Sugar Daddy

It was difficult to sleep that night. I was naturally worried about the girls and what they might be doing. I didn't want them getting too drunk or hurt and I tossed and turned most of the night. Over the next couple of days, I overheard a few conversations between Jenny and Sara that confirmed my suspicions that they both got laid on prom night. It was a humbling moment for a father. You know that your daughter is going to have sex before marriage but you don't want to know about it. I was even more envious thinking of some inexperienced teenage boy having sex with Sara. He probably didn't know how to please a woman like a more mature man could, someone like me. I felt conflicted because I wouldn't cheat on my wife anyway. Sara would only be staying with us for a couple of more months anyway when she'd be off to college in a city about 500 miles away.

Over the next few months, Sara continued to tease me with her young body. I became bolder in my stares confident she was showing off on purpose and seemed to even welcomed my attention. She also became more daring in the more frequent exposure of her shapely figure. One evening when she was wearing a short skirt, she would flash her neatly trimmed pussy by opening her legs when no one else was looking. The little cock tease knew she was driving me wild. As usual, rather than acting on my manly urges, I retreated to my bedroom to jerk off once again.

Unfortunately, Sara's relationship with her mother and step-father only got worse to the point where they weren't even speaking anymore. They didn't even show up to see her graduate. Maryanne and I became her defacto parents for the rest of the summer until we took her to her college dorm and even helped pay for her books and other fees. Sara always treated us with kindness and respect, we were financially secure so we didn't mind helping her out.

Before she left for college, Sara continued to tease me. It got easier seeing it was summertime and we had a pool so I saw her in her bikini and skimpy summer clothing daily. I held firm in my resistance to make a move on her no matter how difficult she made it for me. One morning on her way to her room from the shower, Sara "accidentally" lost her towel right in front of me. I had seen her naked before but seeing her that close gave me a new appreciation for her exquisite youthful body. I couldn't help but stare at her long tan legs and torso, and her pussy. Her tan lines highlighted the white skin of her breasts and ass.

I had mixed feelings as part of me wanted to take her into my arms, carry her into my room and fuck the shit out of her. The other part of me was proud for my family that I somehow found the strength not to act on my natural impulses.

Sara casually bent over to pick up her towel, lifting just enough to only make a half-hearted effort to cover herself. I watched intently as she walked back to her room, her lovely ass wiggling with each step. Once again she looked over her shoulder to see if I was still watching, which, of course, I was. What normal man wouldn't?

After Jenny and Sara left for college, Maryanne and I were now empty nesters. I tried one more time to revive our sex life and my wife gave it an honest effort, however, after a few months, we were back to square one. We loved each other deeply but Maryanne still had no interest in sex. She even repeated her offer to understand if I satisfied my manly needs elsewhere. I, of course, told her there is no way I could ever do that to her.

My sex life returned to scanning the Internet for various porn videos to fuel my masturbation fantasies. My interests drifted towards videos of older men fucking younger women in every way imaginable. It was even better when I found a porn star that reminded me of Sara. I stopped feeling guilty about my inner desires to fuck her seeing she was no longer around the house to tempt me to act upon those feelings. For once, the brain in my head was overpowered by the thoughts instigated by my dick.

Over the next several months, I would travel on business to the town where Sara was attending college and we would have a casual dinner if she or I weren't too busy. I'd even give her a little extra spending money at my wife's insistence. She had become part of our family in the short time she stayed with us and we could afford to help her out a little. I think Maryanne was sending her money too, not that I cared.

During my Internet porn watching, I also joined a couple of dating sites that matched older men with younger women. They called them "dates" but in reality, the men were paying the young women for sex. I honestly had no intention of ever soliciting a date for any of the women but Maryanne told me several times she would understand if I found sexual relief from someone other than her. I really love my wife so my intentions were honorable, at least to start. Mostly, I would look at the pictures of the young women to give me an image to masturbate to. I prefer real women to porn actors too so that was my rationalization for joining a dating site. I set up a profile without a picture because I didn't want anyone else to recognize me. If they did, they would have to explain what they were doing on the site but I still wanted to be ultra discreet. I went to this site more out of curiosity than to find another woman.

