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- I Did It For The Money -
Straight Male / 27

I Do Old Women For The Money

For about 2 years now I have sex with old ladies for money. I moved to Florida for a new job and it was going well. I made decent money, but not so much that I could afford that new Corvette I wanted. Well one night after work I was having drinks with colleagues and a senior partner was talking to me asking me a lot of personal questions, was I involved with anyone, was I straight, and so on. We had already had enough to drink to not be able to legally drive when she said what would change my life forever. Would you fuck an old broad like me for money? It totally took me by surprise but I just blurted out hell yeah. What I didn't realize was how much she was willing to pay. We got a Uber and went to her place. A mansion by my standards, very nice indeed. We went straight to her bedroom and she started unbuttoning my shirt and I did hers and we ended up naked in minutes. She's not a bad looking woman even at her age, near 60. Tall thin, small tits, shaved pussy. I hadn't had sex in a while and was very horny. But I took my time and seduced her. Kissing her passionately then the back of her neck then her nipples which responded nicely, I kissed my way down to her pussy and ate her to quite a few orgasms. She has a nice pussy. It tasted and smelled great. I'd never had sex with anyone near her age so I didn't really know what to expect. I then fucked her brains out for at least 45 minutes before busting a huge load in her old pussy. We laid in her bed after for a bit kissing laughing and talking. I went back down and ate her old snatch again licking my cum out of her then fucked her again, and after a few minutes she said fuck my ass stud. She had lube in her nightstand grabbed it, and slathered it on her ass and my raging hardon. I plowed her ass like my life depended on it and she fucking went wild. Fuck my ass you young buck. Yes fuck this old bitch! I did as I was told and eventually unloaded in her ass. We fell asleep after and woke later in the morning. We showered and I ate her out again then fucked her one more time. She gave me $1500 bucks for the best fuck she had in years. We had breakfast and she told me that she had lots of friends who would pay me even more for the same treatment. Fast forward to today... I've been fucking her and 12 of her friends regularly. I paid cash for that Vette a year ago. And have over $50K in the bank. Yeah most of them aren't nearly as hot as Miss K. But they pay well. There is one who is really fat and gross to be honest. But she pays me just to suck my dick and then once in a while I'll put it in her pussy and fuck her for 10 minutes and she's extatic. She pays me $1000 if she just blows me and double if I fuck her. It's gross for sure but for just a few minutes a couple times a month I make good money. I still work but it's remote and I've actually fucked many of them while on the clock.

I do fuck Miss K a lot. And for free now. I love fucking her actually, she's the best piece of ass I ever had. I absolutely love fucking that ass and she goes crazy when I do. I also love eating her pussy and do it every time we get together. She did buy me a condo on the beach. But she has a key and the only stipulation is that it is our place. No one else gets fucked there. I'm good with that. She really treats me great. And my real confession is that I love her. We do spend a lot of time together. We go to expensive restaurants all the time and go on cruises and such. We hold hands and kiss in public as if we were just another couple.

I'll probably fuck these old ladies until they want me to stop. But I'm investing all this money and getting my broker's license soon and won't have to work after age 30 and I'll be very well off. How lucky can one guy get? If Miss K asked me to stop fucking all of her friends I would though. I don't think it'll happen because she loves hearing about their experiences with me from them. And I do her for free! She calls me her boy toy but one time when she had a few drinks too many she said she couldn't think of her life without me in it. I feel the same Miss K. I love you.

3
# 62356 - by Deuce / December 2, 2022
- Embarrassing Moments -
Straight Female / 32

Stepson Is A Handful.

Earlier I responded to a post about stepdaughter confessions. After saying I didn't have a stepdaughter but I had two teenage stepsons, I thought perhaps this would be something worth sharing.

Two years ago I moved to Florida looking for a fresh start after a divorce. I met a great guy, a captain in the fire service. He's a great guy, a little older than me (he's 39). About a year after dating, he proposed and we got married. He has two teenage boys (14 and 17) from a previous marriage. When we were discussing marriage, he cautioned me that his boys could sometimes be a handful. I was so happy to have such a great guy and a new family and I told him I knew " boys will be boys" since I grew up with two brothers .

