Dating Site Sex


I can’t believe I am going to a motel to meet a young man for sex. That’s just not like me. He’s only eighteen and I’m forty-two. But I can’t stop. I’ve fantasized about this for so long and it has become an obsession I must fulfil. Whatever the consequences, I must go through with it or I’ll go bonkers.

It started a few weeks ago, I had been on a dating website for about a month looking for a relationship with a man my age. My online name was LadyforaMan. My profile describes me just as I am, a slim, attractive professional lady with two early teenage kids and normal hobbies. The photos I put on there were tame, mostly head shots. My marriage had ended in divorce. I spent six months grieving the loss but thought it was time to date. I had never been with any man other than my ex-husband. We met in college. Several nice men contacted me on the dating website and I had a lunch date with one. He wasn’t a good match so we didn’t go further.

Another man name George and I corresponded on the site several times before we went out for dinner. He also didn’t seem right although he was very sexy. I hadn’t had sex for so long that even getting ready to go out on the date made me very horny. My private parts were wet and throbbing throughout the dinner. When I got home, I paid the babysitter and almost ran to the bedroom, stripped off my dress and panties, got out my trusty vibrator and brought myself to a huge orgasm in no time. I toyed with the idea of dating George for casual sex but he had made it clear that he was only looking for a long-term relationship. It wouldn’t be fair to lead him on.

That night I couldn’t sleep so I went to the computer to check on my dating site messages. There were a lot of messages from young men, way too young for me. This is so common on dating websites. My girlfriend warned me about this. These boys want to hook up for sex with older, experienced ladies they call MILFs. I normally ignore them but likely because I was in a horny mood, I read a few of them.

One caught my fancy. It was from a nice looking eighteen-year-old high-school senior. He had a very polite message that talked a bit about his hopes and dreams. He was a virgin that always dreamed of losing his virginity to a beautiful experienced lady like myself. I don’t know what possessed me, likely the horny mood I was in, but I sent him a message, nothing outrageous, just a ‘Hi, how are you.’ type of thing. I must admit I was stroking my pussy with my left hand while I pecked the keyboard with my right index finger. I kept thinking, “Girl, you need to get laid.” Messaging an eighteen-year-old was just a tease because nothing could go anywhere. A woman is allowed a harmless flirtation.

He must have been up, because he immediately sent me back a message. His site name was SweetGuy18, and he was so sweet. He wrote about how attractive he thought I was and how he had read my profile and thought I was such a great person. I looked at his profile. He was more of a nerd than a jock. One picture was very hot. It was him at the beach in his swimming trunks. He had a lean body and his swimsuit had a nice bulge. I couldn’t help myself. I started strumming my pussy until I had a quick, surprise, screaming orgasm. I thought I would wake the kids. That was the first time in years that I got off without my vibrator. Later, there was a big wet spot on the fabric seat of the chair. After that, I remembered to put a towel down before contacting him again.

The next couple days, I couldn’t stop thinking about him. I was like an animal in heat. Going out with a boy half my age was so bad and I fought the urge. I knew I badly needed some sex. I toyed with going out to some pickup bar on the other side of town and getting laid. But that seemed too dangerous and not my style. Maybe, I thought, call up a male escort to get some relief but that didn’t seem right either. I just hoped I would find a good man on the website, my age as soon as possible that would fill my needs in a mature, dignified manner. Meanwhile I could have sexy, anonymous cyber-sex with a young stud. I was not planning any sort of rendezvous.

My messaging with SweetGuy18 was getting hotter. He talked about touching himself while looking at my picture. I admitted the same. Why not I thought, I’ll never meet him. He sent me some pictures on the internal site mail system. At first, they were just bare-chested in shorts or sweats but each day they got more revealing. Soon is was underwear shots and finally full frontal showing his very nice looking penis hanging down. I saved them on my hard drive. He was making me crazy with lust. I never gave oral sex with my husband but my mouth watered at the sight of SweeyGuy’s young penis. I knew that oral sex was all the rage nowadays and I thought I must really try it with the future older man I will meet.