There were a few women that contacted me once I joined and even sent me some unsolicited sexy pictures of themselves in various clothed poses but I never followed through with any of the conversations. It gave me more thoughts for my "spank bank" as a friend called it; a picture or thought to be put away for when you jerk off. I wouldn't go on that site very often but the more I did, the more tempted I got to find a young date while I was out of town on business.

One night while I was browsing the profiles of various young women, or sugar babies as they're called when I noticed that one of the girls looked like Sara. I clicked on her profile and, holy shit, it was her, the girl that lived with us for a few months, who mercilessly teased me with flashes of her teenage body. She said she was a student looking for help with living expenses and loved spending time with mature, generous men. To be honest, I had mixed feelings.

Part of me was disappointed she had to resort to "dating" older men because of her shitty home life but the other part of me was thinking, "Now's my chance. Heck, I was giving her money anyway, I might as well enjoy some of what she's giving to other men probably for less than what I was giving her."

I wasn't going to be in her town for a couple of weeks but I decided to message her through the site so there was no evidence on my phone and see where the conversation went. I paid dearly for extra messaging privileges but it was worth the price for my anonymity. She went by the name of Molly online and called myself Alan.

Sara was reluctant to engage in a conversation with someone with so few details in their profile but I assured her that I had to be discreet which piqued her curiosity. I knew her well so she became intrigued when I told her I liked to have long, relaxing conversations in a hot tub while sipping her favorite wine. I told her I liked the music I knew she listened to and was interested in soccer which I knew she played in high school. Despite her reluctance, she agreed to meet me when I was in town which was also aided by my offer to pay her double her normal fee. We agreed to meet at an exclusive Italian restaurant, which I knew was her favorite food. We were to meet at the bar for a drink before dinner.

Sara asked, "How will I know who you are when I get there?"

I replied, "Don't worry, I'll know who you are. Be sure to dress to impress."

For the next week and a half, I was nervous as I had ever been. Maryanne even asked me if everything was alright so I lied and said it was from the stress at work. I found it difficult to be around my wife knowing I planned on cheating on her with a much younger woman who we treated as our second daughter. Every time I saw my wife, I began to have second thoughts about my planned meeting with Sara, however, things changed when I was alone at night masturbating thinking of what I might do with a teenage girl who I lusted after for a long time.

I'm notorious for overthinking situations and I began to panic the closer I got to my business trip. What if Sara didn't want to sleep with me? What if she rejected me and told my daughter or wife? I would then go overboard the other way. What if she wanted a long-term relationship? What if she fell in love with me and wanted more than I was ready to give her? I calmed myself down by telling myself we could simply have a nice, fancy dinner and it was fine if that's all that happened but I couldn't hide my desire that I really wanted to fuck Sara's brains out.

When I got into town, I checked into my hotel and immediately went into a couple of business meetings where I met with some of my larger clients then went back to my room to get ready for my date with Sara. I hadn't been on a date with another woman other than Maryanne for decades and was as nervous as a teenager going on his first date which I found ironic seeing I was going to meet a nineteen-year-old girl for what I hoped would end in one of the most memorable nights of sex in my life. I showered, got rid of my 5 o'clock shadow, put on a freshly pressed pin-striped suit, and went to meet my sugar baby date at an eloquent restaurant that was close to my hotel.

I arrived at the bar early and ordered a scotch on the rocks to help quell my nerves. I tried to rationalize that I was only having dinner with Sara like I had so many other times when I was in town. I knew I was lying to myself because this time was different. Our relationship was potentially going to take a giant leap in another direction. I kept a watchful eye on the entrance anxiously waiting for my dinner date to arrive.

When Sara arrived she looked absolutely stunning in a little black dress that showed plenty of cleavage and her breasts bounced freely, indicating she wasn't wearing a bra. Her five-inch heels made her legs look even longer than they were and were encased in black lace stockings. Her eyes scanned the bar looking for her date and when her eyes met mine she looked horrified at first then gave me a knowing grin. Then smiled widely as she approached me. I gave her my seat at the bar and helped her climb onto the stool with her already short skirt riding up higher on her thighs.

