It was Friday and school was out for the weekend. When I got home I found a note from my mom. “Dad and I have gone to Grandmother. Please go to the Chipman’s who will explain all.” Here I am teen, well practically for I’ll be thirteen on my next birthday in a few months, and I’m treated like a little kid who can’t stay by himself. Of course, I did not have any choice since I don’t have my own key (again like a baby) so I went down the block to the neighbor’s house.
I knocked and when Mrs. Chipman answered she invited me in and even had a snack ready. I did my best to be really polite and asked what was happening. Beyond that Grandma was sick and my folks were not sure when they would return she had little information. I would probably being staying the night but we would have to wait until my parents called to know. As it was a super hot day she added “You may go swimming if you like, Timmy.”
The Chipman’s have a small above ground pool. “That would be great, Ma’am, but I have to go home for my swim suit.”
“No need to do that. Jami won’t be home for hours since she has team practice. My nephews, Ross and Felix, love skinny dipping when they are here and you probably will also.” Jami is her daughter, not quite a year younger but in my grade at school. Her nephews are fourteen and twelve respectively. I went to the guest room where I saw that Mom had left clothes and stuff for me to stay over. There I stripped down, wrapped the towel about me and went to cool off. The water was great and I had it all to myself.
I was enjoying the cool water when without warning there was a great splash. It was Jami. She had done a cannonball to startle me and as a greeting. She explained that her tennis team practice had been cancelled because of the heat. I immediately had fantasies that she was nude like I was but I quickly saw she was in a bathing suit as she jumped about. It really showed off her quickly growing boobs (well, they would be that soon if she grew like her mother had).© YLeeCoyote
I was still trying figure out how to handle my nudity when she dealt with it. “Don’t worry about being naked, Timmy. I know all about what boys have for I’ve been seeing my cousins naked for years. Felix even has pubes like his big brother Ross already.” That did not make me feel any better because he was younger especially as I was still unhappily bald except for a handful of hairs so she will see me as a little kid. Since she swam some I resumed doing so myself while worrying about getting out of the water. She even got me to play catch.
When Mrs. Chipman came to the pool there was not any way I could put it off any longer but she refused my towel request “Not until you rinse off. And Jami has been seeing her cousins for years so you’re not anything new.” I tried to cover my junk but I was not very successful during the rinse off with the garden hose and they both got good looks. It was terribly embarrassing. But it was to get worse, very much worse very quickly.
Back in the kitchen, I got the news. Granny was in the hospital and the folks were not sure when they would be back so you know where I was going to stay for a couple of days. Then there was the matter of that nastygram from school in my pack. The school had called midday and so my mom had arranged for Mrs. Chipman to sign it after she spanked me for my bad behavior. This was so I would not have to wait until they returned.
Mrs. Chipman lectured me a bit and then repositioned a chair into the spanking position. I was shocked. Out here rather than in the guest room? And with Jami here! I objected. That was shot down faster than a praying mantis grabs a fly.
She had me stand by her and yanked the towel from my waist leaving me fully naked again. It was a very short time before being yanked over her lap so my junk was not on display to the two females any longer. She started with a few hand spanks and increased my shame by giving Jami a spanking lesson. She hit hard with her hand but it got many times worse when she switched to the hairbrush. That small, but heavy hardwood abomination was really a paddle in disguise which really hurt. Its contact with my flesh was more concentrated than that of the big paddle in school and on the bare rather than my jeans. It did not help that I was OTK like a little kid who is expected to cry as he is spanked.
I almost managed not to cry when she handed the wicked hairbrush to Jami saying “Try a few spanks on the naughty boy, dear.” You would think that a tween girl would not hit as hard as an adult woman but you would be terribly wrong in this case. Jami was on the tennis team and was known for the awesome power of her swing. Regrettably, I can attest that it a was well-deserved reputation for the ten WHACKS she inflicted on me were far worse than her mother’s. I quickly descended into the mind space of a little boy being spanked and responded with sobs and then bawling before she stopped.
I was a mess as Jami lead me to the corner and parked me there with “Put your hands on your head, boy.” order. That my junk was totally on display was not in my conscious mind for the fire that was raging in my ass was all consuming. It was many times worse because a girl younger than I had a major role in enhancing the inferno.
After Mr. Chipman returned we had dinner but I did not enjoy it having to sit on my raw tail and even forced to remain naked much to Jami’s delight. I was informed that this was the normal procedure used for Jami’s cousins and she had been watching for many years. Eventually it was bedtime and in the morning I got dressed.
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My day did not get off to a good start when Jami told me how much she had enjoyed watching and even helping with my spanking. She positively beamed when she said “I’ll bet Nicole (her BFF) will turn green when I tell her about spanking you.” That made me turn me turn red and to even beg her not to tell and insisting that spankings are really private affairs. “We can talk about this later, little one.” she said with a chuckle and a very evil grin.
The morning was like a roller coaster ride. Shortly after breakfast Ross and Felix were dropped off for the day. That meant that I would have guys to play with but it got better as I learnt that the plan was for Mr. Chipman to take them to the ball game in the city. I was invited to join. Then the crash for Mr. Chipman suddenly got called to work and that plan was cancelled so that little pool was going to be crowded. It was a nice plan B, however.
