When I was a Kid 9

When I was a Kid... Chapter 9

By Redbuns

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Chapter 9

The waitress seemed a bit surprised when she returned with the cake and I was dressing. I think she was a bit disappointed by not seeing me still naked. I really couldn’t look at her, I was very embarrassed. It seems when getting my spanking in front of others, it becomes much more humiliating than if Maggie was disciplining me when we were alone in her basement.

The cake was decorated nicely with this writing: “Congratulations upon your entry into puberty.” That’s not exactly the kind of cake you’d want to share with your friends, but as I recall, it was very tasty! We spent some time on small talk, but I knew that something else would be happening once we got home, so I wasn’t very enthused. I was still standing because my butt was smarting from my most recent spanking. I also received an envelope from Maggie with a hand-made card congratulating me on “being able to squirt now” and something to the effect that she would be there for me, helping me, guiding me, and making sure I was headed in the right direction.

Mom reached down into her bag and pulled out a small gift wrapped package. She was all smiles as she handed it to me. It was light and felt flimsy, like it was a small t-shirt or something. I tore off the wrapping just as the waitress was coming in again with the check and to see if we’d like her to put the rest of the cake in a take-home box. I was puzzled as I unwrapped a white cloth with navy blue polka dots on it. Somehow, it looked vaguely familiar, but I just couldn’t place it. I looked up at mom who was beaming with a broad smile. “Alan, Maggie’s mother has concerns when your ejaculate splatters on her floors, and I don’t think we should use her cloths and rags to clean up the messes you produce, so I dug up one of your old cloth diapers! Seeing as you’ve now entered puberty, and since sometimes Maggie has you masturbating when you are visiting and when you are there for discipline, I just thought you would be a polite gentleman and have your own cloth to clean up your mess!” Maggie chimed in with: “We’ll call it your ‘boy towel’ instead of your old diaper.” The waitress started giggling as she witnessed this gift unwrapping and the ensuing dialogue! Dad had a nervous smile, I could tell he was uncomfortable but he didn’t say anything.

“Alan, you’re coming right over as soon as we get back; I can’t wait for you to try out your boy towel!” As if I couldn’t have been more embarrassed…the waitress was holding her sides laughing as mom handed her money to pay for the meal. Then Mom said to Maggie, “I’m sure I can find more of them so there will be an ample supply for you to have him use! When he soils them, send them back, and I’ll launder them and have Alan bring fresh ones over weekly.” While I thought Mrs. B was going a bit overboard when I had an orgasm on “her floors,” I thought her priorities were a bit misplaced. After all, it was her daughter, her 12 year old daughter who was the reason that I, the boy next door who would be 12 next month that caused those “messes” as she put it. To be honest, when I had an orgasm, it felt good, really good, but I also had this shameful feeling that I was messing things up. When Maggie had me “squirt” outdoors and had me point my penis toward the drain, I kind of felt a bit better, knowing that at least that time I wasn’t making so big a mess.

Mom continued with the gift giving as we were waiting for the waitress to bring the change back. I thought it was odd that Maggie would receive a gift; after all, it was supposed to be my party. But Mom handed Maggie a square package neatly wrapped in paper that one would use to give a gift to a little boy. When Maggie opened it, I couldn’t figure out what it was, but Maggie knew right away, but still gave mom a puzzling look…it was a few packs of Polaroid film. Maggie just looked up at mom with a questioning look on her face. “It’s for taking pictures of Alan when he’s had his spankings. I’d like to have a picture taken each week, have it dated, and placed in an album. I think it would be a great idea to document through the next few years, how well a job you do with Alan. It would also make a great memory book for him in the future.” At this time, the waitress came back in with the change, mom left a hefty tip for her. I was red faced as we got up to leave. The waitress thanked mom for the generous tip, and told her whenever she wanted to host another get-together like this one, just let them know, and she would make sure we could get this private room. When we walked through the restaurant, it seemed as if all eyes of the staff were on us, and I swear, every one of them was smiling or snickering at me as we walked out the door.

