it hugged her body without being inappropriate, this dress was layered over a long sleeved white t-shirt, she was wearing a pair of black leather sandals, and her black and white purse hung over her shoulder.

She: locked the doors, placed her keys into her purse, and looked for Frank. She spotted his red shirt. She waved to him. He: stood up, waved in return, and pointed toward the entrance. Seeing this she set her cell phone into her purse. She noticed he went into the restaurant and was meeting her at the door. She appreciated this. As a lady she headed toward the entrance of the restaurant.

* * *

Poppy came from a wealthy family. Through the many generations the family had it's ups and downs; but they never lost it all nor where they the wealthiest. They gained their wealth when Poppy's distant grandfather observed the first mill being constructed. He convinced a few finical backers he could build one as well; these investors took the chance on him. He started a mill in northern England. In a short time all of the investors and the grandfather benefited from this grandfathers vision. This mill became one of the first companies in England. A community grew around this mill. Since the beginning of the industrial revolution her family was involved in community matters. Because of this, her divorce became the talk of the community, and for a few days a national story.

With all of this publicity and her undeserving poor reputation she decided it would be wise to live in America for a few years. In the community she grew up in she was considered a "slapper." This was very hurtful. She received this reputation when a friend of her Brother secretly watched her masturbate then claimed he had sex with her. The reason this was a hurtful reputation was due to the fact she only had sex with two people in her life; and one of those she never went all the way with. The guy she never went all the way with was a steady boyfriend she dated before meeting her Ex-Husband. The reason the divorce became nasty was because her Ex-Husband tried to use her reputation as a "slapper" against her. This was deeply hurtful because he was the one who cheated on her with multiple mistresses. It was proved he was the one being disloyal but the false reputation stuck to her like glue. She felt fortunate to be working for an international food company where moving to the United States was easy. She believed it was her destiny to move to Minnesota. Her Aunt and Uncle already lived there and a large lab for the company was near by. The Aunt and Uncle met while he was on leave during his service with the US Navy. As soon as his service was over they married. When he was finished serving in the US Navy, the Aunt followed him back to Minnesota; where they started a family of their own. Poppy appreciated how helpful this extended family was to her.

Poppy often fantasied about her first love. The most powerful orgasm she ever experienced was from this lovers touch and tongue. She believed he never asked to go further because of his micro penis. At the time, she wasn't ready to go all the way, and she wanted her first time to be with a bigger guy. She incorrectly assumed any guy who loved her would be an attentive lover. When she enjoyed herself she often imagined receiving oral sex and a guy paying attention to her small breasts. When she imagined intercourse she imagined a guy easily slipping it in without it hurting. The evidence of this was the small sized toys she often used during masturbation. She no longer wanted to experience pain during intercourse.

A month before meeting Frank, Poppy posted an ad seeking an ongoing friend with benefits. In the ad she: mentioned interests outside of the bedroom, was uninterested in a long term relationship, focused on the fact the friends part was important to her, she was straight, wanted to be with a guy who was single, wanted only one understanding friend, wanted a giving partner who enjoyed foreplay, mentioned her desire of receiving oral sex, she admitted she was leery of performing oral sex, and mentioned how she preferred to be with a guy who was average sized or smaller.

The amount of responses she received were overwhelming. The first annoyance was the one or two word responses. She disliked the rude responses. She wondered how many dates a guy received by just sending a dick picture; this was either small or big. At some point she wanted to see what a potential friends dick looked like but she wanted to receive this picture after a few emails or a conversation on the phone. She was annoyed at how many married men answered her ad. She knew what it was like to be cheated on; she would never be the other woman. She was surprised on how many women and couples responded to her ad. Anytime a couple responded she immediately thought of her Ex-Husband pressuring her to have a threesome with another woman. She felt she made it clear she was a straight female looking for a male friend. The idea of kissing another woman or performing oral sex on a woman was a huge turn off for her; she was certain she would feel uncomfortable if a woman tried to give her oral. The least thing she wanted was to share her bedroom with another. She knew of people who were into threesomes and group sex but this was something she would never participate in.

Whenever a guy: bragged about his large cock, implied she would be happier with a bigger guy, sent a picture of his big cock, sent a rude response while referring to his large cock, or did all of the above; this reminded her of how painful sex could be. Her Ex-Husband was a lazy inattentive lover. He believed all he needed was his big dick to please a woman. Only after she cried and pleaded to be taken to the doctor did he start to engage in foreplay. He made her feel like foreplay was a chore. He was in a rush and consistently asked if she was ready. Receiving these big dick pictures reminded her of the times she gave him oral sex. He often pressured her to have oral sex; this killed any desire to participate in the act. Plus, when she gave him oral he was often times aggressive during the act. This was horrible for her because it took some mental preparedness to engage in this act. What made the experience even more terrible were the times he would criticize her for gagging. He complained anytime she wouldn't swallow. Even more hurtful was the fact he cheated on her. He justified his behavior by accusing her of being a terrible lover and by reminding her she was known to be a "slapper."

One of his mistresses broke down in from of Poppy and apologized for having sex with her husband. The mistress claimed at the beginning of their affair she never knew he was married; Poppy easily believed this. After the mistress found out he was married she confronted him, he promised he would divorce Poppy; of course he never did. The affair was the final straw for Poppy. After the divorce, a few more of his mistresses approached Poppy and apologized. After becoming friends with the first mistress, this mistress confided to Poppy something Poppy knew; just because a guy had a large cock didn't make them good lovers.

This was the reason she mentioned in her ad she wanted a guy who was average to smaller. Having smaller guys send her responses had different issues; it was obvious many of these guys lacked confidence, a couple of them didn't even show up to a planned date, many were afraid to send her pictures of their cocks, many were desperate, and a few were needy. The three guys she actually met were uninterested in the friends part and were only focused on sex. She truly wanted a friend and wanted to make sure this would be on going.

