My girlfriend, Janet and I have lived together for about a year when her 18 year old daughter, Whitney was due to graduate from High school. Whitney was not sure what she was going to do following graduation and in an effort to get her and her mom closer, I offered to let her stay at our place for the summer. Janet and her ex split about 10 years ago and since Whitney didn’t want to move from her friends she stayed with her dad. Over the next several years, Janet and her daughter didn’t see much of each other and drifted apart. Janet went through some difficult years following the divorce and she was finally getting her life together when we met. She was very nervous as she didn’t know anything about Whitney and was scared that she would not like her because she abandoned her.
As I said, Janet struggled for many years but finally got her mind right and got a good job working for a plastic surgeon and treated herself to some modifications that definitely made her body look right. To be honest she was a knockout. She had huge perky breasts, thin waist line, dark skinned and neatly shave pussy and a very nice ass. Our sex life was crazy as well. I found out very quickly that Janet was what you would call a squirter. The first time this happened kind of freaked me out but after that I was extremely turned on by this. It made for some very messy bed sheets at times but what the hell it was worth it. Our favorite was in the bath and she would straddle my face while I licked her pussy and she would squirt all over my face. Anyway back to the story..
So the day arrived that Whitney was to move in. Everyone was very anxious and scared but excited at the same time. Whitney had the basement to herself and we gave her a lot of space the first week while she was adjusting to her new surroundings. Janet usually has to work every other Saturday so I would typically workout in the morning and go relax in our hot tub. We have the hot tub enclosed in the gazebo in our backyard. Due to the fact we are not used to company; I am always nude in the hot tub. This particular Saturday, I was getting a little overheated so I was sitting on the edge of the tub and as I often do, I started stroking my cock. I am not one to brag about my size; however Janet does enough of it for me. I am about 8 inches in length and fairly thick. Anyway, as I was strokng my cock, who should come barging in but Whitney.
She was clearly more scared than I was and she just stood there not knowing what to do. She than started crying and saying she should leave and how can she stay with us after seeing this and so on. I covered myself up and asked her to calm down and go ahead and get in the tub and I would as well so I wasn’t exposed. She reluctantly agreed to this and I am glad because let me tell you, Whitney in a bikini was incredible sight to look at. She definitely got her mom’s features and being 18 she had a very athletic body and her tits were incredible. My dick stayed hard even after all the uncomfortable discussions.
I apologized to her and explained that we just weren’t used to company and that I would make sure not to do that again. To my surprise she said that she understood and that she wasn’t mad but she just wasn’t sure what to say. She also said she didn’t want me to change any of my habits on her behalf. We sat there for about 15-20 minutes more just talking and getting to know each other when she asked if I would mind if she removed her top as she was getting too hot. Of course I wanted to scream YES! But I held back and told her to do what made her comfortable and I wouldn’t look. Of course this only lasted about 10 seconds and once I saw her incredible tits I couldn’t take my eyes off them. It also became somewhat clear to me that she was doing this on purpose and she was enjoying what was happening. She got out of the tub and sat on the edge and spread her legs looking directly at me and smiled. I was still sitting in the water with a raging hard on that was ready to explode at this point.
Her next words completely blew my mind. She asked me point blank what I was thinking about when I was jacking off before she walked in. She also said that she knew most guys jacked off but she had never seen one do it. I reluctantly told her that as was often the case I was fantasizing about her mother and some of the various sexual encounters we had been in over the previous year. Before I could tell her more, I told her that this had to stay between the two of us to which she eagerly agreed. I went on to tell her about the couple swinging parties her mother and I attended and to the threesomes we were part of. Her mother loved to lick other women’s pussies and likewise get hers licked while sucking my cock. I would often jack off watching her mother and another woman make love as that really turned hr mother on.
Whitney then asked if I would jack off for her so she could see what it was like. I was blown away by her request but so horny from the conversation and seeing her tits that I couldn’t say no. I climbed back up on the edge of the hot tub and started stroking my cock. Whitney moved back into the water and crossed over in front of me. She was an incredible site and just the look she had was making me so horny that I knew it wouldn’t take long to cum. I started moaning and screamed I’m cumming and she actually moved closer I started pumping out cum and the first spurt landed right on her chest and some hit her shoulder. I hadn’t ejaculated that much in a long time and she was just standing in front of me speechless. Of course immediately after I had done that I apologized and told her it was a mistake and we shouldn’t have done that. To my surprise she said she wasn’t sorry and hoped that she could see it again sometime. I made up an excuse about errands to run and got out the tub, got dressed and left the house for the rest of the day. My head was spinning as I didn’t know if she would tell her mother or what would happen.
The following day I approached Whitney and again said it was a mistake and we shouldn’t have done what we did. She agreed that we would not do it again and for the next month or so things went on fairly normal. During this time Whitney enrolled in a school of message therapy and we purchased her a massage table and some other equipment. She really seemed to enjoy the thought of this and I envisioned her being very good at it. Deep down i was excited at the thought of this beautiful girl giving me a message. She hinted at it a couple times but because she was new at it I think she was a bit scared to offer it up. About 2 months after our first encounter we again met at the hot tub on a Saturday morning. She had on her bikini and as promised I was wearing shorts. We did however start talking about sex and she stated it had been so long since she had been intimate with anyone and even confessed that she had only had sex one time and it was so quick she didn’t really enjoy it. I joked that I sure would love to show her how wonderful it was and she perked up and said she would love that. I told her I was joking and it seemed to really hurt her feelings. She kind of smiled and said that if she could get her mom to agree to it would I be up for it. I yelled HELL Ya! She then hinted that she had something in mind and for me not to jerk off in the hot tub as I may not need to and she quickly got up and left winking at me as she left.
Janet returned home later in the afternoon and Whitney asked her if she would like to have a shot at being her first message customer. Janet quickly agreed and they set a time for later that evening. We had set the table up in one of our spare rooms downstairs. Whitney had asked all of us if we could meet prior to the message and share a toast to her new venture. We agreed and proceeded to drink two bottles of wine doing so. Following that the two girls left me and went down to the message room. As they did, Whitney turned and winked at me and quietly said leave your cell phone on and be close to it.
As I paced across the floor, I could hear the soft music playing and got hard thinking of Whitney rubbing her hands all over her naked mom. About 15 minutes later, a text came across asking me to come down to the room and quietly come inside and sit on the chair that was placed next to the door. I damn near tripped trying to get down the stairs so fast. I did as instructed and when I entered the room, Janet was lying on the table completely nude with a small towel draped across her ass. Whitney put her finger on her lip indicating for me to be quiet. As I sat there my cock was straining against my shorts and I could tell Whitney loved it. At that point she was rubbing her legs and moving up close to her ass. Whitney asked mom if she was Ok and that if she was at any point uncomfortable to say so. I kept hearing low moans coming from Janet so I know she was enjoying the message. More to come from Whitney soon..