SweetGuy18 begged me for selfies. I resisted because I didn’t want my identity known. He said he just wanted a neck down shot of me in a nice dress. My photos on the dating site were all portraits. Why not? I was enjoying his naked pics. I should return the favor with a much tamer Mardin Escort one for his enjoyment. I went to the big mirror in my bedroom, got dressed in a shoulder-less red, cocktail dress with a lot of cleavage showing and shot the picture. I had no panties on underneath just like he asked. That made me feel really naughty. As soon as I finished taking it, I fell back on the bed and stroked my pussy and came almost immediately. I uploaded it to the website and attached it to a message to SweetGuy18.

“Here you go, SweetGuy, me in my sexy dress with no panties on underneath. I must confess that I have been pleasuring myself while looking at the naked pictures of yourself you sent me. I hope you will find pleasure in this photo too. My pussy was so wet when I was taking the photo. You make me so naughty and horny.”

“LadyforaMan, you look so great in that red dress. It is soooooo sexy. Your body is so beautiful. Any man would be so lucky to be with you. I am stroking my cock as I type this, looking at your perfect picture. Your breasts look so delicious spilling over the top of your dress and your skin is so perfect. I wish I could touch your soft skin and smell your sweet feminine odor as I kiss your shoulder. Oh, my frigging god, I just had an amazing orgasm. Jeez, wow, that was incredible. Thank you, thank you.”

He sent me back a picture with his big erection in his cum-covered hand sitting in front of his computer monitor with my picture on it. He begged for more pics. The next night I sent him a picture of me bending over revealing deep down my loose, white blouse with my bra-less breasts showing almost to but not quite showing my nipples.

He begged for more. I couldn’t resist. The next night, I gave him a picture of my bare breasts. I was careful not to show my face but you could see the bright pink blush down my neck to my chest from embarrassment. My nipples were as hard as diamonds. My god, that was so sexy. None on my friends would ever believe I could do that. But who could ever find out? I bought a six pack of double D batteries for my vibrator and used them. I couldn’t remember sex being this hot even though it was solo.

Every night when I got home, I would go to my home office as soon as I could and check for messages. When he didn’t message me for two days, I was concerned and took the leap to send him a standing full length nude picture with my hairy pussy showing and all. In the past, when he begged for a full view, he always said he wished I had a natural beaver. That was his fantasy. Fortunately, I trim my pubic hair but never shaved it off. I guess I am old-style with that. He messaged me back immediately, thanking me over and over. He loved my light brown bush and said he’d love to run his fingers through the silky thatch.

SweetGuy18 said he’d been out of town with his folks looking at a university campus that had accepted him. He said he really wanted to lose his virginity before he went to university. Then he dropped a bombshell. He said he was in contact with another mature lady on the website that was going to see him the next week to do the honors. She had made him promise that he would only be with her after they had sex until he left for university in a few months. I was devastated. I was losing my young man to some hussy. This thing we had made me feel alive and sexy. What was I to do? Of course, I would have to be the one to take his virginity not some scraggy bitch. He was mine. I sent him a message.

“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?”

“LadyforaMan, I already promised her. It wouldn’t be nice to cancel even though you are much sexier 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 was just in my nightie and my cell was on the computer table so I quickly laid on the carpet and spread my legs and took several pictures. I was a frantic and a bit shaky. The first ones were too dark so I put a lamp on the floor by my knee and the next ones were very clear. I even spread my pussy lips a bit to show some of the pink of my vagina. It was glossy wet with my juices. I uploaded the best one and attached it to a new message. I needed to make him want to choose me. I’d do anything.

“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.”

