My Affair with Roxy

If you're thinking about having an affair, don't do it. If you're looking for sex with someone other than your wife, find a call girl and pay her. I know this is something that the male ego can't deal with but trust me, in the long run it'll be cheaper, with less drama, less stress, and less heartbreak.

When I was working, I traveled extensively and sometimes would go out alone at night to a singles bar looking for the hottest BBW in the crowd. Most times we'd just chat and have a few drinks at the bar, a few times we'd go back to my hotel room where we'd go no further than some pussy licking and a blow job, but one time I took it to the next level and that's how I started my affair with Roxy.

I was in Orlando for a weekend conference and, after three days and two nights of seeing the same people, I had to get out of there. I snuck out and asked the valet for a fun club with lots of women, he hailed a cab for me said take him to The Kook.

I got there about 9pm. It was getting crowded, but I saw Roxy right away. She was the answer to my fetish prayers, a tall BBW in a white pants suit with short platinum blonde hair and huge tits.

Roxy was with two of her friends at a high top just off the dance floor. I went to the bar, ordered a drink, and told the bartender to send a bottle of champagne to her table. I watched the entire process develop the way a director sets up a scene, the bartender put the champagne in an iced bucket with three glasses, the waitress picked it up, brought it to the table and popped the cork, the girls started giggling and clapping, the waitress pointed at me, Roxy motioned me to join them, and the rest is history.

We went back to Roxy's house where we engaged in so much more than pussy licking and blowjobs. We fucked and sucked and licked all night. She came non stop and just when I thought she was finished she'd sucked my cock to get me hard again. Towards the end she was riding me with her tits hanging in my face. I was so worked up I started sucking her tits and she started screaming for me to mark her. I let loose and started sucking and biting each massive tit. I climaxed first sending a massive load inside her, when she finally came her eyes rolled in the back of her head and she collapsed on top of me.

We laid there for a few minutes and then I nudged her to move her over so we could sleep. She wouldn't move. I finally shook her and she woke up. She asked me what happened and I told her, she looked at me and said that last orgasm caused her to pass out and then she kissed my neck and we both passed out.

I woke up the next morning and tried to assess the damage. Roxy was spooned up behind me and her bedroom smelled like cum and sweat. I looked at my watch it was just shy of 9am and the first thing I thought about were all the missed calls I likely had from my wife. But that was tonight's problem, the current problem was how to get back to my hotel, gather up my gear and get to the airport for my flight back to Atlanta.

With Roxy sound asleep I figured I had a little time to form a plan. That thought was shattered a minute later when I heard a door slam and voices in her house. I woke her up to tell her there are intruders and we have to call the police.

Roxy was having difficulty focusing for the first few minutes. She was hungover and was having a hard time standing from her repeated orgasms. Her tits were starting to show the results of my sucking and her pussy was raw from the last round after her natural lube ran out. But as soon as she heard the voices she got very focused. She told me it's her parents and they must have dropped by early to bring her daughters back and there's no way they can see me. She explained that she's in a massive child support dispute with her ex and getting caught with me in her bedroom will be a problem.

I told her to take a shower and get cleaned up. I gave her $200 and told her to take everyone to out to brunch, once they leave I'll get cleaned up and get a taxi back to my hotel. She took the money, went into the shower, got dressed and headed out with her parents and her daughters.

So now it's my turn to salvage the day. I took a shower, got dressed, called a taxi, and got back to my hotel. Fortunately no one from my company was around so I went to my room, packed my gear, listened to the 10 voicemail messages from my wife, and headed to the airport.

I had a couple of hours before my flight took off and was dying to call Roxy, but I didn't know if her parents came back to her house after brunch so I didn't call. I did call my wife to let her know what time I'd be home and all she said was fine, nothing more, nothing less.

