During Christmas and the next few days I was floating on cloud nine, I was even overly nice to my younger brother Chris offering to take him and his friends shopping at one of the malls. My mom was concerned, not sure what had gotten into me. She finally asked if there was a "girl" behind my behavior change. "Sort of" was all I could reply, forcing her to drop the topic. I waited patiently for Mrs. Alexander, Olivia, to call, hoping, praying there would be another babysitting opportunity. I waited and waited, what seems like years, though it was only four days until I received the call. It was Olivia asking if I could baby sit Melissa New Years Eve. She apologized again for the last minute request. Apparently they were going out of town for the day, spending a night at some bigwig's place in the mountains and Katie could only stay during the day. She asked if I could spend the night at their place and that they would be back by noon on the First. I of course agreed, given I had no plans anyway. After a moment of silence, Olivia then suggested I come by the next day and she would give me special instructions. In saying it she laughed in her gleeful way which I interpreted in only one way – we were going to have sex again. She didn't make any overt comment about what happened between us or what might happen again, I just let it go.
Though the Alexanders lived only ten minutes away I left thirty minutes early, forcing me to drive around the neighborhood a bit. Eventually it was noon and I rang the doorbell, not a second late. I had no idea what to expect, if Melissa or even Mr. Alexander were around, or if it was just Olivia and I – she gave no indication of what was in store for me. She opened the door with her usual sense of glee and joy-with-the-world smile and gave me a small peck on the cheek as she welcomed me inside. I didn't say anything or do anything, not sure who was around.
Olivia sat me down on the sofa and then excused herself for a few minutes, heading up the stairs. I sat nervously in the quiet house, making me think that Mr. Alexander and Melissa were out for the day. I then heard Olivia call me, asking me to come upstairs. I jumped out of the couch, bouncing two steps at a time up the staircase to her bedroom door, which was open just ajar.
"Olivia?" I called from outside the door, my heart racing with anticipation.
"Come in, loverboy!"
I opened the door and there was Olivia, standing at the foot of the bed in a black teddy, nylons and stiletto heels – just as in several of the pictures in her photo album. I gasped, my jaw dropping, lost in her beauty, her raw sexuality.
"You are so gorgeous, so sexy. I am the luckiest guy. I can't believe..."
"Shhhhhh" she commanded, waving me over towards her.
I walked right up to her, grabbed her in my arms, and kissed her. My hands went roaming over her back, cupping her ass cheeks and pulling her into me tightly, my hard cock pressed against her.
"Hurry," she said, "we don't have much time, William took Melissa to one of her friend's in Englewood and they will be back soon. But we have enough time to take care of this!" she said, reaching down and cupping my crotch. She slithered down my body, rubbing her tits against my chest, and deftly undid my jeans, pulling them and my briefs down, freeing my hard cock.
She wasted no time licking and kissing my cock, up and down my shaft before placing it in her mouth. She began by just sucking the tip, driving me crazy, wanting to feel my cock fully in her mouth. I started humping my hips, then grabbed her head with both my hands and gently pushed my cock further into her mouth until I was completely buried. God, what a sensation it was, particularly given the view I had of her perfect little ass sticking out behind her.
She sucked me a few times, and given my youthfulness, it didn't take long until I was ready to cum. I wanted to cum in her mouth and held my hands tight on her head as my muscles tightened and I unleashed a load of cum. I heard her gagging a bit as she tried to swallow it all and released her. As she pulled her face away from my cock, another spurt let loose, hitting her on the chin. Olivia laughed with joy, scooping up the cum and placing it into her mouth.
She stood up again and leaned in to kiss me. I couldn't refuse her, but the sudden thought of tasting my cum on her lips didn't excite me. I kissed her, but reluctantly, she sensed my discomfort and pulled away.
"Trust me, it tastes great!" she said with a huge smile on her face. "It's normal to taste yourself, don't be afraid, it turns a woman on to have a man comfortable enough to kiss her after filling her mouth with his cum."
I needed no more encouragement and initiated a kiss with her, opening my mouth to allow my tongue to explore hers and taste my own cum mixed with her saliva. It was a new experience for me; everything I did with Olivia was a new experience. With her, I was a different person, she gave me confidence.
