Dating Site Sex - His Story

My name is Richard. I'm an eighteen-year-old high school senior. I have been having great fun trolling the dating websites for a lonely MILF that will hook up for sex. I can't believe how easy it was to start having sexy messaging with these ladies. It's like a candy shop. All types of horny ladies message with me while they play with their pussies. We trade nude pic and erotic messages. You can't see their real names but the profiles say they are housewives, professionals and one is even a teacher. Go figure. It's opened my eyes to see that women are just as horny as guys. Most guys, not me. I'm super horny. They just keep up appearances in public.

I'm not super handsome but I have my share of girlfriends and casual hookups. I'm more of a nerd than a jock. I have ADHD so I take some prescription drugs that speed up my metabolism and suppress my appetite. That keeps me a bit on the skinny side which the ladies like. My pride and joy is my good-sized dick, eight inches and thick. I'm lucky that way.

These older women love cyber-sex with me in front of their computers in their cozy homes. But, I haven't been able to get a MILF to meet me for real, skin-on-skin fucking. It's been driving me fucking crazy. They all seem so close, yet so far away.

Tonight, finally, for the first time, I'm meeting one for actual sex here in this motel room. Fuck, pinch me, it's going to be great. I've had a lot of sex with young girls but my dream is to fuck a nice looking older lady. This one is classy and very attractive. I can't wait until I'm pounding my cock into her hot MILF pussy. If I'm way too horny and physical with her, it's her fault and the fault of others who have made me wait, way too long.

Young chicks I go out with are just, mainly into blow jobs. It's the big thing. Sure, a BJ is nice but I want some horny in and out in a hot pussy. It's the natural way of the animal kingdom.

While I am waiting for her, I'll tell you how I got her to come for booty call. I'm messaging over ten women at various stages from just met to swapping nude pics. I target new ladies to the dating site, especially recently divorced or separated ones that are in their forties. I start very slow. Just a "Hi, I love your profile. You are so attractive. Take a look at my profile. I'm an eighteen-year-old high school senior who would like to chat with an attractive and intelligent lady like yourself. Could we please do that. I would greatly appreciate it." I am super polite and complimentary.

If they take the bait and many have, I go forward. The story I tell them is that I am a virgin looking to lose my cherry to an experienced, attractive woman before I go off to college. We send messages back and forth. I send pictures that are more and more revealing. First, it's just bare chest and shorts until finally I'm sending full frontals with my big dick hanging down. They love it.

Most of the women I message aren't looking to hookup. They just want the stimulation of communicating on line with a horny young guy. I'm just foreplay before they get into bed with their trusty vibrator and get off. I ask for revealing pics, just below the head since they all fear any pictures with their faces getting spread on the net. I'd say about half the ladies eventually show me some skin. They must feel obligated since they are enjoying my raunchy photos. If they don't at least start sending me bare breast shots, I drop them. It usually takes me giving them an ultimatum that I will drop them before I see some tit. That's when they send what I need. It feels good ordering them to give me a shot of their ass or their pussy and them obeying.

The lady I am seeing tonight is called LadyforaMan on the dating site. We've been messaging back and forth for a few weeks. She is very attractive with a slim toned body and tits that only have a bit of a droop. I was stunned when she messaged me back. She is a professional lady, recently divorce that has been a one-man gal for her whole adult life. She's likely looking for some sex on the wild side for once in her life and I'm the guy to do her.

After we messaged back and forth a few times, I kind of thought she might be the first MILF that I would meet for sex. Early on, she was typing that she was masturbating to my pics. She is like a bitch in heat. I bet she hasn't been laid in a long time. Within a couple of days, a new record, she sent me the first selfie of herself, neck down, in a sexy red cocktail dress with lots of cleavage. She messaged that she wasn't wearing panties on under it like I asked. She also said she had rubbed off after taking it. Fuck, did I jerk off to that pic a few times. Soon, she sent me a selfie of her tits. MILF tits are a lot different that the young girls I go out with but sexy just the same. LadyforaMan's have nice big, dark areolas and long nipples. They are nice and small but look pretty firm, my guess a 34B cup, my favorite. I can't wait to suck on those sweet titties.

