Q&A: Older Woman Giving Me Money For Sex. What Do I Do?

Q&A: Older Woman Giving Me Money For Sex. What Do I Do?

I started seeing her when I was 18 and I just turned 19. She is 46.  At first, we just had regular sex and would hang out. She would buy me my favorite food and would give me small gifts and I let her know I wasn’t expecting anything in return for spending time with her. She said it was fine and that she wanted to just “spoil me sometimes”.

Then we got a little more kinky.  She started giving me some money, like $50 or sometimes $100 or even more.  I have tried declining, but she always insists on having me accept it. Well she started getting kind of rough with me- like slapping me, scratching me to the point where it leaves marks , biting me, and I even let her spit in my mouth.

I just do it because I like to satisfy her and I want to do things that she likes for her. When she started doing this kind of stuff she started trying to giving me A LOT of money. She tried giving me like $500 and even more, but I feel like that’s too much considering that I didn’t even wanna take the smaller amounts from her, but she insists on me letting her buy me stuff or giving me money. She already bought me a new phone and I don’t want her to feel like I am just using her.

I don’t want to seem ungrateful or like I don’t appreciate her either. What do I do with this money she gives me? Should I return it or what? How do I get her to stop giving me so much?

older women pay for sexVenice’s response to older woman giving money for sex:

It sounds like you have found a sugar momma!  Although I think it’s polite to decline any payment, if she insists, it may be part of her kink.  She may enjoy the idea of fucking a younger guy and paying him for it.  A variation of power or a maturity fantasy.  She gets off on you being a poor college kid that she uses for his penis, helps pay his bills, and has nothing in common with.  She just wants to fuck your brains out.  She probably thinks about this payment during sex, and even during her orgasms.  Knowing she pays you to pleasure her, may be a form of control, but also self degradation.  She may feel that a young man wouldn’t want to fuck her unless she paid his bills, and that gets her off. 

Either way, enjoy the ride and consider yourself lucky.  I’d never pay for a dick.

older women pay for sexRyan’s response to older woman giving money for sex:  

Talk about sex problems that really aren’t problems at all!  Jeez.  This isn’t something most of us deal with.  I’ve never been paid to slang this dick, so I wouldn’t know where to begin.  

Possibly, part of her fantasy is paying a young man to service her.  You have tried to decline, you have done everything you are supposed to do.  If she insists on paying you, take the payment and give her that young cock of yours.  It’s possible she has a form of self degradation.  This can come in all genders and ages.  We ourselves aren’t unfamiliar with doing kinky things that most people find disgusting.  

She may get off thinking a young man wouldn’t want her unless she pays.  Although that isn’t true, it could turn her on to think this way.  This may be part of her kink and how she orgasms, thinking she isn’t good enough for your young dick.  She pays you as a way to build up for her next session with you.  And this works both ways.  It may possibly be a form of degradation, where she wants to treat you like a prostitute.  She may get off using you and then leaving money for you, as if you are just her little boy toy.  Who knows?  But both variations require you to take the money.  What do you do with the money she gives you?  Well young Hugh Hefner,  buy yourself a Versace robe and stop asking so many damn questions!


The Little Things: Bras and Boat Shoes

Boat ShoesWhen someone asks you why you love him, it’s difficult to pinpoint the ways in which he brings joy into your life.  It’s easy enough to say, “Because you love me for who I am” or “Because no one makes me laugh like you do.”  Well, obviously.  For me, it’s not two or three things, but rather many, many small reasons that make our relationship unique and quirky. 

This past Monday, Ryan got off work early and headed to the mall.  He usually heads straight home or to the grocery store on these days.  But when he got to the mall, he called me while I was still at work.

“Hey, V…guess what?”

“What is it?”  I asked.

“I’m at the mall and I found a bra I think you’d like.”

“Really!  How does it look?”