The plane ride was uneventful and the limo ride home even more so. When I walked inside my wife was cooking and watching TV. I walked in, gave her a kiss on the cheek and asked what she's watching. She described it in great detail and asked about the conference. I had already decided to let her bring up the calls and then I'd feign ignorance and tell her I never got the messages. She did, I responded, and then she told me there's something wrong with her phone. She said she left her sister and me a bunch of voicemails and neither of us got the message. Sometimes you need a little luck.

And my luck continued the next day when I got to work and all the buzz was about the fight that broke out between two salesmen. No one missed me, in fact most people thought I was there. So I spent the night fucking Roxy's brains out and no one knew where I was. Can it get any better than this?

I was trying to decide if I should call Roxy when my phone rang with a 401 number. I knew it was her, but I let it ring a few times. When I picked up she sounded different, it was her sober, non-orgasmic voice. She thanked me profusely for the money and for thinking quickly with the brunch plan.

She told me her daughters were going to be visiting their father the weekend after next and was wondering if I could come to Orlando. She said she really felt a connection and wanted to spend more time with me. I swallowed hard and told her I felt the same way, but I'm married, not happily, but married nonetheless.

I thought she was going to unload on me, but instead told me she's not surprised because all the good guys are always married. I told her if she wanted to end it I understand. She asked me if I was happy in my marriage and I said no, she asked me if I was going to leave my wife and I said not likely, she asked if I cared for her and I said yes...she said that's good enough for her. She said life is unpredictable, she understands the situation, and wants to move forward. Unbeknownst to me, this was the best day of our relationship.

That first year we saw each other as often as possible either at her home in Orlando or I'd take her with me on business trips. I took her to Ft. Lauderdale, San Francisco, Palm Springs, Miami, Dallas, Denver, Savannah, New Orleans, and Kiawah Island, just to name a few. But as much fun as we were having, things eventually started to fray.

First, what I discovered was for all Roxy's positive physical attributes and brilliant mind, she had other, darker issues that became apparent the more time we spent together. She had severe mood swings almost every month that were very difficult to deal with.

Second, I always drank a lot, but with Roxy I took it to another level. There's no doubt we were becoming alcoholics which probably exacerbated her mood swings and led to riskier behavior like engaging in sex in public areas and ignoring proper birth control.

One time she accompanied me to Ft. Lauderdale where I had client business. We went out for dinner, got drunk, and Roxy wanted to go dancing so we drove to a club I knew in Boca. Roxy was wearing a leather skirt with a bustier and a blazer and looked incredible. We got a booth off the dance floor and ordered a bottle of champagne. We had a glass, started dancing, and then they played a slow song.

Roxy grabbed me and was grinding her tits into my chest. She told me her pussy was dripping wet and she needed to come. I told her we can leave whenever she wants and head back to our hotel. She told me she didn't want to leave because she's having a great time, but she wants me to finger her when we get back to our table.

The song ended, Roxy kissed me, led me back to our table, and we sat down. I was so drunk and horny I reached under her skirt, moved her panties aside and fingered her dripping wet pussy until she had three earth shattering orgasms. To muffle her screams I french kissed her; to this day I don't know what was worse, that we engaged in this kind of behavior, or that we got away with it.

What we didn't get away with was her getting pregnant. Roxy went off the pill sometime after we started our affair because she said she was gaining too much weight. She had a latex allergy so we only used lambskin condoms, but she hated those as well so we generally used the rhythm method...and then one month she miscalculated.

We had been out to dinner and got back to her house drunk and in heat but without condoms. I told her I'd run out and buy them but that wasn't what she wanted. I told her I'd go down on her to make her come, but she told me she wanted my bareback cock, not my cock in a condom, and not my tongue. She assured me it was safe, that she ovulated several days earlier, so she mounted me and stuck my cock inside her.

She rode me furiously at first, but then the alcohol kicked in. She came a few times and then I unloaded inside her. I pulled my cock out of her and told her to let my cum leak out on my stomach. For some odd reason very little came out. I left the next day and waited for the call to come.