I wanted her to know this wasn't just a chance meeting so I used her fake website name as my eyes scanned her lovely, young body and I asked, "What can I get you to drink, Molly, I mean Sara?"

"I think I'll start with a gin and tonic, Alan, or is it, Roger?

"You can call me Roger."

Sara provided the bartender with a fake ID and we had a casual conversation about school and my wife and daughter but she didn't want to put a damper on the evening and kept that part of the conversation short.

"So Sara, I have to ask, how long have you been going on these dates and why?"

"I've been doing this for a few months now, I like being around mature men rather than college boys. My dates know how to treat a woman. I'm young and want to have some fun so why should I be with some poor college boy when I can be with someone who can give me some of the finer things in life? What about you, Roger? Why are you looking for a date when you are happily married?"

Sara really put me on the spot, but I guess it was a fair question seeing she knew my wife and daughter and I just did the same to her.

"Well, Maryanne and I have a great marriage and we love each other deeply but she's lost all interest in having sex and has even suggested she'd understand if I got some, let's say relief, from someone other than her. I'm not looking for a relationship and I need to be discreet. No one has to know. This really is the first time I've done this."

"Why me, Roger?"

"I think you know why Sara. I think you are an intelligent, wonderful person and you are damn sexy. You were also teasing the heck out of me almost the entire time you were living with us."

Sara coyly responded with an evil grin, "Oh, Roger, whatever do you mean?"

"I never would have approached you, about you know, a date but when I saw your profile, I decided to give it a shot."

"You know I would have dated you if you had just asked."

"I wasn't positive about that but this way there is no doubt about our mutual expectations."

"I understand, Roger."

Now that we had those formalities out of the way, Sara and I went over to the dining area and enjoyed an exquisite dinner at a five-star restaurant complete with an expensive bottle of wine. We caught up on her schooling and what was going on in my life, just like we would have if I had taken her to dinner when she wasn't my formal sugar baby. It was a pleasant evening with Sara looking so stunning. She looked even better than on the night of her prom. Sara appeared somewhat more mature, which took away some of my guilt but still maintained her youthful appearance. I'm sure other diners suspected I might be her sugar daddy but I didn't really care. We would never see them again.

Over dinner, we talked more about when she was living with us and how she liked to tease me. Sara was laughing when she brought up the time she "accidentally" dropped her towel coming out of the shower.

"You should have seen the look on your face when my towel hit the floor. Your mouth was hanging open and your eyes got so wide. I thought you were going to faint."

"I'll never forget that morning, Sara. I thought I was going to faint too. You have an outstanding body and I was pleasantly stunned to see you naked. You have no idea what I wanted to do with you that morning."

Things got serious quickly when Sara stated, "Oh, I think I do Roger. And you know what? I would have fucked you that morning too. I was really horny that day."

"I wanted you too, Sara. I wanted to fuck you so bad. It was just too darn risky to screw around in my own house."

"But risky can be fun, Roger, " Sara replied with a wink.

The tone was being set for what was hopefully going to happen later. I couldn't believe a young woman was confessing to wanting to have sex with me. I knew I wanted her but to have her tell me that was a real boost to my ego and confidence.

When Sara excused herself to use the ladies room, heads turned to watch her every step. Her dress was extremely tight and followed every curve of her ass. Her butt cheeks alternately tightened with each step she took and looked as if they were winking at me as she walked away. Every man in the restaurant was undressing her with their eyes but I was the only one that would be seeing her naked later that night.

After dessert, Sara inquired, "Now what do you want to do?"

"My hotel is only a block away. I have a large suite. We could go there for an after-dinner drink."

"I'd like that Roger. I'd like that a lot."