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Sleeping Nude

A few years ago I asked my wife to promise me she will never lay in bed with me wearing clothes. I noticed throughout the years, we began to change our sleep schedules, change where we slept (sometimes I would sleep in different rooms just to be more comfortable), and never woke up in each others’ arms. If my wife was already in bed wearing some shorts and a tank top, I may walk past her and rub her butt, but most of the time I would take my clothes off, hop in bed with my briefs, and go to sleep. Do not get me wrong, we still had a great sex life, but sex and “bedtime” were on totally different schedules. Like I said, we would have sex, then an hour later both be sleeping in king size beds in separate rooms. I like the room completely dark, she likes to sleep with the television on. I like to have a nice side fan blowing on my body, she doesn’t like the cold air.  To most couples this would seem like a huge problem, but we were both complacent.

The truth is, it was a problem. I no longer saw my wife as someone I wanted to hold all night, touch all night, scoot close and curl my stomach around her butt while rubbing my penis against her thighs. I was turning into a colder man who was affectionate during sex, but mentally not there afterwards. A lot of it had to do with my wife shutting down as she appreciated me less. If I wanted to try something new and different, she would agree, but didn’t show any enthusiasm. The sex was never bad, but it lost the feeling of two people in love.

Back to a few years ago. My wife and I both hit a point where we knew we loved each other, but we both had the mutual feeling of boredom. The complacency wasn’t enough. The sex without enthusiasm wasn’t enough. The lack of attention she got from me wasn’t enough.  The lack of openness in the bedroom for me wasn’t enough. We decided, as a couple, to fix it.  Of course, we both had to see the problem to want to fix it.  Our catalyst was the idea that were were no longer lovers or best friends, just roommates.   It needed fixing and we both agreed.

In breaking down a few reasons I had slipped during the years, I knew I never wanted to grow up and sleep with my wife like I was on a camping trip (fully dressed and ready to run in case a bear breaks into the camper). As a kid, I felt that one day I would marry a woman and each night we would lay nude together, her on my chest, talking about our day. I let my wife know that I want her to be nude for me in bed. I want to wake up in the middle of the night and touch her body. I want to know that if I roll over and hug her, we will both be nude. For various reasons, this helped rekindle that spark we had for each other when we first moved in together. I wanted to touch her again, I wanted to hug her all throughout the night, I wanted to rub myself on her and let her feel my naked body against hers. It was sex, without intercourse. A new form of intimacy that even as a new couple we didn’t appreciate. I could hold my nude body against hers for the entire night, falling in love again.

For me, this nudity came very easy. I love being nude, I love showing my wife my body, and I love to feel the freedom of things hanging where they hang. My wife had a harder time with this, as sometimes she would lay in bed with panties and a shirt, sometimes just her panties. I’d come across the bed and feel down her tummy to her thighs and immediately ask why she was wearing panties. She’d look at me, smile, and say she forgot because she wasn’t used to doing it. That’s all it took for her to remove her clothing, but she had to reverse what she had conditioned herself to do for her entire life. For her, sleeping nude didn’t come natural. She felt safe with more clothing. I wanted her to feel safe with me.

After a few months, I noticed my wife would only wear a robe around the house after a shower.  She may put on a sun dress or something simple, but she would not put on a bra or panties. Before bed, she’d slip off her outfit and lay in bed, nude, no covers, letting me see her body. If she is on her stomach reading, I know she wants me to lick and massage her. If she is on her back, I know she is getting tired and wants me to touch and make out with her before bed. She no longer forgets, in fact, it’s just the opposite. At night I will go out with my wife and notice she will not be wearing panties under her dresses. For whatever reason, she has taken a liking to her new freedom, and I enjoy knowing she is breaking out of her shell.  I want her to enjoy her body as much as I do, and how can I not give her attention knowing my wife is a hand slide away from me feeling her vagina or ass? I love it. I love being around her, I love talking to her, I love hearing what she has to say, because I feel close to her again. I feel like she wants me close to her. She wants me to touch her wherever I can.  She wants me to fuck her, whenever and wherever I can.  I feel like the effort she puts into letting me know she wants me turned on and near her, makes me try throughout the day to show her, I want to be near her. I want to live up to her appreciation. It’s more than just nudity, it’s the call of the wild. It helped  save our marriage, it helped our sex life, and it freed us from complacency.

-This article was originally written on November 4, 2012.   It was published September 30, 2013.

