BBW Encounters Ch. 01

Chapter 01 - Annie

A friend asked me recently, "Why do like big beautiful women, what's the attraction?"

The question made me think, "Why do I?"

I guess the answer is that I have always been attracted to women with lots of curves and my sexual experiences just made that attraction stronger. It made me think back over the years to plus size ladies I have known and loved. It made me think first of Annie Livingstone.

Annie and I had known each other forever, growing up on the same street in a small town. Our parents were friends and naturally we played together when we were little and our families often took shared vacations, camping in the mountains or at the seashore.

We continued to be good friends right through high school, and when we headed off to college, we ended up sharing accommodations in a basement suite at Annie's cousin's house.

Annie and I were best friends, but growing up together we had not had any boyfriend/girlfriend relationship.

Now Annie was what some might describe as a "cute chubby girl". She was one of those people that had a smile that warmed any room she entered and she had a friendly outgoing personality.

She had not had any boyfriends that I could remember through high school as she was, like me, considered a bit nerdy by all the "cool" kids. We were both A students but we both had to work hard to achieve the high grades. We often partnered up on projects for various classes. Me, I was a bit skinny and gangly during high school. I liked to run, but was not involved in any team sports. Like Annie, my dating during high school was pretty much zilch.

Now I guess you could describe me as a "tit man" because I always had an eye for girls with big breasts, and Annie sure fit that category. Living together in the basement suite made me notice her body more. She often wore a sweat shirt and when she moved around, you could see her breasts sway under the material. I was pretty sure she never wore a bra when lounging around the suite with her sweat shirt and baggy pants. As time went on, I started really noticing her and I guess becoming attracted. I think she knew, because often she would make a point of bending over near me so I could peek down her top and see the tops of her big breasts. She also would bend over when I was around, seeming to pick something up, but making a point of letting me see the sexy shape of her round bottom.

Our bed rooms were side by side and sometimes I would hear sounds coming from her room at night that I first thought were sobs. I wondered why she was crying as she seemed happy enough all day, but then she was sobbing at night. I came to realize that she was not sobbing, but panting and I just knew she was masturbating and having an orgasm. Once I figured it out, those sounds became a real turn on and I began stroking myself as I listened.

I guess it was about 3 months after we moved in that Annie and I were sharing a bottle of cheap wine and out of the blue she looked at me with her big brown eyes and said, "We should have sex!"

I almost choked on my drink and am sure I turned beet red. Not sure what to say, I stammered, "Pardon me." Annie calmly replied, "Look, we both have needs and frankly I am tired of having sex by myself!"

I smiled and stammered, "Ya, me too!"

Annie told me that she knew I had been checking out her body and that she didn't mind. She was glad I was attracted to her.

With that she quickly pulled off her old sweat shirt and I was staring at those big gorgeous breasts of hers. They were all I had imagined, big and round with dark tips and nice fat nipples. I gasped and was a bit speechless. Annie, who probably had been planning this for awhile, kept talking. "I'm not talking about intercourse", she said, "but there are lots of things we can do to help each other get off and I'd really like to do them with you!"

"You like these, don't you Eddie?" she asked, glancing down at her bare bosom.

"Of course", I replied, "they are gorgeous."

"I could tellyou did", she exclaimed, "Because it looks like you have a tent pole holding up the front of your sweat pants!"

I blushed again and then laughed. Then I reached out and slid my hands under her breasts, cupping them and feeling the weight. I squeezed them and felt the nipples hard against my palms. Annie was smiling and let out a soft moan as my hands explored her.

And then she took charge, pushing me back into the chair and kneeling down in front of me. She rubbed my erection through my sweats and gave it a tight squeeze. A low groan escaped my lips as she touched me for that first time. She slid off my sweats and briefs and was soon stroking my bare cock.

"It's bigger than I thought Eddie" she whispered as her fingertips slid slowly up and down the rock hard shaft.

Annie's big breasts brushed my thighs as she stroked me. I was in heaven.

And then she leaned forward and kissed my swollen cockhead. I almost came right then and there. My mind was racing and I was totally in her control. Annie took the head of my cock into her mouth and sucked it gently as she continued to stroke me. Then she moved her lips away and looked up into my eyes and said, "You like that Eddie?"

I am sure I muttered something completely unintelligible at that point, but I nodded my head and she smiled that beautiful smile of hers before moving her lips back to my cock. Her lips slid up and down my cock and I was squirming and moaning in the chair, right on the edge of cumming.

"Ohhhh Annie," I moaned, "That feels so good!"

Her head bobbed up and down and soft sucking sounds filled the quiet of the room. I could tell she was into this and seemed to be enjoying it as much as I was.

My hips raised as my cock throbbed in her mouth. "I think I'm going to cum!" I exclaimed. She took me deep one last time and then slowly pulled her lips up and off my shaft. Her fingers encircled my cock and she began to stroke me again.

I could hold back no longer and with a loud cry of pleasure escaping my lips I came. Spurt after spurt of hot creamy cum shot from the tip of my cock and onto Annie's ample breasts. She giggled as my jizz coated her flesh, looking very satisfied at what she had accomplished.

She continued stroking until every drop of cum was drained from my loins. I had never in my life experienced anything like the pleasure Annie had just given me. I slumped back in the chair, my body limp. Annie just smiled at me and as I watched, lifted her breast to her lips and slowly licked one of the globs of cum into her mouth.

