Online Dating an Adventure

I had become a widower 4 years ago. I probably started to date to early. However, I was lonely and depressed. I have a large home and living by myself it made me feel very empty. I started to drink too much to drown my sorrows. A friend suggested I start to date. After being married 28 years I felt out of the loop on the dating scene. My friend (female) helped me set up a profile on a couple of dating sites.

I thought I could write a book on some of the weird dates I have had. But I decided to write a few short stories on the dates that included sex.

I am 55 years old. I look a lot younger. Most guess I am in my early 40's. I am 6' and 195 lbs. I keep myself in fairly good shape. I can run a mile if I had too! I go to the gym 2 or 3 times a week. Women tell me I am very handsome. I take it with a grain of salt because growing up I was the skinny geek. I am happy I changed but I don't act like I am anything special.

My first day after my friend post my profile I had 23 messages. I will admit, I was looking for physical attraction first. It didn't take long before I narrowed it down to one lady. Danna. Danna had a cute smile, bright blue eyes, black hair, about 5' 3" and a nice figure.

I replied to her message about things we had in common. She replied within a few minutes about meeting up. We decided to meet at a bar near her on Tuesday.

Wednesday:

I arrive a few minutes early. She is already sitting at the bar with a cocktail in front of her. She is cute and looks just like her pictures. Later I find that most women post pictures from 10 years ago!

I introduce myself and we enjoy a nice hug. Conversation was enjoyable. We talked about family, hobbies and found out we both like cribbage. She had a fun bubbly personality. She had the personality of a person who doesn't mind touching as she touched my hand, knee and arm. I didn't mind.

We had an appetizers' and 3 drinks each. We decided to call it a night and get together Thursday at her place. I like to cook so I told her I would make my walnut chicken dinner for her.

I walk her to her car and as we face each other she smiles at me. Her eyes sparkle and she says, "You are such a nice man. Thank you for the date."

She leans in and we kiss. Our kisses turn to several light kisses. I pull her into me and now we are kissing more passionate. Her lips parted. Our tongues gently touched. Every nerve ending of my body was exploding. I missed having any intimacy. Her tongue now entered deeply into my mouth. God it felt good and I could feel myself starting to get hard.

But as quickly it started it ended. We broke our kiss and I said, "I am looking forward to seeing you Thursday night.

Danna replied, "Me too, and by the way, I am going to kick your ass in cribbage."

I laughed and said, "We shall see about that."

Thursday:

Danna had sent me a text saying she wanted to buy the food since I was cooking. I gave her the shopping list. I arrived and she looked as cute as I remembered her and she greeted me with a light kiss on the lips.

Danna helped me make dinner. While cooking we enjoyed a couple of glasses of wine, a few kisses and she squeezed my butt a few times. I liked her playfulness.

Dinner was a hit. She loved my meal. We cleaned up and moved to the living room with our drinks and sat down for some cribbage. She bragged how good she was and how men get mad when she beats them.

I let her brag and didn't let on that I was a card shard shark. I was playing bridge at the age of 9 and picked up strategies of mine own at an early age. If I wanted I could also stack the deck while shuffling. But I would do that only for card tricks.

First two games I beat her. Third game I skunked her (that's a big win).

Danna looked at me and said, "Wow you kicked my ass."

"One thing I learned is not to brag. You never know who you may run up against."

She laughed and said, "Lesson learned. How about we watch some tv."

We found a show to watch and it wasn't long before we started to kiss. As it was on our first date the kisses started to turn hot and passionate. I couldn't control my emotions and body as I could feel myself getting hard as with each pump of my heart I could fill my cock growing and pressing against my jeans.

My left hand moved to her right breast. She moaned softly and didn't stop me. I was now in overdrive. I craved the intimacy. I wanted her so bad, but I didn't want to scare her off by being over aggressive.

We continued to kiss with me massaging her right breast. Through her shirt and bra I could feel her hard nipple. I undid the top two buttons of her shirt and slipped my finger inside her bra and brushed my finger across her nipple.

She moaned into my mouth as we kissed deeply. I felt her hand move to my thigh, stopping just below my now fully hard cock. My cock was twitching, aching for her to touch me there.

I moved my kisses down to her neck. Kissing and nibbling along the way until I got to the top of her breast. I undid two more buttons and moved the cup of her bra down revealing her right breast.

