Bed & Breafast

I.

My father died when I was 17. My biological mother was out of the picture, and the will stipulated that my legal guardian would be Vanessa, a friend of the family's living in a small town about twenty miles away from ours. I hardly knew her. My parents, actually, had few really close friends, and I had only seen Vanessa a few times in my life—and not recently at that. My plan was to bide my time and be as little trouble to her as possible until I turned eighteen and started college. I wasn't thrilled about moving away from my friends and imposing on a forty-five year-old woman I barely knew. I had probably missed the wrestling try-outs at my new school, so I would not even have that outlet to work off my grief and excess physical energy.

Vanessa seemed pleasant enough, from my vague recollection of her. I knew she had been a sorority sister of my mom's. She was the type who wore a lot of make-up and had a bit too much to drink at my parents' parties. When I was a little kid I hated it when my mom's friends would leave lipstick traces on my cheek. I would run to bathroom to wash them off as they laughed at me. I half remembered that Vanessa had been the ringleader in this harmless fun.

After packing up a few things I waited by the front door for her to pick me up. An attorney would take care of selling the house and other details. A distant uncle would be the trustee of my father's estate until I turned 21. As we drove to her house Vanessa talked about the bond she had had with my mother in college. She hoped she could help me through the next nine months or so before I graduated from high school, and even after that... I didn't have much to say but I had the presence of mind of thank her, at least, for taking me in. I told her that I would clean up after myself and not give her any trouble. She told me that she ran a bed and breakfast a block from her house, with her daughter Rita, and that they had plenty of room for me at her house.

II.

A few weeks later, after dinner, she called me in to her bedroom to have a talk. "Jason," she said, "I think we need to talk. I know you miss your father, but you need to come out of your shell. You seem to shrink away when I try to give you hugs and you barely have anything to say to me. You just come home and go straight to your room. Do you have any friends at school? If you want to see someone we can arrange that. I know it must be difficult time for you." I explained that I didn't really see the need for a therapist. I hadn't been close to my dad, a workaholic, though of course this made the loss even harder for me to bear. I didn't want to be an imposition on the lives of her or her daughter. Kids left me alone, but they weren't particularly welcoming either, since as a wrestler for a rival school I had put a guy from their team in the hospital. It wasn't intentional or personal; it was just the typical injury in my sport. I would be fine in any case, I tried to reassure her.

We were sitting on the edge of her bed and she put her arms around me. I had always been uncomfortable with physical contact with the opposite sex, but I let her hug me for a few minutes, so as not to be rude. "Let me help you," she said. I allowed her to keep her arms around me for a few minutes more without saying anything, but then excused myself.

I had been careful not to stain the sheets or my underwear with cum since I had moved in. That night, though, I awoke with a huge hard-on and jerked myself off while thinking of Vanessa and my mom's other friends smearing my cheeks with their lipstick. It was on oddly childish fantasy for a seventeen-year old boy, but the strain of living with her in alien surroundings was too much for me. She left her bras hanging to dry in the bathroom for me to see, and wasn't too careful about covering up her cleavage in the morning.

We agreed that I didn't need to see a therapist right away, but that we would talk for a few minutes every evening before bed. When I came into her room she would typically hold my hands or embrace me, as I became gradually more comfortable with her touch. She gently rubbed my shoulders and offered her unconditional support, kissing me on the cheek before allowing me to to back to my room. I would go to bed and fantasize about her giving me a blow job. I knew she had observed the stains on my sheets, but after a while I stopped caring.