"Mmmmm," she whispered "You were delicious Eddie!"

Then, she stood up, stripped off the rest of her clothes and walked to the couch. Lying down and spreading her legs, she looked over at me and breathed, "My turn Eddie!"

How could I say no. I stood and kicked off the pants and briefs that were still around one ankle and slowly walked toward her, pulling my shirt off as I did. I stopped and let my eyes roam over the lush curves of her body. Over those the two globes of flesh that I had just christened with my cum; over the swell of her belly; over the curves of her hips; and down to her shapely legs. My eyes lingered at the dark tuft of hair between her legs that had just a little flash of pink showing. I knelt down and placed my hands on her legs, spreading them just a bit wider as my head dipped down towards her mound. My nostrils caught the musky scent of her as my tongue flicked out and I licked up and down the slit. As I did, Annie spread the lips for me with her fingertips. Her pussy tasted good and it was so very hot and wet.

I licked all around the velvet flesh and her quivers told me when I found a sensitive spot. I rolled my tongue around the little button of extended flesh and she began to whimper.

Her fingers gripped my hair and she guided my exploration of her beautiful pussy. She guided me down so that I could push my tongue inside. I started to fuck her with my tongue, pushing it in, trying to get as deep as I could. She was moaning and calling my name and her bottom rose from the couch.

She guided my lips back to her clit and whispered, "Finger me Eddie!"

I was happy to oblige and began moving my finger in and out of her tight pussy as I started to gently suckle that pulsing button of flesh. She began squirming and her breath was now coming in pants. I could hear her cries getting louder and knew she was close to cumming.

I pushed a second finger into her and with that she lost control, gripping me, pulling my mouth tight to her and crying out in pleasure. My face was soaked with her juices that seemed to gush from her hot center. I kept rolling my tongue against her clit until she pulled me away, saying, "Enough, Eddie, enough!"

I looked up at her and smiled. I could see the satisfied look on her face and knew that her pleasure had equalled mine. I moved around and kissed her gently on the lips, then wrapped my arms around her and hugged her tight.

It had happened so unexpectedly and both of us were momentarily at a loss for words. After a bit Annie got up, picked up her clothes and moved towards the bathroom. I grinned as I watched the sway of her round ass as she moved away. I dressed and when she came back to the room, she was dressed as well. We talked then, discussing how we felt about what had just happened and how it might affect our friendship. We decided that we both wanted the sex to continue and we worked out some ground rules about being what Annie called "suck buddies". We ended the night pleasuring each other a second time, Annie giving me another blowjob, but this time letting me cum in her mouth. I, in turn went down on her again, this time continuing as she experienced multiple orgasms.

We continued this "friends pleasing each other" relationship throughout the rest of the school year. We got to know each other's bodies and what things to do to give the most pleasure. As the school year was coming to an end, we realized that our relationship was nearing a crossroads as well. I was heading north for the summer to work in a mining camp and Annie was off to England to stay with relatives and explore the country.

As we were packing up our stuff to head away for the summer, Annie dropped a bombshell, not only was she going to England for the summer, but she had applied and gotten into a prestigious university over there and would not be coming back in the fall.

I tried not to show my disappointment when she told me, but I was devastated. Being naive, I had just assumed we would be back together the next year, sharing the suite and continuing to enjoy one another. Besides the sex, Annie was my best friend and confidant and I knew I was truly going to miss her.

Our last night before leaving, I took her out for a good bye dinner at our favourite little neighbourhood restaurant. We spent the night reminiscing about the past year and our many years of friendship. We vowed to keep in touch and we both hoped that one day we would be together again.

We walked back to the suite hand in hand, not saying a word. When we got home, we gave each other a soft kiss and then headed to our rooms to bed. I undressed and lay in my bed, eyes wide open and staring at the ceiling, wanting to go to Annie one last time, but not knowing if I should.

Then, the door opened and Annie entered the room. I saw she was naked and watched her in the dim light as she moved into the room and stood by the bed, just looking at me. "Are you awake?" she whispered.

"Yes", I replied.

"Eddie," she breathed, "I have been thinking about this for awhile, and I want you to make love to me. All the way, not just like we have been doing. I want you to be my first, no one else!"

I reached out my hand and took hers and squeezed it.

"I brought this," she said, handing me a condom, "I was hoping you would say yes."

And then we made love for the first time. It was sweet and unrushed. We kissed, we caressed, and we touched. It was as if we had never been together before. Slowly we pleasured one another until our bodies were ready to come together completely.

Annie slid the condom onto my throbbing shaft and then pulled me to her. She gasped as I entered her for the first time. I took it slow, savouring the new sensations and enjoying the intimacy of this special moment. I kissed Annie and looked into her eyes. I saw a single tear trickle down her cheek as she smiled that beautiful smile of hers at me. As the sweet sensations rose our bodies moved in rhythm towards the heights of passion. Soft moans came from our lips as together we passed the point of no return and our bodies shook with pleasure. Afterwards, I held her tight, showering her face with soft kisses. It was an incredible gift she had given me and I was glad that Annie was my first. We said nothing, for there was nothing to be said and after a time fell asleep in one another's arms.

We both knew that we were going our separate ways, but that there would forever be a bond between us...