Before deleting her ad she decided to check out the Men seeking Women ads. Many of these ads were exactly like the responses she received; even still she responded to three ads. She felt, out of the three guys she contacted, Frank was the most sincere. Out of all the pictures she received, both in response to her ad and her correspondence over email, she felt Franks were the best. She liked the fact he waited until they talked to one another over the phone before sending any nude pictures. Being in his early fifties he was far from the best looking guy but she felt he had the best presentation. She felt it was bold of him to place a six inch ruler next to his cock, take the picture, and send it to her. She believed with his cock being four and half inches when erect this showed how confident he was. He sent her two photos of him dressed; one was in a casual outfit and the other was in a suit. He sent him three full nude photos. He was standing in front of a bathroom mirror; one was a side profile with an erection, one was a frontal with him having an erection, and the other was a frontal with him being limp. In addition he sent her three drawings of cartoon animals in specific sexual positions. These positions highlighted the best positions for the woman when a guy had a smaller penis. She felt these photo's were tasteful and it proved he was thinking about her.

After: numerous emails, a conversation she had with him over the phone, and the pictures he sent. She started to send photo's of herself. In the one of the pictures she was wearing a flowered skirt and a simple striped shirt; teasing she was without a bra. In the second picture she was wearing a dark blue dress without a bra; she made sure the outline of her breasts and her nipples were clearly visible through the fabric. After expressing how much he liked her small breasts and how he liked it when women wore denim. She sent him a series of photos of her wearing the tightest pair of jeans she owned; she was topless in two of these photos. After she sent him the tight jean photo's he wanted to see her backside without clothes on. She was surprised he would want to see this; she felt her backside was her worst feature. It made her nervous but she send him two pictures of herself completely nude. The first was a simple full frontal picture. In the second she was turned around showing him her backside. If she mistrusted him in any way she would have never sent these type of photos. She knew how embarrassing this would be to herself and her family if the media got a hold of these pictures.

* * *

There was an awkward silence when they first sat down. Both were grateful when the waitress came by and took Poppy's drink order; she ordered a red wine. He causally started the conversation by telling her what were good menu choices. This led to a fun conversation about the differences between American and English dinning.

Frank felt Poppy was more attractive in person than in her photos. He: adored her long oblong shaped face, felt her pronounced cleft chin gave her face character, her long pointy nose seemed to fit her face, her round cheeks added to her beauty, he adored her light green eyes, her perfectly trimmed blond eyelashes made her eyes stand out, and he adored her European style glasses. He absolutely liked her long beautiful blond hair; he felt the part in the middle was perfect. He loved it when she smiled or laughed. What he found delightful was her strong English accent and the way she would wave her hands when she talked. He found himself imagining what her small perky breasts looked liked under her denim dress and white top. What he liked the most; was how smart she was, how feminine she was, and how fun she seemed to be. He wondered what fool would cheat on her.

Poppy loved their conversation. Before, during, and even a little after the meal they discussed: her interests, chess, playing football when she was in University, they briefly discussed American football, they discussed the difference between the American version of Monopoly and the English version of Monopoly, WW2, she found it sweet on how he talked about his deceased wife, she could tell he loved his three daughters, she found herself telling Frank on how she discovered her Ex cheating on her, vaguely discussed her upbringing in England, and they talked about their jobs. This was a completely different experience than the other two guys she met. All they wanted to talk about was sex and rush to a hotel room. She felt, she could have strung this out, to three or four get "dates" before he would assume they were having sex. Just as she started to question if he was interested in her sexually; he mentioned an email she sent.

After he sent her the picture of his cock next to the six inch ruler, she sent a one sentence reply, "You have the type of cock I'm looking for," and the series of jean photo's. On the phone, with her nudging him, he admitted to masturbating to these photos. He shocked her by telling her how much he loved her perky breasts and wanted to see her backside without the jeans.

Poppy found their current sexual conversation to be refreshing. She admired his maturity. She thought of the claims of her friends both in England in the States that older men were better.

She became wet during this conversation. She never became aroused by anything directly he said it was his: interest in what she felt, his interest in her desires, and what her boundaries were. Never once did he seem rude or crass. Never once did she ever feel like he was demanding sex. The way they ended up discussing their: expectations, their desires, and their boundaries made her want to have sex with him. She felt it was refreshing to talk to a man who brought up boundaries and didn't find it offensive she disliked oral sex. She found it funny when he asked her if she was against giving a good hand jobs. She answered, "Want to find out?"

She found it sweet when he asked, "Now?"

She smiled, winked, touched him on the arm, "I'd like to start the benefit part of our friendship."

Frank was surprised she wanted to start at this moment. He expected them to have a few more conversations over the phone and a couple more "dates." But, being the man he was; he had a plan just in case she was ready.

* * *

After passionately kissing and casually touching one another Frank slid off her denim skirt. He teased her nipples by kissing them through her white t-shirt and her bra. He loved it when they became erect. When he noticed her provocative purple panties he wondered if she was wearing a matching bra. Remaining patient, he began to remove her t-shirt; she helped him remove it. He stepped back to to admire her matching bra and pantie set. He became erect. Lingerie was a thing for him. A thing his wife bulked at. He always wondered why his wife was uncomfortable wearing provocative lingerie. Seeing Pappy wear this provocative bra and pantie set was a real turn on. He started to mouth her nipples through the bra.

She kept waiting for Frank to rush it; but he didn't. She needed to tell herself to relax and enjoy. She reminded herself he said this first round was for her. The idea of a "first round" bounced around in her mind. She was used to only having one round. To have multiple rounds was intriguing enough but to have a round dedicated to her; was mind blowing.