Just as I was told, Ross and Felix did not give a thought to getting naked to get into the pool with both Jami and their aunt around. I asked them about this and they insisted that it was normal for their father and uncle grew up that way. Jami soon joined us in the refreshing water, of course, wearing her swim suit. We broke for lunch, Mrs. Chipman told us that she was going out for a few hours as planned. “I trust that I can leave you all alone for a while without violence.” They all agreed that was the case. I was prompted and also agreed.
I assumed, just as you probably did, that Ross – the oldest – would be in charge. That turned out to be wrong. No, it was not Felix either. Over the years the two brothers could consistently agree on only one thing – that they could not abide the other being in charge so that responsibility fell to Jami in these situations. She, OTOH, absolutely relished the post. The guys (especially Ross) did not like that Jami was younger but better than the alternatives and it worked.
“I’m sorta like a babysitter who’s in charge but, of course, my cousins don’t need a sitter anymore.” Jami explained cheerfully. “Sometimes, however, they get out of hand so I confiscate the game controller (or whatever is the cause) and use the hairbrush like I did yesterday. That quickly restores order and keeps the parents away.” We guys all blushed now that the fact that she roasted all of our butts was shared. It really was not bad since we were all in the same situation so it passed quickly.
We were taking a break resting on the back lawn when Ross and I got into a stupid argument. He thought that he was better than I because he had a full bush. We argued and it quickly got physical. Both Jami and Felix separated us. It was not a surprise that she immediately decreed that we were both to be spanked.
“Yes, Ma’am.” said Ross accepting his fate nonchalantly. Felix had to prod me to do the same. The warning that they would hold me down was a big convincer.
It was very hard to get over her lap as she sat on the porch steps with that horrid hairbrush in her hand. To be honest, I wanted to flee but I didn’t. This was definitely moving her up a notch in authority (like a sitter) for the day before she had only whacked me when I was over her mother’s lap.
Not only was it hard but it was also horrid getting over my classmate’s lap like a little boy to be spanked by his babysitter while naked. It was worse that she was only in a bathing suit so it was skin on skin. I quickly got a stiffy and wondered if she could feel it on her thigh. She started with her hand driven by her strong tennis arm. I don’t think that she held back for it hurt terribly. Felix even lectured me about behaving properly as she throughly spanked naked me with her cousins watching.
That hairbrush had slipped my mind but suddenly that was all I knew for she had driven it directly onto my tail. The nova was instantaneous. I howled. I yelped. She WHACKED HARD! She WHACKED HARD over and over. My resolve not to cry fled and I cried. I even bawled. Eventually she stopped and I just cried like a little kid. I was truly chastised. Embarrassingly everyone saw that I was still hard when I got up.
As I cried, it was time that Ross got his butt roasted. He surprised me by dashing up the steps to his clothes on the porch and pulling his belt from his jeans. He handed it to Jami and then bent over leaning on the steps with his butt stuck out. Jami handed the belt to Ross and ordered “Give him a dozen hard ones.” It certainly was a less humiliating position that I had just been in. I wish I had known earlier it was an option but it was too late now.
“Yes, ma’am.” he replied and started in. The sound when the belt landed was awesome indicating that he was not holding back. I’m sure that he liked thrashing his big brother who had to take it. I can’t be sure but it probably hurt more than the hairbrush but Ross took it silently and with dignity unlike my babyish show. Our original disagreement was over shadowed by this. Effectively I lost.
* * * * * * * * * *
Time passed as always and after breakfast on Sunday Mrs. Chipman said “Homework time, kids.” so that is what we did until a swim break and lunch. My ‘rents called and they were going to stay with Granny another night so I had to go get clothes for school. Mrs. Chipman had the key and Jami went with me. It was in my bedroom when she brought up the subject of keeping secrets. It only took her a few words to express the condition. “You are just a little boy and I am in charge of you. You shall obey me and get spanked when I decide that you need to be and nobody else needs to know.”
My puzzled looks got her to explain it would be like yesterday and she would be like a sitter. I knew that school would be impossible if the guys knew that she spanked me so I was trapped into agreeing.
“You have disturbed class several times which is quite naughty. I will spank you for that now. Stand still as I undress you.” And that is exactly what happened. I don’t really understand why but I could not resist her so I just stood like a dummy as she undressed me. It all felt weird. Weird even considering that I had been naked with her seeing me a lot over the last two days and then even this morning. Once I was naked she pulled me over her lap. My tail started to get warm very quickly when spanked me with her hand. She kept saying that I was her obedient hairless little boy. I began to agree with that. It felt so good when she comforted me afterwards. Then I dressed and we returned to her house.
By the time I was in bed that night I did not know what to think but I kept hearing her voice telling me the conditions over and over. After school on Monday I returned home and Mom was there. She knew that Jami had assisted Mrs. Chipman spanking me and approved. “It sounds like Jami could spank you properly all by herself. She would probably make a fine sitter for you.” mussed my mom. I agreed too quickly for I knew that it all was terribly true.