Online Dating an Adventure

My next online date was to be this attractive blonde lady named Kathy. From the pictures I could tell she had very large breasts. We had talked about playing golf, but she said her breasts were too big and got in the way. Four times we had set up a time but she had to cancel. I had a friend who has a sweat at our local pro baseball stadium. He had two extra tickets. Kathy said she could make the game. The day before the game she called me and had to cancel.

I decided I was done trying with her. In the meantime there was a lady named Donna I saw online that I was interested in and we chatted online a few times. I sent her a message about going to the game. She replied right away she would love to go.

Next day I went to pick her up. She lived in a very rich neighborhood. A lot of professional athletes live near her house. She was cute. Looked just like her picture. Shoulder length hair. Big smile. Petite frame. I figured her a C cup. Later she said she was a D. I think she was wearing the wrong size bra!

We went to the game and had a great time. We were on this kiss cam and had our first kiss in front of 36,000 people. I brought her home and got my second kiss that led to some heavier kissing.

By our 4th date we were having a heavy make out session on the couch. I got bold and moved my hand to her breast. She moaned into my mouth. I slid my hand up the back of her shirt and lightly stroked her skin. I moved my hand to the front and slid it up under her bra.

As I massaged her breast I felt her hand on my thigh making its way to my already hard cock. While massaging her breast I noticed her nipple wasn't getting hard. I was not sure if she enjoyed what I was doing. She was moaning and when her hand felt my cock she broke off our kiss and said, "Mmmmm you are really big."

"Can you spend the night?" She asked.

"Yes I can."

We went into her bedroom. There was no sexy kissing and undressing each other. Donna just started to undress in front of me. I followed her lead. She crawled under the covers. I went to turn off the lights. She said, "Leave the lights on. I don't like the dark."

I am thinking this is weird. But she was also tipsy from all the wine she had been drinking. I didn't care I was about to have sex.

I got in bed with her and she said, "Take it slow. I haven't been with a man since my husband died 15 years ago. We kissed and explored each other's bodies. I worked my way down and started to lick and suck on her dark nipples. Still no response from her nipples. Feeling a bit frustrated I moved down between her legs.

My first lick of her pussy her whole body shook. "Oh my God!" She said.

I worked my magic with my tongue. It was hard as her body was practically convulsing from pleasure. When she came she held my head tight against her pussy with her fingers grabbing my hair.

"Oh my god Brian that was amazing. I want the big cock in me. I want to feel you cum in my pussy."

I moved up and she took my cock into her hand and guided me into her pussy. I slowly tried to enter her. She seemed to be in pain. She started to say it hurt. I was too big. I only was half way in before she told me I had to pull out.

"I am sorry, I don't know what is wrong. Let me make it up to you."

With that she went right to my cock with her mouth. No teasing or anything. She deep throated me at the blind of an eye. One thing was for sure. She had skills. She sucked and licked my cock and balls. It didn't take long before I exploded 4 streams of cum into her mouth. She looked up at me and smiled then swallowed.

Donna went to the Dr. to find out what was wrong. Turned out her vaginal walls were not producing enough lubricant. He put her on medication. Told her to try again in two weeks.

During that two weeks we had oral sex and I would use my fingers to masturbate her. She had some huge orgasms from me using my fingers. The best one was I stopped giving her oral before she could come. I moved up and kissed her deeply letting her taste herself. I then slowly played with her outer lips and teased the inner lips. I would slide a finger part way in and ever so slightly rub her g spot. After doing this numerous times I started to circle her hard clit with my finger. Occasionally brushing across it. After a good half hour of this teasing I started to rub her g spot and her clit at the same time.

Her hips started to rise off the bed thrusting against my hand. She came hard saying "Fuuuuck, what the hell did you do to me?"

I kept going until she had 3 more equally strong orgasms. She pretty much passed out and I was left with an erection to take care of myself.

The day finally came for us to try intercourse again. Donna usually had a hard time sleeping. I figured well yeah, you sleep with the lights on. But to help her sleep she took Ambien. She would also mix it with her wine. She did a lot of weird stuff in the middle of the night that she didn't remember.

This was one of those nights when she had plenty of wine and took her Ambien. It was also the best night of sex with her.

We didn't wait long and we in bed by 8. I wanted to do it right. I gave her lots of 4 play. I started with deep sensual kissing. I worked my way down between her legs for oral. I wanted this to be a night for her to remember. I worked her hot pussy as best as I could until she had two orgasms. That was one of the things I enjoyed about her as she had no problem having 3 to 4 orgasms.

I figured she was ready. I moved up and put my cock to the lips of her pussy.

"Oh baby, fuck me baby, fuck me good. I want to feel your hot cum inside me.""

She really liked to talk dirty when she was drunk and high on her Ambien.

I slowly entered her. She showed a little pain but not much.

"It hurts a little but that's because you are so fucking big."

With a little effort I was finally deep inside her hot little pussy. I took it slow at first. Problem was she was so tight it felt really good and I knew I wasn't going to last long. I tried my best and we got into a good rhythm. Her fingernails started to dig into my ass. She was getting close. She came hard just as I couldn't hold back anymore. I filled her little pussy with 4 streams of my seed. I collapsed on top of her. We stayed in that position listening to our heavy breathing.