Diary Entry: All Kinds of Orgasms Last Night

OrgasmLast night I had the greatest sex of my entire life.  Ryan and I have all kinds of sex. It can be wild, spontaneous, slow, erotic, fierce, masochistic, and even planned out (because of our time schedules). Sometimes we orgasm, sometimes we don’t.  Last night it was a combination of all the aforementioned and ending in great, wild sex with multiple cums on my end.

Ryan’s cock was rock hard as he lay on his back, so hard that he told me to ease up on the stroking because his skin was too tight that it felt like it could rip at any time.  I loosened my grip and moved both my hands up and down the length of his shaft.  I pushed his dick down between his legs so it almost touched the bed…then released.  It slapped his stomach hard.  This was one of those times I knew when he was ready to fuck me, I would be sore the next day.  It’s happened.  It doesn’t take much.

I looked down at his dick and I wanted to put my mouth around it.  My entire mouth was full.  I had to get his head down to the back of my throat to dip into the sloppy, wet spit that I need for lubrication.  I braced myself for the hardness as I opened my throat and mouth as wide as I can to maneuver him down.  I felt like a snake unhinging its jaws to swallow an ostritch egg. From a distance, it looks like I’m convulsing in a crouched position as I work his hard cock.  It’s not as easy when Ryan’s dick is at its maximum length and thickness.  I ease down, my chin is finally touching his balls.  It rarely happens, but I gag.  He makes a kegel muscle and his dick shifts in my throat over and over again.  I can feel my air running out and I lift up slightly.  As I do, I feel his hands on the back of my head and thighs press against my ear signaling me to stay.  I submit to him and stay the extra 15 seconds.  His legs part and I gasp for air.  I replenish and repeat.

His dick is smooth and shiny now, ready to be guided past the growth of hair between my legs.  I get on top of Ryan and slowly rub his penis over my pussy.  Ryan feels the wetness between my lips that has formed from the intense deepthroating.  “Oh, my God, you’re horny aren’t you?”  I face him as I ride gently. I’m careful not to be too hasty, like I were dipping my toes into a swimming pool.  I try to rock back and forth slowly, but the top side of his shaft is rubbing hard on the back of my vagina walls.  I inch back and grind again. Still rubbing hard on the underside of my pussy AND in the back. No matter where I move to, he was too hard for me to enjoy.  But Ryan knows what to do.

He tells me to get on my stomach.  His cock has no trouble finding my little hole; they’re drawn to each other.  He’s kind enough to pump his hips slowly at first.  I moan wearily as if I’m in pain.  In fact, I am.  With each movement of his body, I lie in wait, waiting to see if the next movement will be a deep, hard push against my cervix.  Honestly, those are the ones I crave, the ones that make my toes tingle, the ones that pinch a nerve down both my legs, the ones that send a spark from my g-spot to the backs of my knees – the ones that leave me in a delicious state of paralysis.  I tell him to go deep and slow, and to hold  his dick head at the very back; that is my sweet spot, the reason I love being taken from behind when he uses all his weight, his man-strength, to make me quiver from the inside out.  I can tolerate the pain just enough to where I do NOT want him to stop; I want him to keep going.   I continue to mumble, “Go deep and slow, go deep and slow,” and he obeys.  He moves slow and methodically.  Ryan knows that when he is this hard, fucking me fast and deep is too painful. If he goes fast, the pain shocks my entire body and makes me jerk in pain.  I need it slow.  He pushes into me with enough force to move us both off the end of the bed.  I feel my nipple rings drag beneath me as my breasts are pushed flat.  We reposition ourselves back to the middle of the bed.  I grab the edges of the mattress and try to keep from moving again, flattening myself in order to stay put.

An hour or so passes. An hour of deep, hard, slow fucking.  I am hypnotized by the intense feeling building inside my pussy.  The longer he holds the push toward, the more I feel my orgasm building.  Ryan knows this.  Just then he finds the spot.  I lift up my ass to make sure he can grind his dick as hard as he can.  I tell him to keep going.  He moves faster, slamming his penis into the back of me over and over.  I’ve been put into a trance.  Soon I hear a wet smacking sound and feel juices dripping down my ass and thighs.

Ryan confirms what I am feeling and tells me, “You squirted all over me….”

I moan and reply, “I’m sorry.”

He responds by changing his pace and slowly down, grinding deep inside my wet pussy, “There’s nothing to be sorry about.”