At Mardin Escort Bayan that moment, I was desperate to make him choose me. I was a cougar in heat and literally panting with lust. If he was there at that moment, I would have ripped his clothes off and done him on the floor. It was almost like I was not the old me but some primitive, sexual being with strong, irresistible, primitive needs. I’d come so far in a short time.

Ten minutes later, back came a message.

“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 book a motel room and message you the address and room number. We’ll meet 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 must say, he had become bolder but I still sensed that he was still a sweet guy like his web name said.

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

The next two days before the big night were hell in anticipation. I went to a lingerie shop and spent an hour or more searching for the ideal pair of panties. They had to be ones that a man would keep for life remembering the big day he lost his virginity. I finally decided on a deep red lace pair of the Brazilian style with a broad band at the top with a see-through mesh at the crotch. I wanted him to see the pubic hair he fantasized about and think about it in the future. The waistband was covered with pink embroidered flowers like he asked with a small, pink silk bow in the centered below my navel.

Tonight is the night. I had my hair done at the salon this afternoon. I got a cut that’s the fashion for younger women. This was followed with a manicure. I got a flaming red color polish that would go well with the red dress and panties. Dark purple high heels and purse completed to outfit. I showered and trimmed some of the wild pubic hair so that it was still nice and long but groomed. I shaved the hair around my anus and up to the bottom of my pussy lips. It wouldn’t be good to gross out an inexperience young man with hair in nasty places. I left the down covered lips of my pussy untouched for his pleasure. As I was working on my crotch, I would occasionally stroke my womanhood from camel-toe notch to vagina and feel the tingle of sexual energy swirl under my palm. It was crazy making.

After dressing, I spray a good amount of perfume on my neck and wrists. It made me feel completely foxy and ready for love making.

The babysitter came and as night was falling I drove over to the motel.

It’s time. My heart is beating out of my chest as I climb the flight of stairs in my heels to the second floor. I should be the one in control since it’s his first time. That seemed easy when I was in my house in front of my computer. But, I’ve always been a bit submissive when it comes to men. I’ll do my best. What happens, happens.

I knock softly on the door to 214. I feel like a total harlot, a mature woman meeting a young man half her age for sex. What would my mother think? Fuck it. I need this.

The door opens and it is him. He’s taller than I expected, maybe a little over six feet, at least six inches taller than me. His blonde hair is cut short. He’s wearing a nice patterned, buttoned shirt and tan slacks. He’s much more handsome than in his pictures, but it’s him, a normal, nice looking young man. I stand there holding my purse with both hands in front of my crotch. I’m lost for words. The motel room behind him is large with a small sofa, a table with three chairs and a large bed.

He breaks the silence, “Hi I’m Richard. That’s my real name.”

I reply, “I’m Lynn. That’s my real name too.” He smiles a big smile. I try to do the same.

“You look fantastic Lynn. You’re much more beautiful in person.”

I try to take a bit of control. “Thanks. Come over here and let me give you a big hug.”

I open my arms with my small purse in one hand and he steps forward. We hug. His body is lean and strong. I put my head against his chest. His heart is beating strongly. He smells of manly soap.

I give a girlie little squeal when his hand dips down and cups the cheek of my ass. I didn’t expect that. I have an instant urge to grab his hand and scold him but I quickly realize we are here for sex. He isn’t some stranger who has taken liberties. But of course, he must be really horny sitting here waiting. It’s natural that he has been thinking all these nights of touching my private areas and now I’m here. To stay with the program, I drop my free hand to his ass and give it a good squeeze.

He sighs and says, “Wow, that Escort Mardin feels so good, you grabbing my ass. I love it. You’re so wonderful.”

I look 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.” He points to the small sofa. “Why don’t we sit?” We walk over to it. “No wait.” He sits down and looks up at me. “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.”

I turn slowly as he ogles my body up and down with a hungry look in his eyes.

“Sweet Lynn. Yes, really sweet. Wow, you are sexy. I love that dress.” I can hear his heavy breathing and feel his gaze on my ass and bare legs even though I was turned away from him. When I slowly turn back to face him, he brazenly adjusts his penis in his slacks. I can feel my lust starting to stir.