Once I caught my breath I started to get up and pull out.

"Don't get up yet. I want to feel your cock in me for a while longer. I can feel your cum leaking out me and down to my asshole. It feels wonderful."

"You can get off me now. I have something special for you now."

She moved down between my legs and started to give me one of her amazing blow jobs. She knew what I liked by my moans. She would swirl her tongue around the head. Take me deep, then just tease the head. She started to suck and lick my balls. Then she did an amazing thing. She put her tongue up my ass.

I didn't know what to think at first. But I was surprised that it felt good. She was great at multi-tasking. While she tongued my ass she stroked my cock with one hand and played with my balls with the other. The sensation was amazing.

She could tell I was getting close and her hand jerked me faster and harder. I shot several ropes of cum across my chest and stomach. But she didn't stop. She slowly masturbated. The hand she was using to massage my balls was now used to probe a finger up my ass.

"Holy Fuck, what are you doing?"

"Evil naughty laugh"

God damn if that didn't feel good having her finger and tongue working my ass. My cock just got harder than before and I already came.

Her hand never left my cock and her mouth worked my balls and ass while she finger fucked my ass. This went on for a good 10 minutes before I came. The orgasm was so intense I almost passed out. I didn't have much cum but the orgasm was the best I had with her.

The next morning I teased her a bit how naughty she was and I loved it. She asked what did I like. When I told her she denied ever doing or saying those things. She did not remember anything from that night.

I am not going to go on about anything more about our sex. She turned out to be a phony. She claimed to be a Christian. Yet she did not like Black people, Asians and poor people. She told me we are from different social classes and her friends would not accept me.

For Christmas I bought us a trip to Mexico. I was planning on breaking up with her after we got back. In the meantime a lady friend (Krista) called me and told me she had a friend that wanted to go out with me. She sent me pictures of an attractive blonde. I had desires for Krista, as she looked like a young Jessica Simpson. But she was 26 years younger than me and engaged. I told Krista her friend was out of my league.

Krista said, "No she isn't. She is a lot like you. Lots of fun and adventurous. Heck if I was single I would date you."

That gave me new confidence. Plus this new lady (Mary) was 18 years younger than me. It was two weeks before Mexico. I figured if I went on just a dinner date it's not like I was cheating on Donna. Besides I was going to break up with her.

Next day I met Mary at a Mexican restaurant. She said she loved Mexican food. Hmmm that got my wheels turning in my brain. Wish it was her coming with me.

Mary looked a little different from the picture Krista showed me. Very pretty face. Blonde hair past her shoulders. Very large breasts. Later I found out she was an E cup. She was tall at 5'9". I am 5'10". She was a little big. Not fat but big boned with a little extra weight. Still very pleasing to the eye.

We had a great dinner. Full of laughs. I told Mary, "I am sure Krista told you that I am seeing someone. I will be breaking up with her when we get back from Mexico. Would you be interested in going out again when I come back?"

"I would love too. I have an opened bottle of wine back at my place. Would you like to follow me home and help finish it?"

I told her sure. As I was following her my cell phone rang. It was Donna. She started to bitch me out about how boring I am. Her snobby friends would look down on me. How she really doesn't want to go to Mexico as she is afraid we would be killed there.

I said, "You know what? Let's just end this now. I am tired of you always complaining. You call yourself a Christian yet everybody is beneath you. Just because you go to church doesn't make you a Christian. I will find someone else to go to Mexico." I then hung up on her.

I arrived at Mary's place and when she got out of her car I told her, "Well I am single. I just broke up with Donna on the phone."

She smiled, "Good I think we can have a lot of fun."

Mary brought me into her apartment and poured us each a glass of wine. Then gave me a tour of her place. In her bedroom she had a fancy king size bed. I commented, "Nice bed!"

"It takes 3 dates before you get under those covers!"

"Well we have had 2 dates so far. One at the restaurant and one here!"

Mary laughed and said, "Guess you are only one date away."

We sat on the couch and watched tv and talked about life. Then Mary set down her wine glass and said, "How come you haven't tried to kiss me?"

"I don't kiss on the first date. I am a respectful man."

"Remember, you said this is our second date."

"You are right." I set my wine glass down. I brushed her hair back from her face with the back of my hand. I slid my hand down to the middle of her back and pulled her to me and gently kissed her lips.

We exchanged soft gentle kisses. I liked how she felt in my arms. I held our kiss a little longer and her lips parted. My tongue entered her mouth slightly. Her tongue met mine. This brought on deeper kissing. After a bit I pulled back.

"I know this is only our so called second date. It might be too early but I have to ask. Would you be interested in going to Mexico with me?"

"Brian, I would love too. We would probably have a great time. But, I am a chaperone for my daughter's choir trip to Florida that week. I can't back out."

I was disappointed but understood. I told her I should probably get going. She walked me to her door and we had our good night kiss that seemed to go on forever. Her large breasts pressed against my chest was getting me worked up as I felt my cock starting to get hard.