We both knew what that meant and that's when my nerves kicked in. I hadn't slept with another woman in over thirty years and I was about to cross the line of infidelity. Sure, Maryanne told me it would be okay if I found sexual satisfaction outside of our marriage but I still wasn't sure if she really meant it or was testing me. I went this far to approach Sara and we were now taking a slow walk to my hotel room. There was no way I was going to pass up having sex with a gorgeous nineteen-year-old girl; one who had been teasing me to the point where she became the object of my masturbatory fantasies.

Sara held my arm as we took the short walk to my hotel under the envious stares of men who saw us together and a look of disgust from the women. Yes, I was an older man paying for the company of a woman who was literally old enough to be my daughter but, at that point, I didn't care who saw us together. We were two consenting adults who didn't need the approval of anyone for what we were doing.

When we got to my hotel room, I have to admit, I was even more nervous. I was about to have sex with a hot teenage girl and I began to worry about measuring up to her other lovers. I then remembered she told me how she prefers more mature men because they know how to treat a lady and were more experienced lovers. I figured I would take my time and enjoy her firm, nubile, delectable body.

I knew what kind of wine Sara liked and there was plenty of liquor in the mini-bar for whatever we might want. I poured us a glass of wine and we began a nervous conversation while seated at the breakfast bar of my suite. I felt awkward because I'd never done this before but the more I looked at her flawless, ripe body in her little black dress, I knew I had to have her. Sara's dress was draped over her breasts as her nipples pressed against the satin fabric. Her skirt rode up her thighs allowing the bare skin above her black stockings to become visible. She had her legs crossed and dangled one of her high heels from the tip of her toes.

Sara broke the ice when she told me, "You know Mr. G, I've had a crush on you for a long time."

That statement built up my confidence and I replied, "I was infatuated with your beauty from the first time you came to our house. I felt guilty for wanting to have sex with such a young girl but I couldn't take my eyes off of you. You are a lovely, lovely young lady."

"I could tell you liked me, that's why I teased you as I did. You were so nice to me, I wanted to show you my appreciation. Besides, it was fun to have an older man be attracted to me."

We talked about what was going through our minds when she was teasing me and Sara admitted she would have fucked me but knew it wasn't a good idea with her living there. She told me that having sex with me was so taboo, that it made it even more exciting for her. I didn't know what to say and we stared into each other's eyes for a moment, then, without saying another word, we both leaned in for a long, soft kiss. A charge of energy shot through my body and I felt like a teenager myself and got an immediate erection. I often dreamed of kissing Sara and the real thing was even better than I imagined. It was so exhilarating that one kiss led to another then another.

Sara rose from her chair to stand between my legs so we could continue to kiss. I drew her closer to me as I rose to my feet also. It felt so good to hold her in my arms. My hands began to roam over her barely legal body, firmly grasping her ass as we rubbed up against each other. I'm sure she could feel my erection pressing against her thigh. My hands cupped her breasts which were firm and beautifully formed. Her moans drove my passion to higher heights. I then slid a hand up her dress to massage her through her thong, finding it moist and hot to my touch as I pressed the silky fabric into her pussy.

Things naturally progressed to where I unzipped the back of her dress and she took a step back to shrug it off her shoulder and let it fall to the floor. I began to undress while she kicked off her shoes and slid her thong down her thighs. I had previously seen Sara naked from a distance, briefly when she lost her towel or had seen flashes of various parts but seeing her standing naked directly in front of me as a prelude to having sex, wearing nothing but her black lace stockings will forever be embedded in my memory. I drank in every inch of her ravishing, teenage body. She noticed my appreciated stare and did a pirouette for me so I could take in her alluring body from all sides.

We embraced again in a long kiss then I nibbled on her neck while she stroked my erection. I worked my way down to her breasts, cupping them gently and squeezing her creamy flesh. I longed to suck on her nipples and played with them with my lips and tongue. I then led her over to the bed, laid her down, and began to kiss and suck on her perfectly pedicured toes, kissing my way up to her thighs, then repeating it on her other leg. I was going to take my time and worship every inch of her luscious body. I waited too long for this moment and wasn't going to rush myself.