So my husband works a lot of 24 hour shifts and I'm home alone with the boys. The older boy has a GF and spends a lot of evenings going out. The 14 year old, Brett doesn't get to go out a lot on school nights. Sometimes after dinner I love a few drinks and a swim in the pool and Brett often joins me

Like normal, I'm floating around on a my inflatable raft and Brett comes up behind me and flips me over in waist deep water. We go to wrestling and laughing ,when I find out my top is pulled down and one boob is showing. I turn my back , then the little shit manages to unsnap my top. We wrestle some more and Brett throws my top on the side of the deck. I'm yelling and laughing at the same time. He tries to climb on my raft and just for fun, I grab him from behind and yank his underwear down and throw them up by the pool stairs.

I dumped him off the raft and told him to go get my top. He laughs and says" Ok" and he walks over to the steps. When he climbs out naked walking around, I can see him in the pool lights. He has a beautiful cock, maybe 6 inches or so just swinging around as he looks at me grinning.

He tells me if I want my top ,I have to come and get it. I walk over to the steps with my 34Cs exposed and as I'm putting on my top, I can't help but gaze at his now hard young cock. My husband was right, this one was definitely a "handful".

4
# 62304 - by Annie / November 30, 2022
- I Did It For The Money -
Straight Female / 31

The Promotion 3

Hello again. I cannot answer any other comments, so I will do that here.

I had planned to ask for a test drive but he beat me to the lunch date. I knew what lunch meant and I went anyways.

He is bigger and better than my husband. I love my husband, but this is not his stronger point.

He has asked me to meet him when everyone goes home tonight. And yes, I am sure it is to suck or fuck him.

Yes, I am sure he will want to parade me around when he goes on business trips, but that can be decided when it comes up.

In my mind, and now with my husband on board, I am completely at ease over this. If it gets to be too much in a week, I will renegotiate my Customer Service Manager salary. I have enough in my texts to bury him and he has the same on me, so I do not think this will be an issue.

And by the way, his cock feels really good inside of me. Can’t a woman enjoy being dicked down? Can’t a woman let someone use their body for pleasure? I am on board with all of this, so why can’t I just find my own pleasure as well?

5
# 62308 - by Angela / November 30, 2022
- Men Only -
Straight Male / 58

Sort Of, Kind Of, Got Me A Mail Order Bride

15 years ago I was one of three investors in a high pressure vessel factory in the Czech Republic. One of the Directors was a female Czech PhD. 40ish, must have been a knockout in her early years. She went with me to Kiev in Ukraine to a conference. We had too much to drink, we picked up a young Ukrainian girl in her twenties and we got into bed. She was starving for a girl and I mostly left her alone as she went for broke with the girl. When I got overheated and my cock hurt to fuck, I went for her and not the young maiden. I fucked her, fucked her till I came.

She lost her composure, angry beyond control, she was a partner in sex with the girl, not the object of sex, we were there to fuck the girl. I got a way too long yelling at, she claimed she was a lesbian, she didn't fuck men. The rest of our trip together was awkward, silent. She flew back to Prague, I flew onto Minnesota, via Frankfurt and New York.

She was nervous when she called me a couple of months later. She claimed to be pregnant and wanted to know what I wanted her to do. She could terminate the pregnancy, she could carry it as a surrogate, it was for me to choose. I learned that Eastern European and Russian surrogates was a cottage industry at the time.

For a man my age a child without a mother was a big big problem, so I told her to have it but she was going to raise it. This went over like a fly in her soup. I didn't back down, not even a little bit. When she was around five months on I invited her to visit me. We talked, business to business, we had a joint investment. Sunk costs not withstanding, the future operational costs were the discussion. I told her point blank, no discussion allowed. If I was paying she was coming along with the baby. Whatever solution we discussed she was the mother, she was going to raise the baby.

And that's why this lesbian Czech mother became my wife in St. Paul. Not technically a mail order bride, but at the time thousands of brides came over from Russia and the Eastern Block countries. In conversations with friends and neighbors that was her story, that I found her profile looking for an English speaking college educated wife. She used a baby to hook me, and here she is. She was 38 when she got pregnant and went on for number two. Two older parents who never dreamt they'd have children. She's turned out to be a damn good wife. I'm pretty sure she never was a lesbian.

0
# 62310 - by Fred / November 30, 2022
- When I Was A Kid -
Straight Female / 30

The Almost Threesome

When I was 15, I dated Bobby, a 17-year-old guy I loved, but who kept bringing up having a threesome with another girl. I jealously asked which girl, thinking he had someone in mind. He said just some hot girl we might meet someday, no one in particular. I told him I was wasn’t interested in that, but a threesome with another hot guy might be okay. I was teasing when I said that, knowing he wouldn’t go for it.