I pressed my cock against her and she responded by grabbing my ass and pulling me tighter against her. My left hand traveled up her side and settled on her right breast. My god it felt good. I could feel her hard nipple through her bra and shirt.

She was moaning while we kissed and grinding on my cock. I started to unbutton her shirt when she broke off our kiss.

"We have to stop. This feels too good, but I told you 3 dates before you see my bed."

"I understand, I respect you and I sure hope we have a lot more dates!"

I gave her a final kiss and left. I got on the elevator and took it to the first floor. I walked to the door leaving the building. I kept thinking how I was so lucky to find her. I wanted to kiss her a little more. I went back and got on the elevator.

I knocked on the door. I heard, "Just a minute." From the other side of the door.

When Mary opened the door she had on a white bathrobe. It was loosely tied and showed a lot of beautiful cleavage.

"Did you forget something?"

"No, I am here for my 10:30 date. That makes date number 3!"

Laughing, "Get in here silly. Let me give you a proper kiss before I send you home."

She kissed me deeply and it didn't take long for me to start getting hard. I pressed my erection against her again. She responded as she did before pulling me into her. With the grinding on each other we were doing the loose tie on her robe had come undone.

I slid my hands over her shoulders and pushed her robe off from her shoulders and it fell to the ground. She stood before me completely naked.

I took in the site of her large breasts. My god they were huge and stood at attention. The defied gravity! Her nipples were a light pink. Areolas the size of a silver dollars. The areolas were wrinkled from excitement that formed into half inch nipple sticking out. Her pussy was shaved bare except for a small strip of blonde hair that was barely visible.

Her breasts needed my attention. Before I could get started Mary looked down at the bulge in my pants and said, "I can tell you like what you see."

"I sure do." With that I lifted both of her breasts up and took one nipple into my mouth and flicked my tongue across it. I worked" both of her breasts with my mouth, tongue and hands. I wanted more.

I took her hand and led her to the couch and had her lean against the back of it. I kissed my way down her body until I got to her pussy. I could see she was already wet. Looking up at her I slid my finger across her lips. I could see her beautiful blue eyes looking down at me. I could feel the heat from her pussy on my finger. I parted her lips and slid two fingers in her. She was very wet and hot.

My tongue joined my fingers inside her love hole. I licked my way up to her clit that had popped out from its hood. When I sucked her clit into my mouth I saw her fingers dig into the back of the couch as she let out a loud "Oooooooohhh my god."

It wasn't more than 30 seconds before her body shook from her orgasm. She pulled me up to my feet and we kissed deeply sharing her love juices.

"I need you to fuck me. Let's go to my bedroom."

While she pulled down the covers I quickly undressed and got into bed next to her. She took a hold of my cock and said, "You have a very nice cock. I want you inside me now."

"Are you on birth control?"

"No. I had my tubes tide after my second child."

That is all I needed. I got on top of her in missionary and she guided me into her love tunnel. I was in heaven fucking her and watching those big boobs bounce with every stroke. I didn't want to cum to fast so I pulled out and held my cock in my hand and rubbed it against her clit. She really liked that. I could tell she was starting to get close so instead of just rubbing against her clit I stroked my cock while holding it against her clit. This got me closer to my orgasm as my balls started to pump. I entered back into her pussy and fucked her hard and fast. She came again. Four more strokes and I shot my hot cum deep inside her pussy.

I only laid on top of her for a few minutes before she said, "Get up here. I know you want to fuck my tits."

The thought had crossed my mind. I was half hard. I startled her chest as she took me into her mouth and nursed my cock back to full erection. She continued with an amazing blow job to the point I told her I was getting close.

I put my cock between those amazing globes. They were so big that just the tip of my cock would pop out as I tit fucked her. Occasionally she would lick the head as it popped out. A couple of hard thrust I my first stream of cum hit her in the face and across her eye. I pulled out between her tits and she finished me off aiming my next 3 streams onto her boobs.

She has a great sense of humor as she started to laugh and said, "Oh my god, I am blind in my eye!"

She wiped the cum from her eye and face and took a tissue from her night stand and wiped her face and the cum from her hand.

She looked down at her boobs and said, "That looks sexy." Then she lifted her breasts up and licked up some of my cum.

"All right lover, you need to go. I have to be at work early tomorrow.

I got dressed and she put on her robe. She walked me to the door and we shared a few more kisses before I left.

Next day I got a call from Krista. "Mary said she had a fun date."

I am thinking 3 dates! "Yes we had a great time."

"That's too bad she can't go to Mexico with you."

"She told you about that?"

"Yes she did. I have a thought on that. How about if I go with you?"

"Krista, I am confused. I thought you are engaged. Plus there is only one bed in the room."

"I am. But I can tell him I am going with friends. Mary even suggested I go with you knowing that we are just good friends."

"I suppose that would work. I will try to stay on my side of the bed."

"Brian, I told you I would date you if I was single. Mary told me everything about your date in detail. That just wants me to go to Mexico that much more with you. I am going to consider myself single that week."

I shall end here. I will say that when I got back from Mexico I had 12 voice mail messages from Donna telling me she now realized that she loves me and I am the only man for her. I never returned her call.

Watch for my next story called Cozumel.