I lived at my parents condo on a bay on lake Michigan during the summers when I was in college. When I was about 19, I worked the summer at a very upscale restaurant. I usually worked 4 or 5 pm until 10 or 11pm depending on what they needed on the weekdays and 5pm to close Saturday night with Monday, Friday and Sunday off. This was a great schedule because it afforded me the afternoon for sailing, water skiing and hanging out with my friends or whatever. Oh yeah and the drinking age was 18 at the time, so we did some drinking.
The Condo was part of building with 10 units and docks and mooring for boats in front. Additional, my parents were gone with my younger brothers for most of the summer boating around the Great Lakes. I love to sleep nude and my bedroom which was on the first floor. From the waterside of the condo there was a deck, then living room, then kitchenette, then hall with bathroom and then my bedroom in back. So if you were on the deck, you could see down the hall into my bedroom and see my bed. It was fun to be nude with the possibility of someone seeing in or see people pass as I moved from bathroom to bedroom or be on the bed.
The family in the condo next door was also active in boating and the father was gone during most of the weekdays. They had 3 kids with their oldest, Grace, 14 who was not only pretty, but a real handful. In fact she could be a real witch at times. What I did not understand well at the time was how puberty effect 14 year old girls. Had 3 brothers and no exposure to PMS and everything that went with it. Grace and I got a long well and always wanted to tag-a-long with me and many times I would let her come along if when it worked out.
Grace's mom, Mrs. P is what I called her, was slender athletic build, maybe 120 lbs and C cup, no waist, blue eyes, dark hair and could sport a bikini quite well. Even though I was 19 and worked late, I was an early riser and up usually by 8:30 or 9 am. She would invite me over often for coffee which I loved and some kind of baked goods that were to die for. Quite often I would shed my clothes take a short snooze before lunch, then grab something to eat and spend the afternoon out with friends and on the lake. And yeah, often that included masturbation while stretched out on the bed.
One weekend Grace's parents needed to be gone for the weekend and she want to go for a few days and she was absolutely adamant about not being part of it. Her friends her age were not up on vacation yet and no other family except an Uncle 45 miles inland. Grace was really putting up a fight and was an absolute witch to her siblings and parents.
When I got up one Wednesday morning, groggy from working late, pulled only some shorts on and wondered out to the deck when Mrs. P invited me over. She had caramel rolls today and I was in heaven with my coffee. I also could not keep my eyes off Mrs. P because of the July heat, she only had a bikini (the kind with ties in back) on sitting on a bench seat with her back exposed to the door to the condo. She shared with me how Gracie was obstinate this morning in a 'mood'. The family had to run home for the weekend and she did not want to go, claiming she was old enough to stay by herself. As she talking, Gracie appeared at the door and I interrupted Mrs. P by saying hi to Gracie. Mrs. P stopped talking about her and offered her rolls and juice.
Gracie continuing to object to the trip, but she had an extra sweet and I am a good girl smile on pleading her case in as much of a grown up manor that she could muster. Mrs. P response was a no, but she would discuss it with her dad before giving a final answer. Gracie, rolled her eyes and got up to go back in. As she passed her mom, she said, 'On mom your bikini straps are not tied very well, here let me help'. What she did then was to tie them into double knots and pulled them extra tight. I could not tell if Mrs. P knew what she did, but I didn't think to say anything.
Mrs. P and talked some more including my lack of sex life. It was easy to talk to her about how it was difficult for me to be alone with girls my age because I would get all nervous and I could not control my body. I told her So I was still very inexperienced about the female body and blushed once I realized who and what I said. Mrs. P made me blush even more when she asked if I was still a virgin. I sort of blurted out I have gotten to second base a few times, but that was it. Now feeling so uncomfortable, I excused myself to run some errands. About 11:30, I was back to the condo and threw some clothes in the clothes washer including the clothes I had on. Walking nude back to my room I flopped on the bed for a snooze and was out like a light. I loved these naps.
About noon, I heard Mrs. P calling my name at the door to the deck. It startled me so much so I jumped up, naked of course, and as is usual for 19 year old, sporting one hell of a woody. When I roll out of the bed I am standing right in the doorway to my room and it is a straight shot down the hallway to the sliding glass door where Mrs. P was standing. For what seemed forever, I stood there a moment like a deer in headlights and she smiled and clearly saw me at full attention. Because I cleaned the floor up of all my dirty clothes nothing in easy reach except a bath towel I used that morning. So I grabbed it and wrapped up with that and walked out. When I got to the living room where Mrs. P now was standing and smiling, I said, 'Hi, sorry I was taking a snooze. What's up'. I was obviously blushing and Mrs. P said, 'Sorry, I hope I was not interrupting anything fun, but I need a hand'. She continue to tell me how her daughter knotted her bikini top and her younger kids could get them undone and Gracie was out her walk.
With the towel wrapped around me I tried to undo the knots. They were very tight and after trying them both, I began to grow hard from the smell and touch of her skin. I asked her to come over to the kitchen area to get a better view give myself a minute to arrange my towel again. As she approached me, she look down and could see how my penis was making the towel stick out. She smiled at me then turned her back to me so I could try again. This time I used a fork tine to pull the tie that went around her neck. I finally got it lose and she then held it in place while I work on the lower on. After a few minutes of working on the lower strap, she wanted to see what I was dealing with so we went back to the bathroom so she in the mirror.
During this time we were chatting about my 'date' this afternoon and she was giving some tips. I invited a girl to go sailing and Mrs. P was really cool about it and thinking about what I should do. By now I had been working at the lower one for some time when she said, 'You know, so you are more relaxed and not worrying about your body you should masturbate before you go.' I just about stabbed myself with the fork. I looked at her in the mirror and she was smiling. It did not help that my penis was growing hard again and now at the point of throbbing.
At that point, as she turned around she said, 'here, let me give it a try.' With me standing with my mouth open and certainly blushing, she let go of the top straps so her top dropped revealing some beautiful breasts and pert nipples. She then pulled the top around her so the ties were in front of her then turned to face me. She asked for the fork, which I gave to her while I stared at her breasts. I penis was throbbing. She looked at me as I stared at her breasts and smiled. Then she said, 'I think you should masturbate now'. With that comment, she tugged on my towel enough to let it fall and my penis sprang lose. As I looked at her breast and she fiddled with her top I jacked off.
I was so close to Cumming in a few strokes and I turned toward the sink shot, but she stopped me and asked me to face her so she could watch. I exploded and my cum first hit her right between her breasts and then down. The second shot hit her about the navel and then down. The rest hit he legs and tummy and some on the floor. When I was done she used the towel to wipe up and then wrapped the cum stained towel around her under her arms to cover her breasts and left telling me she would wash the towel and return it.
The date went ok.