Funny how the newest of a woman is so exciting. She was a nice size B cup. I was surprised by how large her areolas were. They were a dark brown and her nipple was erect and wanting me to suck them. My tongue flicked across her nipple a few times before I sucked it into my mouth. Danna started to moan. Her hand was rubbing my thigh but was not touching my cock.

I couldn't take it anymore. My pants were already showing wetness from pre-cum. I reached down and took her hand and moved it to my cock. Her hand gripped my cock and moved along the length. She felt it for all of 10 seconds before she broke away from me and looked down at my crotch.

"Oh my God, you are huge" She continued to run her hand along my cock and balls.

"I can't believe I am going to say this. This is only our second date. But I want to see that big cock of yours."

"What do you want to do?"

"Let's go to my bedroom."

She took my hand and I followed her to the bedroom. Once in her room she took off my shirt. Undid my pants and pulled my pants and boxers down to the floor. I stepped out of my pants. She was on her knees holding my cock and stroking it.

"My god it's so big and thick. I have never seen a cock this big."

By now I was starting to feel a bit embarrassed but still was enjoying her touch. I know I am bigger than normal but the way she was caring on I figured she must have been with all small dick guys!

"Go lay down on the bed. I will be right back."

I was laying on the bed and a few minutes later she came back in dressed in a teddy caring a jar of cream.

We kissed for a bit and I pulled her teddy top down for me to play with her sexy little breasts. She told me to lay back as she was going to take care of me.

Danna got between my legs and started to play with my cock gently. By now more pre-cum was coming from the tip of my cock. She took it with her fingers and spread it along the shaft of my cock. She leaned forward and took the tip of my cock into her mouth. The warmth made the head of my cock swell in her mouth. She moved her mouth down a bit the shaft then there was a pop as it came out of her mouth.

"There is no fucking way I can anymore of that in my mouth."

She then took out her jar and told me it was coconut oil and it's good for the skin. Danna starts rubbing it all over my cock and sack while slowly masturbating me. I can feel the pre cum sliding down my dick. I know I won't last long as it has been some time since being with a woman.

Danna put the lotion to the side and started to concentrate on just giving me a wonderful hand job. In a matter of 2 minutes I felt my balls move up close to the body and ready to blow my seed. My first rope of seed landed on my stomach and chest. Danna switched to where she cupped my balls and with one finger on the same hand slid a finger up my ass. I was surprised how easy her finger slid in me. She continued to stroke my cock but directed the head towards her.

This new and unusual feeling of her finger up my ass was excitement overload and I shot 4 long ropes of cum all over Danna's chest. She stoked me like a jack hammer getting me to cum 3 smaller pools of cum.

Danna took her hand and wiped the cum all over her chest, breasts and stomach. She seemed to revel in the feeling of my warm cum on her body.

"Wow, that was so fucking hot."

"I don't think I have cum like that since I was in my 20's" I laughed.

"I want to try to fuck that big cock of your."

I was still hard and I could still feel her finger inside me and massaging my prostate. She leaned over and took the tip of my cock into her mouth and swirled her tongue around the head. "MMMMMM" I moaned.

From out of nowhere Danna produced a condom and rolled it onto my cock. She moved up to straddle me then guided my throbbing cock into her hot wet pussy that was begging to be filled.

I noticed her wince a couple of times as she lowered herself onto me. Once she was comfortable I pulled her down towards me and kissed her deeply. I moved my mouth to her hard nipples. I noticed they tasted salty and had a coconut flavor. I then realized the taste was from my cum and the lotion she put on me. I didn't care. I was enjoying this cute little horny MILF.

Danna started to ride me with more vigor as she became more comfortable with my cock. I began to thrust into her to match her rhythm. I reached up with one hand and massaged her breast and nipple. The other hand I rubbed her clit with my thumb. She really seemed to being close to having an orgasm when she suddenly rolled off of me.

"Let's try a different position."

"Ok, I like doggy style."

She agreed. I entered her tight little pussy from behind. I looked over at her bedroom vanity mirror. Damn that was a sexy sight. Her on her hands and knees with her boobs hanging down with her nipples still hard. Me being deep in her pussy, sliding in and out.

I grabbed her narrow hips and started to thrust harder and faster into her. I came so much from before I knew it would be awhile before I could cum again. I pounded away hard and as fast as I could for a good 15 minutes. But I couldn't get myself to cum again. Plus she had not had an orgasm either.