He pats the sofa seat next to him and I sit down knowing that we are now on the slippery slope to fucking. The outside world melts away and it seems like we are enclosed in a secret, primal envelope of space and time. My senses seem heightened as I sit less than an arms-length from Richard. I can hear the swish of my legs rubbing together as I sit, the smell of the faux-leather sofa and the light blonde hair on the back of his hand. He seems so big and strong beside me. That seems right.

I decide to try to gain some control and shift over to his side to make the first move. He turns and pulls me firmly to his body. He buries his face in my hair.

“Your hair smells so great. That perfume is so nice.” It seems he likes to be calling the shots. Oh well. He pushes my hair back from my neck and kisses me in the sensitive area under my ear. That feel so good. He dips his head under my chin and I am looking up at the ceiling while he kisses me aggressively from one side of my neck to the other. At first, I’m surprised but then my libido kicks up a few notches. I hold on to him as his lust rises.

He pulls his head back and kisses me on the lips in a fury. I grab his head and pull his lips to mine. Our tongues swirl together in an incredible French kiss. I am being swept away. He feels my breast roughly through my dress. God, that feels great. I bring my other hand to the back of his head to give him total access to my body. He paws at my other breast. I dimly remember this kind of sexual lust back in my college days with my ex. It feels so refreshing and alive.

“Yes, baby. Feel my tits.”

“Your fucking right I’ll feel your tits and anything else I want.”

Richard doesn’t seem to be a shy virgin I thought he would be. But this is better.

He reaches down with both hands and grabs an ass-cheek in each. He massages them deeply as he makes deep, animal sounds in his throat.

“Fuck, I have so wanted to feel your MILF ass for so long. I’ve dreamt of this. It is so sweet. Ummmmm.”

My pussy was instantly on fire as he massaged my ass. I realize I’m panting with lust and my nostrils flare with every breath. I’m feeling constrained by my clothing and need them off to go skin on skin.

I whisper in his ear, “Why don’t we get undressed Richard?”

He looks me in the eyes angrily, “I’ll tell YOU when it’s time to fucking get undressed.” He taps his pointed finger in a naked spot on my chest above my cleavage. Firmly, not painfully. “Get it?”

“Yes, I’m sorry. Sure, whenever you want.” I am a bit worried. It’s likely just the lust of a sweet boy talking, I tell myself. I wanted a good fucking and here is the male energy that is going to mount me and fuck me good.

“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.”

Okay, right, I think and scramble down into position. He is sitting back with his hands clasped behind his neck with a big shit-ass grin on his face. I look at the tent in his slacks and go upright on my knees, reach his belt buckle and undo it. His zipper is next and the front of his pants part. His blue underwear has a wet spot at the tip of his erect penis underneath. I pull down his underwear and his naked staff pops into view. It’s much larger than my husband’s. Holy shit I think, this is going to be one memorable fuck.

“Why don’t you take my pants right off.” I pull everything down and off. “The socks too lady.” I strip them off. He unbuttons his shirt and tosses it to the floor beside the sofa. It feels so strange to be fully clothed while this young man is now totally nude. “Okay, I remember you said that you’d lick my cock and swirl your tongue around the head. There it is.”

I get high on my knees again and close in on his circumcised weapon which is pointing back. His legs are spread and his hairy ball-sack is hanging low. I reach to the other side of this pole and point it straight up. I lick from the base to the underside of the head. He moans in pleasure. I repeat the licking a few more times as he moans continually. His cock feels like satin over granite. I cup his balls to heighten his pleasure. I’d read that in Cosmo a few years ago. I go higher with my lips and engulf the big, crimson head and swirl my tongue around it the best I can. I go slowly so he won’t cum too quickly. Young men can cum prematurely and I want this cock inside me.