"God, how I want that beautiful cock of yours inside of me, pumping into my wet pussy," she sensually whispered as she rubbed her hand over it. "But we can't, there's no time, you need to go now. Please hurry!"
"But, but ..."
"Shhhhh, hurry, I know, we will have time soon, trust me."
She watched me pull up my jeans then sauntered over and kissed me passionately. I couldn't let go of her, I didn't ever want to let go of her, but she slowly backed me up towards the door, finally breaking the kiss as she shooed me down the stairs. I let myself out and drove not really sure where I was heading; I couldn't go home but didn't have any other place to go. I drove out a ways and as it turned out, I was passing Cinderella City mall and decided a walk through the mall might distract me sufficiently.
I wandered aimlessly not really paying much attention until I heard my name called out. I stopped, turning around, wondering who would notice me to begin with and then have the interest in meeting me. As I turned around I saw, of all people, Katie, along with two other girls from our class, Meagan and Beth, who were whispering to Katie. I could easily guess they were asking her why she bothered to call out my name, now they would have to chat with the loser.
I decided to ignore them as best I could and focused instead on my new found confidence, on Olivia's words and guidance of stepping up to bat. Without flinching I greeted Katie back and said a cursory hi to Meagan and Beth. I asked how their Christmas was and joked if they were already returning the gifts from their grandparents or something. They all laughed, as that was exactly what they were doing. I also noticed that Meagan and Beth were looking at each other with big question marks on their faces, as if they were asking one another, who is this guy. Katie seemed to take joy in my ability to talk.
Katie then asked if Olivia spoke to me about the 31st night and I assured her that it was no problem. She apologized and thanked me profusely for my willingness to take over. On parting, Katie said she would see me in a few days.
Though I would not have the opportunity of meeting Olivia, the idea of seeing Katie at the Alexanders' began to excite me. Since moving to Denver three years earlier I had had a crush on Katie. She was the perfect girl-next-door type, naturally beautiful with short cropped curly dirty-blonde hair, tall and slender body, radiant eyes, and small, pert breasts. She also had an amazing ass and firm, long legs. She seemed to always smile and was very intelligent, one of the smarter girls in our class.
Late in the spring of the previous year, our Junior year, she changed. Her eyes had become distant and cold, she rarely smiled, and never spoke up in class. I noticed the transformation, but of course never broached the subject with her; in fact, I never really spoke with her at all, or anyone for that matter.
Over the summer months I didn't think about it much and when our Senior year commenced, Katie was back to her usual, smiling self. Only, there was another change in her – she actually approached me several times and spoke to me. My loner status didn't seem to bother her and she seemed less concerned about how others were going to judge her. Of course, each time she approached me I usually fumbled through the conversation, being so shy and having such little self-confidence.
Though Olivia had begun to instill in me confidence and gave me instructions on how to interact with women, it was still all so new. I felt comfortable when I had met Katie at the mall but now it was going to be just her and I, and of course little Melissa. The thought of being alone with her made me nervous, making me think about how I was going to come off as such a loser when we met, the though of which made me even more nervous.
It was too late to back out, I was committed to watch Melissa and spend the night of the 31st. When I drove up to the Alexanders' house I parked in the driveway and took several deep breaths before grabbing my bag and walking up to the door. Katie answered and welcomed me in; I was unable to say much more than "hi." Fortunately, Melissa jumped up and ran over to greet me, saving me from an awkward silence with Katie.
With Melissa present I was able to make some small talk with Katie, giving me time to find my place, remembering my times with Olivia. We talked about their day then Katie passed along the instructions for the night. I then quizzed her about the party she was attending tonight. She explained that every year Dillon's family went to the Country Club party and he asked her along. Dillon was the rich kid everybody loved. Smart, though not intelligent, fun loving, gracious, though certainly not that kind. He and Katie were the "perfect" couple, or so everybody said.
Then Katie started to quiz me on why I didn't have any plans for the night.
"You want the long version or the short version?" I replied, laughing, more to myself than anything.
She sat a moment in silence, just looking at me, like she was trying to see into me.
"The long version."
"But don't you have to get going to your country club party? I don't want to bore you and keep you from your fun."