This is a great first cum of the evening.

His rhythmic pumping slows again before he lays back down on the bed.  I go straight for what’s in between his legs and suck away. I taste my juices, which Ryan describes as smelling like watermelons and apples.  I rub my face in his soaked balls and clean between his thighs, under his balls near his ass, and around his thighs.  I clean him off until there is no trace of me.  He tells me he wants to get back inside me.  I deepthroat him again and leave the sticky spit all the way down to his balls.  I get back on my stomach and wait for him to slip into my body.  His dick is harder than ever now.  I tell him again that I want him to go deep and slow.  He digs up in me like he’s shoveling snow.  Once again I’m put in a state of paralysis as he pushes all his weight onto my cervix.    He leans around me with his face and tells me to lick the sweat off his neck and forehead.  I obey.  After all, he has worked hard pleasing me and making me cum once already.  As his cock gets even harder and his balls tighten up, signaling to me that he’s about to cum, I grab the sheets even tighter.  Nothing we ever do comes close to the intensity of a huge strong man with his penis at it’s hardest, seconds before it cums.  I scream, trying to bear the pain for just a few moments longer.  He uses his dick to skewer me as my head is now off the bed from all the jarring.  His cum is so intense, I can feel the the first shot shoot inside me.  It’s very rare, but it has definitely happened.

Then an unusual thing happens: I cum again.  My most intense cums come from when I used a Hitachi, a.k.a. “back massager.”  Why?  Because my clit is stimulated with such an intensity that I’ve been known to cum within seconds of it making contact with my body.  My body muscles begin to tighten up as soon as I get the cum feeling; the g-spot behind my clit has been activated.  Ladies, you know what I mean.  The feeling cannot be stopped and we HAVE to cum otherwise we get frustrated.  As soon as Ryan came in me, those same muscles that I tighten when I have a Hitachi cum were triggered. When his dick was still twitching inside of me, spewing out the last bit of cum, my body was numb.  All I felt was my inner pussy muscles convulsing.  I told him to keep pumping in me.  This type of “hands-free” cum has only happened to me a handful of times, pun intended.  I noticed that this only happens when HE is cumming in me.  It’s as if HIS cum triggered MY cum.  If his orgasm is short, as in he pumps just a few times, or he doesn’t press back in me long enough, I absolutely will not cum.

What a great second cum and third cum for the night.   If you missed the third, that was when Ryan released himself inside me.  I strongly believe my body or mouth making Ryan cum is equally as satisfying to me.  I love draining his body and holding his fluids for the rest of the night.  His orgasms alone satisfy me completely.

Ryan, exhausted with a sweaty body and our cum on his penis, then asks me if I want to use my toy to get a clitoral stimulated orgasm.  I KNOW for a fact I’ll cum, so why not get all four kinds of cums in one night?  I get my toy.  Ryan lays to my side, sucks on my nipples, and starts fingering my cum filled pussy.  Sometimes he will fuck me with his dick as I do this — not today.  I can feel his wet dick starting to soften on my thigh.  He scoops out our cum with his fingers and wipes them down my crack to my anus, then proceeds to stick a finger there in there too.  Two minutes pass and he says to me, “My dick can make you cum faster than this.”  Funny, because today it was true.   Soon though, my toes start to curl and I can feel the jittery sensation in my pussy.  He moves his fingers in my ass and pussy faster as he  also swirls his tongue around my nipple.  I squeeze tight around his fingers and scream out that I am going to cum. The spasms continue for another minute before finally subsiding.  I feel my body pouring onto the bed as if someone turned on a faucet between my legs.  Whether it was my orgasm or his huge load, my body drains as if I was having my own “cum shots.”   I rest for a moment before getting up to take a shower.  I look on the bed and see two dark spots where the sheet has been soaked, one where I squirted and other where my body just was.

What a great fourth cum for the night.

Although I have different ways to cum, this was the first time I had all four different types of cum feelings in one night, so I figured I would write it out for keepsake.  Also, I do not want to confuse my above blog with multiple orgasms, because for me that is a bit more common.   Mostly through clitoral stimulation, but that is a whole other topic for a whole other blog.  Most of the time, my clitoral orgasms comes in twos, if you know what I mean.