It came two weeks later with Roxy crying hysterically and telling me she missed her period. She was too scared to take a pregnancy test so she waited it out. Ten days later she got her period which was unusually bloody and clotty. Her doctor told her she miscarried and I knew our relationship would never be the same.

What I didn't understand about an affair, and what anyone who is reading this needs to understand, is sex is a very small part of it, even though sex is oftentimes what starts it. And if you're a successful professional who is having an affair with a single mother of two daughters, at some point sex will become subsumed into financial support.

Of course the financial support starts out small, but builds over time. First it's helping out with an unexpected bill, next it's helping out with the mortgage payment, next it's making the mortgage payments, and next is paying half her monthly expenses. And each time you say yes there's a reward, actually there are two rewards.

First, you feel a massive sense of pride, like the hunter/gatherer every male aspires to be by taking care of his woman and second, she fucks your brains out and tells you how special you are, how much she loves you, how no one has ever treated her this way and how she can't live without you. Guess what, how many of our wives have ever said this to us? None, that's how many and it's freaking intoxicating to hear it.

But it's costing you several thousand dollars a month in support payments plus all the money for airfare and hotels for weekend getaways, dinners with her parents, dinners with her friends, flowers and presents for her and her daughters. I had no idea how I got into this situation, but I knew it wasn't what I signed up for. I was paying half of Roxy's monthly living expenses and there was no end in sight. And then it got worse.

I was in my office on a conference call when my mobile went off. It was Roxy and I texted her that I'd call her back. She said she has to talk to me now, but I told her she'd have to wait. By the time I called her back she was incoherent. She had been drinking and told me she had great news, she had a fight with her boss and quit her job so now she could spend more time with the girls and the four of us can live as a family. I told her that wasn't a good idea and that while I was happy to help, I never signed up for a lifetime of supporting her and her daughters.

She went crazy, screaming into the phone that I only wanted to fuck her and that she was going to call my wife. I told her if she wanted to call my wife she could do so, but she would never get another dime from me and I hung up. She called back several times but I didn't answer the phone and she didn't leave a message.

Roxy called back three days later and I let it go to voicemail. When I picked up the message she sounded different, she hadn't had a drink in three days and you could tell. I called her back and she apologized for her behavior on the phone and asked if she could see me. I told her I didn't think it was a good idea, but she insisted so I told her I'll meet her at bar in the Hyatt Regency Hotel at the Orlando Airport in two days.

I got a table in the bar and ordered a Diet Coke. I also quit drinking and it felt great. Roxy walked in looking terrific. Her complexion improved, she lost a little weight, and she was calmer. We gave each other cheek kisses and she ordered a club soda with lime. I tried to complement her on her appearance but she quickly cut me off to tell me it's over.

She told me she thought she could keep doing it but she can't. And while the traveling was great and the alcohol, money, and presents numbed her shame, the reality is we're never going to be together and she was always going to be the other woman. She told me she loves me and knows that I love her, but she has to find a man who loves her and only her.

She told me getting pregnant was the last straw for her because instead of it being a joyous moment of carrying our child, we were both praying for a miscarriage and that is too toxic to live with. She said she's hoping to get her old job back and will know in a couple of days. She asked if I could pay this month's expenses and she'll pay me back when she can. I told her she didn't have to do that but she insisted because she needed to get back her self esteem.

I tried to respond but she put her hand over my mouth. She got up, gave me a hug, told me she will never forget me, waved goodbye, and walked out. I sat there and cried for the next two hours, not because I thought she was wrong, but because I knew she was right.

I reached out to Roxy several years later after she moved to the Florida Panhandle. I was going to be in Pensacola and wanted to see if she'd like to meet for dinner. She told me she was seeing someone and didn't think having dinner with me was a good idea. I agreed and hated myself for even making the call.

I stayed married to my wife and we just celebrated another anniversary. It's a loveless marriage of convenience and at our age we're not going anywhere. But I think about Roxy every day and wonder about what might have been.