We went to a wedding - somebody he worked with at the sporting goods store. He bought a suit for the occasion and I wore a flirty little wrap dress that showed off my slender legs and big boobs so we looked pretty grown up. At the reception, we’d hoped we could drink, but the bartender carded everyone who looked young, and we ended up drinking Cokes. We got bored, and decided to try our luck at the bar next door.

The bar was crowded and noisy. Nobody carded us, maybe because we were dressed up and looked older. I got a rum and Coke and he got a beer, and we found a place to sit in the back. Some guys were playing pool nearby, and one of them kept checking me out. “Still want to have a threesome?” I teased, pointing out the guy at the pool table who was still looking at me.

“You’re funny. Let’s play pool when they’re done.”

We ended up playing pool against two of them, including the guy who’d been checking me out. Jack turned out to be 26, tall, handsome, scruffy, big-muscled. He bought us a round of drinks and then a round of shots. My little dress had a tricky, low V-neckline that kept gaping wide open, flashing my boobs and the lace demi bra they were spilling out of. Jack and his friend didn’t seem to mind, watching me closely each time I leaned over the table with my cue to line up my next shot.

We lost the game, maybe because I’d gotten kind of drunk. My boyfriend had stopped drinking since he had to drive us home, but Jack bought me another one—and I started getting flirty with our new friend. The three of us sat in a booth, with me next to Jack, leaning into him, quietly mouthing “threesome” across the booth at my boyfriend, who shook his head, looking irritated. “What are you kids talking about,” Jack said, stroking my long blond hair and dr****g an arm around my shoulders.

“She wants to have a threesome,” Bobby said, embarrassing me.

“That so?” Jack asked, grinning at me, his right arm resting on my right shoulder, his dangling fingertips caressing the bare white slope of my right boob.

“It was a joke. Just a joke.” I felt like dying.

“You’re cute when you blush,” he said. “There’s a motel across the street.”

I freaked out a little. I was pretty sure it wasn’t going to happen - Bobby wouldn’t go for it. But then Jack left, returning a few minutes later with a motel key card he set on the table in front of me.

Next thing I knew, we were outside in the cool night air, crossing the street to the motel. Jack had his arm around me because it was cold and I was a little unsteady in my high heels thanks to all the alcohol. The room had a king-size bed that could fit three easily.

Jack undressed me while I stood there looking at Bobby like “Is this really happening?” My boyfriend just looked back at me coldly. Once I was naked, Jack lifted me up and carried me to the bed, dropping me on the mattress before undressing himself, looking at me all the while.

“Come on, join the fun!” I said to Bobby, patting the bed. He started taking his clothes off, still not looking happy.

Pretty soon we were all in bed together. Jack started kissing me and squeezing my boobs, and I loved it, but knew my boyfriend was feeling left out, so I turned toward him and kissed him for a while as Jack spooned me from behind, his hands roaming my naked body. Jack was more aggressive than Bobby and turned me onto my back and began servicing my clit with his tongue. I came right away, crying out and looking over at my boyfriend, who stared at me, not happy for my orgasm. I reached out and held his hand, hoping he wouldn’t be jealous. Then I reached for his cock and stroked it but he wouldn’t get hard.

I felt I owed Jack oral, so got on my knees and took him into my mouth. He was bigger than Bobby, and I wondered if that was part of the problem. I sucked on it, which made him bigger still, and I wondered how fast I could make him come. But he didn’t come, and instead pushed me onto my back again, and lowered himself onto me, pushing his cock into me.

He fucked me deep and hard, the bed creaking loudly, the headboard hitting the wall in a steady rhythm, alerting the neighbors to our heated lovemaking. Bobby got up, leaving the bed for Jack and me to use, and sat in a chair. I saw him stroking himself, trying to get hard, while Jack drove me to another orgasm. After that, it was like my boyfriend wasn’t even there - Jack and I were the only two people in the world, kissing and fucking and holding each other close. I came again, and then he came and gave me the biggest cream pie I’d ever gotten. If Bobby had brought condoms in his wallet, he wasn’t sharing.

Jack kissed me and got up from the bed. I looked over at my boyfriend and said, “Your turn.” But he didn’t move - just sat there sulking, his cock soft and sad.

Jack brought me a glass of water which we shared, then he rejoined me on the bed and sucked on my boobs. “Ready for another go?” We fucked again, with me riding him this time.