She sent me more titty pictures but she never would do below the waist showing her hairy beaver. When she told me she had pubic hair, it made me crazy. All the young girls at school I date have shaved pussies. It's totally the style. On my favorite internet porn sites, I love to look at pictures of mature women with hairy pussies. That really gets me off. But LadyforaMan just wouldn't take the leap and send me the crotch shot I wanted. It drove me wild looking at her titty pic and fantasizing about her thick hairy bush out of the picture. I didn't message her for a few days wanting to get her off her high horse and send me those pussy shots. I knew she was really enjoying our horny game. During those days, she sent me many frantic messages asking where I was and what was happening. She knew what I wanted. I'd asked her many times. I waited and stayed silent.

Finally, after three nights she gave in and sent me a glorious full-body pic with her light brown beaver proudly showing. That's when I knew she would be the first attractive MILF that I would fuck. All I had to do is get her to take the next big step, to meet. I thought of a plan to get her to come to me or cut off the games we were playing. I couldn't just go on jerking off to her horny pictures, even beaver shots. I sent her this message.

"LadyforaMan, thank you for the great picture. It's been my dream to see you totally naked. You have a very attractive body and the hair on your pussy makes me crazy.

The last few days, the reason I had not contacted you was because I was with my parents, out of town, looking at a university that accepted me.

I have so bad news. As I have said, I want to lose my virginity before I go off to university. I have been messaging another lady on the dating site and she say she wants to do the honors next week. She made me promise that I can't contact or have sex with any other woman from the dating site from the time we have sex until I go off out of town to school in a few months.

I really want to thank you for our time together and wish you all the best in the future.

Yours truly,

SweetGuy18"

It was all a lie, but what the fuck? She seemed addicted to our erotic messaging. I hoped she would leap to fuck her 'virgin' young stud if she thought he was leaving with another woman.

Bingo, immediately I got a message back.

"SweetGuy18, please let me be the one to be your first sexual experience. Since we started communicating, I have developed a real fondness towards you and I think you towards me. You make me feel like a real woman. Thanks so much for that. I want to make you feel like a real man, not just in pictures but in real life, touching each other. Is that possible, my dear?"

I knew it! The horny MILF is very possessive of her 'virgin' young guy, me. I teased her with this reply;

"LadyforaMan, I already promised her. It wouldn't be nice to cancel even though you are much more sexy than she is. I like you so much. You make me feel very at ease with my sexuality. Even if we don't get together, I want to thank you for everything you've done for me. Could you send me a pic of your pussy with your legs spread real wide. That would be so nice while I think about all this and what to do."

I wanted a full crotch shot with hairy pussy lips and all. I wasn't disappointed. Back came this message with a lewd pussy shot with knees spread wide.

"SweetGuy18, here is the picture you asked for. I hope you like it. When you are deciding what to do, I want you to know that I want to lick that beautiful cock of yours and roll my tongue around the head until you moan in pleasure. You make me wet with desire. Let me be the one to show you the pleasure and exciting lust of sex."

Wow, what a horny message that was. I didn't think she had it in her. She seemed a bit shy and very proper and professional in her language and manners. She's finding her inner cougar. Oh, my god, it's going to happen. I'm going to be fucking this pretty MILF. Holy shit.

I sent this message back to seal the deal.

"LadyforaMan that picture was incredible. I knew as soon as I saw your perfect, hairy pussy that it should be the first one my cock should enter. Pinch me, I'm the luckiest guy in the world. I will call one of those motels on the number 5 highway just north of the city and book a room for Friday night. I'll message you the address and meet you there at 7:00 PM. Please wear that sexy red dress, the one in the first picture you sent me. I have been looking at that and thinking about you so much. Please wear some nice panties with some flowers on them. I'd love to keep them as a souvenir of our first night together. Let's not message until then. I don't want to have an orgasm for a couple of days so I am really horny when I am with you. I'll be thinking of you every minute until then."

I was slightly worried she would chicken out if I didn't set a time and place when she was in this erotic head-space. Back came this, that made me sure all was good;

"SweetGuy18, I will be there in the dress wearing nice panties just for you. XXOOXOXOOXOOOX"

I called the motel, booked room 214 and sent her the address and room number. Then, I jerked off to the picture of the close-up of her hair covered pussy, imagining mounting her and fucking it, hard and deep. It was the best orgasm I'd had in a long time.