Danna looked back at me and said, "This feels really good, but the only way I ever have an orgasm is from missionary position."

We switched to missionary and after a bit I knew I was finally getting close and could tell she was too. I lifted one leg over my shoulder and went as hard and fast as I could. She came first with an "Ooooooohhh fuck yesssssss."

I wasn't far behind her with a couple of grunts and hard pushes I filled the condom.

I rolled off her. We were both dripping wet from our vigorous activity. I felt my eyes start to fill up with tears and then a couple of tears roll down the side of my face. I missed companionship.

I brushed away the tears before Danna could see them. She moved over and put her head on my shoulder and ran her hand through my chest hairs.

She then asked me, "What fantasy would you like to do that you have never done?"

I thought a bit then said, "I have never done anal and wouldn't mind trying it."

She looked at me surprised. Then said, "Well I don't know about that. But I am bisexual and we could to a 3 some with another woman."

"I have done that several times before, but I am willing to do it again!"

We visited a little bit in bed then I told her I needed to head home as I have to be at work in the morning.

The next couple of day's things got weird. She started to send me links to houses for sale near me. She was saying she could buy one of these houses so we could be closer together. Then a few days later she tells me I need to go out with more women. I need to know what's out there. She thanked me for the good time.

Two weeks go by and I get a text from her. Her niece is getting married. She doesn't want to go to the wedding alone. She asked if I would go with her just so she can have someone to dance with and not be lonely.

I agreed. Turned out I could go to the reception but not the wedding. No big deal for me. I get there and she is parading me around holding onto me and introducing me to people like we have been dating for years.

I had a few drinks and we had fun dancing. The reception was at a high end hotel. She asked me, "Why aren't you drinking very much?"

"Because I have a long drive home tonight."

"You don't have to drive home. I booked us the Presidential Suite. I had it stocked with wine and champagne for us. But don't worry, I won't attack you. It's that time of the month."

I agreed to stay and after a bit we decided to head to our room. We get to the room and she tells me to poor us some champagne while she changes.

She comes out in a lacy teddy and the top is sheer and I can see her nipples are already hard. I don't say anything. We sit on the couch and turn on the tv more as background noise and visit for a bit. Two glasses of champagne later we decide to call it a night.

We get into bed and she cuddles up next to me. Then said, "Can I have a goodnight kiss?"

"Sure" I reply.

She leans over the top of my and begins to kiss me. I can feel her hard nipples against my chest. I start to get hard. Her hand slides down and frees my cock from my boxers and starts to stroke me.

She breaks from our embrace and gets out of the bed and comes back with her purse. She pulls from her purse a jar of Vaseline and condoms.

"What's up with that?" I ask.

"You said you wanted to try anal. So do I."

I wasn't sure all what needed to be done but I gave it my best try. I put the rubber on and lubed my cock up with the Vaseline. Danna got on all 4 ours on the bed and I put the tip of my cock at her brown star.

I started to push. Danna looked back and said, "I think you need to loosen me up with a finger or two first."

I put Vaseline on my middle and index finger. I slowly slid in my middle finger and finger fucked her ass for a bit. I inserted a second finger. She moaned and said, "That feels gooood."

My cock was pulsating and it needed some attention. I pulled out my fingers and tried my cock again. With a little bit of effort I got the head of my cock in her.

"Oh fuck, you are big. I don't think I can do this."

I couldn't stop, I pushed harder. I was now ¼ of the way in.

"Ok ok keep going just take it slow."

I was too horny to go slow. I pushed and got half my cock in her. She collapsed on the bed. Falling on top of her I drove in another inch or so. She was so tight and I have to admit, it felt great. I figured I was deep enough and started to slowly pump my cock in short strokes. I was pretty sure I wasn't going to last long.

"Ow, ow, ow" she cried. "I can't do this. Take it out."

I pulled my cock out of her tight ass wishing she would have given me 15 more seconds of pleasure.

"Well we tried. Put that nice cock in my wet pussy."

"I am sorry, I can't do it when you have your period."

She laughed, "I lied about that."

That night we used every condom she brought as we fucked in every position we could think of. We went to sleep at 4 a.m.

I woke up at 7 a.m. and told her I had to get home. I had to get home and let my dogs outside since I didn't arrange for someone to take care of them.

She kissed me and said "I am going back to sleep. You take care of that beautiful cock of yours and go make other woman as happy as you made me."

I left and never heard from her again.