Bobby’s phone rang, and he answered just as I started coming, moaning on the bed. “Mom. Yeah—I’ll be home soon.” He set his phone down, and seemed depressed when I cried out as Jack shot another load into me.

“We should go,” Bobby said when we were done.

“What about our threesome?”

He didn’t answer.

We got dressed, and I gave Jack a long kiss goodbye and thanked him for the lovely time, and for all the drinks and getting the room for us. He said, “Hit me up if you all wanna try another threesome,” and smirked at Bobby.

On the car ride home, Bobby broke up with me and called me a slut and said all kinds of mean things. I refused to cry until I got home. My parents were already in bed, thank God, so I could just go into my bedroom and let it all out. But the next day, I realized Bobby was an asshole, and I was glad I’d met Jack, who was more of a man than Bobby would ever be.

For the record, I’ve never had a threesome in all the years since, though the idea still intrigues me.

3
# 62313 - by Hailey / November 30, 2022
- I Did It For The Money -
Straight Female / 31

Promotion 2

This is how today went: he offered to take me to lunch and I accepted. I knew what this meant and I did it anyway. I just got back to my desk and I accepted the promotion. I will explain it to my husband tonight and hope he does not go nuclear.

We did not eat lunch. We went directly to a motel and he fucked me - just like the whore he made me today. He fucked me for about an hour, came in my mouth and congratulated me on my promotion. My new title in the company will be Customer Service Manager. To my boss, I am Head Customer Service Manager. Such an asshole, although he retroactively made my new pay into the current payroll, which made today seem okay.

Now for my husband…ugh. Wish me luck or tell me I am a bad person, as I probably deserve that too. I am doing it for the money.

9
# 62282 - by Angela / November 29, 2022
- I Did It For The Money -
Straight Female / 31

Promotion

My husband lost his job about a month ago. I am not going to make this out to be life altering and dramatic, as his job was a part time job at Kohl’s…working nights in the stockroom. It worked for our family situation.

Last Wednesday, as we were shutting down for the long holiday weekend, my boss approached me. Word got back to him that my husband lost his job and he offered me an option. He would allow me to call my new option a promotion and yes it came with more money, but I had to assist with his sexual needs too.

I am torn. I mean, it is $300.00 more per week - where I live, that actually means something. I am happily married. I seem to have a good enough life. My husband would not need to work nights. Not that it should enter into this, but my husband and I never have sex anymore as we are on totally different schedules. He is a practical and easy going husband, so if I told him, I am sure he will not go nuclear. I know what would be required of me by my boss and it isn’t bad from a perspective of sexual situations.

Confused for sure…

11
# 62268 - by Angela / November 29, 2022
- True Sex Confessions -
Lesbian Female / 44

A Story Of A Long Time Ago About Sex At The Office

OK, so this is about work sexual behavior. I went to work for a mid sized local company. The executive secretary was a woman in her early thirties, very attractive and kept herself looking nice all the time. I was in the coffee bar and she walked in and she complimented me on my style. We talked for a minute and she reached and grabbed my boob. "Are these real?" and with that she told me that she really didn't like fake boobs, especially when you touch them. For her it was all natural or nothing.

She was all lesbian and she set her eyes on me and before I knew it I was laying on my back with her face between my legs. For me it was a new surprise. A surprise in that I liked it and I was doing it. She was right, natural boobs are best when it comes to playing with them and kissing them. She is all natural too.

One day, many months later, after playtime in bed, I asked her how she got her job. Well, she worked in another department and when she started having sex with the owner he moved her into her current job as executive secretary. I was shocked, a little, but not surprised. I told her I thought she didn't go that way. She said she didn't, but that's how it turned out and he paid her better than she was making and after a couple of years you sort of get used to it.

The next morning, a lazy Sunday morning, we were laying around just looking at each other, she told me that her boss, the owner, had put his eye on me and he had asked her if she thought I might make into his bed. She had put the conversation off, but since we had talked about her and him she was asking. It would be good for my career and she would be there so I didn't have to face it alone. She went on to tell me if giving him head turned me off, she would suck him and then he could get on with his business with me.

The getting there took some time, but we went to his beach house one Saturday and she showed me off to him, she gave him a blowjob and while he was erect she had me lay back and he did what he wanted to do. It had been a long, long time since I had sex like that, since my mid teen years in high school. It was way different, but I was fine with it. He let us pet and make out after.