THE BIG MILF FUCKING NIGHT

It's almost seven o'clock and fuck am I ever horny. My fucking cock has been hard for an hour since I got here. The motel room is perfect. It has a small table and chairs, a huge bed and a nice small sofa where we can do a little touching and groping. I've had three beers and there is another three in the minifridge. That's loosened me up a bit.

Ahhh. There's the knock. I'll open the door. Wow, she is better looking than her website photos. She steps inside and we are just staring at each other. She is wearing that amazing red dress from the dating site.

"Hi, my name's Richard, that's my real name." I give her a big smile.

"Hi, I'm Lynn and that's my real name too," She blushes and forces a small smile. It looks like she's a bit shy and nervous. I like that.

"You look fantastic Lynn. You're much more beautiful in person." She is so classy I can't believe she's here to fuck me.

She says, "Thanks. Come over here and let me give you a big hug."

We embrace. She is smaller than me. Her perfume is so sexy. I can feel my woody bump against her stomach. Wow, she feels so good. I've been waiting for this for so long. The dress has a soft satiny texture. I dip my hand blow her waist and cup a cheek of that sweet ass she sent me a photo of. She stiffens in surprise and her ass cheeks clinch. After a couple of seconds she relaxes and I give the cheek a nice squeeze.

Hey, she just grabbed my ass. What a slut. Nice, I like it.

"Wow, that feels so good, you grabbing my ass. I love it. You're so wonderful."

She looks up. "You're pretty wonderful yourself, SweetGuy18."

"Hey, I like that. Call me Sweet Guy. It's much better than Richard, at least in this room." I point over to the small sofa. "Why don't we sit?" We walk over to it. I have a brainwave. "No wait." I sit down and look up at her. "Why don't you turn around and let me take a good look at you. I've been imagining this night so much since we first met online."

She turns slowly around so I can see all of her. Her bare calves below her dress are slim and strong. I can't wait to run my hand up between her legs to her hairy pussy. Her purple high heels are so classy. Her dress is just tight enough that I can see the nice curve of her ass and hips. The slight indentation where the crack of her ass is, makes my lust rise. The skin above the shoulder-less dress is so white and perfect. She has fully turned now and her deep cleavage is just like I remember from her photos.

My cock is so hard and a bit to the side where it hurts. I adjust the big guy and I can see her eyeing the big tent in my slacks. Some of the young wenches I go with can't get my thick cock in their small pussies so we just do oral. But I'm sure, LadyforaMan will take it all in with a nice snug fit.

I pat the sofa beside me. She sits a bit away from me and then slides over to me. She's horny for it too. Wrap my arms around her and pull her too me, burying my face in her soft hair.

"Your hair smells so great. That perfume is so nice."

I'm trying to fight the urge to rip off her dress and panties and pound my cock into her. I take a few deep breaths. I kiss her neck and then force her head back and kiss all of her neck on both sides. She groans as I grab her breast, way too hard, through the satin soft fabric of her dress. She is bra-less and I can feel her hard nipple. I grab her other tit and give it a good feel while we mash our lips together in a passionate kiss. My nostrils flare with every panting breath I take.

She moans, "Yes, baby. Feel my tits."

Fuck, I thought I was doing it too strong. What a slut. "Your fucking right, I'll feel your tits and anything else I want." I grab an ass-cheek in each hand and massage them deep and hard. She's panting in lust just as hard as me.

She whispers seductively, "Why don't we get undressed Richard?"

I don't know why, but that pisses me off. I'm in fucking control here. "I'll tell YOU when it's time to fucking get undressed." I tap my pointed finger in a naked spot on her chest above her cleavage. "Get it?"

"Yes, I'm sorry. Sure, whenever you want." Fuck, I can't believe she is so submissive. Who would have thunk it? I expected her to have a strong character like my mom and the teachers at my high school. Maybe all these women get all girlie when they are horny. But if they want a strong guy, I'll be that guy. You bet, my sexy MILF, whatever I want. And I know what I want.

"Well, what I want is for you to get down on the floor between my knees, pull out my cock and give me that blow job you promised."