For the next long while, we had these three way sessions. He took turns, not the same day, but turns with us and I learned over time to give him blowjobs (which was like facing my worst fears). The sessions became routine, we did it from time to time, it wasn't a regular thing at all.

But that was then, and this is now. I live with her in Tampa where we moved during the pandemic to be close to her family and he got COVID real bad and had to close his business down. Being twenty something is one thing but now I am in my forties, and he is in his seventies so it's just memories. Although I am still fond of him in a paternal sort of way. When I first got together with her I never thought that it would last 20 years.

0
# 62273 - by Carla / November 29, 2022
- Anything Goes -
Straight Female / 25

Parents Neighbor Stuffing My Turkey

Was back home at my parents for thanksgiving. They live in a small village in Ohio. I moved out of Ohio right after high school. Won’t say what my job is but I get barely any sex because I’m so busy.

My parents neighbor is a really nice guy. He’s been living there for years. His wife died when I was a teenager. Both his sons are older and live elsewhere

Thanksgiving morning I was outside going for a run. And when I showed up back at home my parents neighbor was outside in his robe taking his dog out. So I decided to stop and chat. I’m wearing yoga pants a sports bra and a zip up jacket.

Then he says I got coffee on want some? So we head inside his house. He comes to my parents thanksgiving every year so we were just hanging out and talking. As we are sitting in his kitchen I noticed that he had no pants or shorts on under his robe. His dog was leaning on his leg which pulled his robe open exposing his underwear

Plain white briefs. No shocker to me as he’s older. He noticed they were visible after awhile and said oops let me fix my robe. But me being a big flirt I jokingly said it’s fine I’ve never seen a guy in briefs before.

There I am flirting with a guy who is 69 but looks way younger for his age. To be honest after I go running I’m SO horny for what ever reason I don’t know. And at the moment I couldn’t help but think about taking his dick. So I gradually flirted more till he caught on.

Eventually I was in front of him opening his robe and pulling his briefs down. This man had a pretty decent size dick in his briefs. Shaved and uncut. I was very surprised he was shaved. A nice bald cock to suck on.

At first it was just a bj but I wanted dick so bad. I told him I’d get naked too but I’m probably stinky from running. His reply was a natural scent isn’t going to stop me. So off to his bedroom we went after I stripped naked in his kitchen. Thank god I shaved the night before!

He wasted no time eating and fucking my pussy. He was my first uncut dick too. It felt amazing. I orgasmed a few times then he started to moan loudly! He came in me pussy. Totally thought he’d pull out but I can’t deny that I love a good creampie.

Once he pulled out I made sure to lick any remaining cum from under he foreskin. His cum was so sweet tasting! Best I’ve had. Then we laid there naked for a bit before I got dressed to head back home to shower and get dressed since family was showing up. He needed to shower too.

Throughout the evening cum was leaking into my thong. I was totally unaware how big of a load he shot in me! I had to change my panties and put a pad in mid thanksgiving. And me being naughty I decided to slip my thong in his pants pocket when I saw him alone in the hallway leading to the bathroom. He definitely was surprised!

The following day I had sex with him again. He admitted I was the first pussy he’s been in since his wife passed and he honestly forgot how good it feels.

We had sex one more time before I left but assured him when I’m visiting home I’m coming for dick too.

4
# 62278 - by Hailey / November 29, 2022
- I Did It For The Money -
Lesbian Female / 33

Mature Lesbian Housewives And Mothers

For the first 25 years I was an active lesbian, never an activist but voting for the usual slate. I met my now best friend at work, we are both nurses, who is also lifetime lesbian. We dated but we became closer as friends. In one of our many late night conversations the topic of lifestyle, children, husbands came up over and over.

We agreed that getting married and settling down with a couple of kids and a big house was what we wanted. We changed our life, and after cleaning up our social profiles and changing jobs to hospi4ale where we weren't known, we went husband shopping. She married a lawyer, and I married a doctor, divorced with children.

We live our parent's lifestyle, we have our kids and have adopted the wife roles to our overly busy husbands. We are best friends, our husbands get along enough. We have our lesbian moments, but we keep it between us. We've questioned our true lesbian credits, and we are who we are. We don't see ourselves as being in the closet, we are more of lesbians adapting to our realities. Is it the money, the security. Yes. Since we got married we have met other housewife lesbians, like us they made the same decisions. We can't beat them, so we joined them.

1
# 62231 - by Lady Gaga / November 27, 2022
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