She obediently scrambles down to the floor between my knees. Holy fuck she is going to do it. I lay back with my hands clasped behind my neck. That's my favorite position for a blow job. I love watching a wench unbuckle my belt and pants and fish my cock out of my underwear. I love the look on their faces when they see my big dick. Yes lady, open those pants. Wow, just like I thought, there's the worried look on her face when she sees it. My god, she looks a bit like my mom's foxy looking, best friend.

"Why don't you take my pants right off." She strips them down and off. "The socks too lady." There they go too. I take of my shirt to get totally nude. I love being in the buff while she is fully dressed. It's so fucking erotic.

"Okay, I remember you said in your message that you'd lick my cock and swirl your tongue around the head. Well, there it is."

She gets up on her knees and licks my dick from the base to the tip a few times. Then she sucks my nob a bit. It's nice and all but not nearly as good as the young expert teen cocksuckers I hang out with.

She is looking way too normal, all dressed up. "Let's look at those tits you were showing off on the internet." I lean forward and pull the top of her shoulder-less dress down and her tits pop out over the top. Now that looks like the horny MILF she is. I cup them and massage them. "Yes, LadyforaMan, they are even better than I thought. Nice." She blushes from her face down to her chest as I knead them and stare.

I'm realizing that this horny MILF doesn't have a lot of sexual experience other than with her pencil dick ex. I like playing with her, so I pull her forward onto my knee and reach over her ass and pull her dress up showing her sexy red panties. I take a big handful of ass.

"Wow, there's the ass I've been jerking off to." I grab the other cheek and give it a good squeeze too. "Good for you lady. You've kept your ass nice and tight. Very sexy." Now I'm hot to see her body and that hairy pussy.

"Stand up. Now's the time to take off that sexy dress."

She shimmies out of it like any tart I've fucked. What a nice strip show. Now she's only in the sexiest panties I have ever seen. They are bright red with the flowers on the waistband like I asked for. But, wonder of fucking wonders, the crotch is a mesh that you can see through and there is that thick pubic bush of my dreams.

"I love the small flowers, just like I asked. You are so good."

I lean forward and grasp the waistband with both hands and slowly peel the panties down to her thighs, revealing that thick, light brown bush. I can just faintly see the camel-toe notch of her pussy through the thick hair. I move my face closer to her crotch and the smell of pussy is overwhelming, much stronger than the young girls I date.

I inhale deeply and sigh, "Ahhh, gotta love the sweet smell of pussy."

The horny bitch grabs my head and pushes my face to her crotch. My nose is in deep, just below the camel-toe. She bends and strips off her panties with one hand while pressing my head into her womanhood. Fuck she is so in heat.

She backs off and takes my hand and firmly pulls me to the bed. Whew, is she ever wanting to get laid. She pushes me down onto the bed and climbs in too.

"You lusty, lusty lady. So, you want a good fucking." I love talking dirty to this older lady.

"Yes, Richard, I want a good fuck just as much as you. I know you're not a virgin. Let's see what you got." Holy shit, I've awakened her lust. She's scaring me a bit.

She pulls my body to hers and forces my lips to her nipples. I suck them, just like she wants. They are long and hard as diamonds. I suck them deep into my mouth and roll my tongue around the nipples. She moans with pleasure. I go to the other breast and do the same.

I remember the hairy bush that I have been dreaming of stroking. I slide my hand down over her stomach and run my fingers through her silky-soft beaver. Fuck, does that ever feel fucking great. I stroke the hair and take a small handful and give it a little tug. So sweet.

She spreads her legs wide, silently begging me to stroke her pussy. You horny bitch. Sure, LadyforaMan, I'll go down to your hot MILF pussy I've been dreaming about and jerking off to. I slide my hand over her mons and run my hand over her down covered pussy lips. She moans loudly in approval. Lower down near her vagina, the lips are drenched, soaking wet. Yes, this lady is in heat. I roll the tip of my index finger around her engorged clit. She almost screams with passion. Holy fuck, she is a real tiger.

I insert two fingers into her wet, hot love canal. Surprise, it's a snug fit for my fingers, just a bit looser that my young girlfriends. Her husband must have been a pencil-dick. I'll enjoy opening this pussy up like it's never been filled. I push my fingers in slowly and withdraw them just as slowly as she pants and moans continuously. I repeat. Fuck, none of the young bitches I go out with sound this horny. It's music to my ears.