On the ride back home, Maggie gave me an option; I could get another spanking…OR let her bring me to orgasm, not once, but twice. Mom just smiled at me as I stuttered a bit, not sure which to choose. Maggie hadn’t really handled me that much, at least not where my penis was concerned. However, I’d already had a spanking that I was still feeling. I guess it was a no-brainer as I thought it over, then said; “I guess I’ll choose having two orgasms, but I need time in between them, I just can’t do it one right after the other.” To which Maggie smiled and patted my leg. “I expect you to go home, get out of your nice clothes, and head right over to my house and go down to your spanking room.” Then she asked if my mom would like to join us, to which mom just sighed and said, “Alan is getting to be a big boy now, he doesn’t need me to see this, after all, his erections are the reason I decided to have you take over his discipline. And now it’s all official, we have a signed and witnessed agreement where you get paid to do this!” I muttered under my breath something to the effect that I didn’t sign anything. Too bad Maggie heard that. She said, “Alan made a comment about not signing the agreement. I have an idea for him, why don’t I have Alan ‘sign’ the agreement by squirting his semen on the bottom of the page, under our signatures? What better way for him to put his mark on this document!” Mom laughed and nodded in assent. I really didn’t know what she was talking about, and then it hit me.

“You want me to masturbate on the paper?” I thought out loud! But it kind of did make sense, I guess I could do that. To which Maggie replied, “No, this time, I’m going to be the one who makes you squirt. We’ll get those papers “signed” by you before the night is done!” By this time, we’d turned into our driveway. Seeing as it was quite dark, I got out of the car and walked Maggie to her back door. She smiled at me and told me to hurry back. I turned, and quickly headed to my house.

Mom and dad had just gotten in the back door before me. “Alan, you’d better hurry and get undressed, I don’t want you to get anything on your new clothes.” I asked her “what do you think I should wear over to the Baron household?” She smiled and said, “It’s very dark outside, why don’t you just go over there in the nude? I think that would be the easiest!” She urged me to hurry and get over there as it was getting a bit late. I’d had quite a full day with shopping, swimming lessons, and the meal at the restaurant. I wasn’t sure I really wanted to have Maggie handle me to not one, but two orgasms, but the consequences for not being prompt were beginning to mull over in my mind. I quickly went to my room, took off my new clothes, shed my underwear, and wearing nothing but a forced smile, told my folks I’d be back as soon as it was over. Mom nodded, smiling at me, then turned to dad and told him to strip down, it was time for his spanking. Dad kind of smiled, shrugged his shoulders, and loosened his belt as I timidly went out the back door.

It felt strange walking out of my house naked. I mean, I’d done it in the daylight when I went to the Baron pool, but there was something mysterious and daring about going out in the darkness. I kind of scampered to their back door, and without knocking, I let myself in. Mrs. B greeted me as I entered, “Alan, thank your mother for me, the ‘boy towel’ is a real relief for me. Just make sure you clean up any of your messiness!” I blushed a little, realizing that down those stairs, I would be fondled to orgasm by Maggie. It was a bit thrilling, and a bit scary. I could feel my heart racing as I bounded down the stairway. The lights were already on in my spanking room, with no lights on in the laundry room where I usually changed. At first I thought this was odd, but then realized I had nothing to change out of!

Maggie was waiting for me. She’d changed from her nice dress into jeans and a t-shirt and wasn’t wearing any shoes. As soon as I saw her, my penis sprang to its throbbing fullness. She giggled, eyeing my erection. Since I wasn’t going to be spanked, there was no chair to set up. Instead, Maggie had placed the documents she and mom signed on the tiled floor, and had my boy towel over her shoulder. “Shall we get started? It looks as if you’re ready for the first one right now!” Then, grabbing me by my erection, she guided me to where the papers were on the floor. “Kneel down right here; I’m going to sit next to you.” Her tugging on my erection meant this first orgasm was going to happen very quickly, and I wanted to make sure I did it right.

Without letting go of my penis, Maggie plopped down on the floor next to me. She told me to look her in the eyes as she manipulated me. Even though she had her eyes on what she was doing, I stared into her face. At that moment, I realized I really had a liking for Maggie! She began to pump me, and in seconds, I loudly told her that I was about to come. Maggie used her other hand to move the documents where she thought I was going to squirt. I began groaning and shaking. The first blast went a little higher on the paper than she’d aimed, but the rest of my spasms were delivered right on target! My eyes never left her face, and I could see how excited she was, and the great big smile that graced her face as she continued to slowly pump my penis, shaking it to make sure she got the last of the drops on the bottom of the document. She wiped her hand on my boy towel and patted my bottom telling me what a good boy I was.

Maggie had me stand up and face her; she then took the boy towel and wiped the end of my now very sensitive penis of the oozing drops of semen that still seeped out. I was very sensitive, and kind of pulled away. She looked at me with a bit of anger in her face, but I explained about feeling extremely sensitive immediately after an orgasm. I told her it wasn’t like pain, but rather like having too much of a good thing. Something that would later on come to play!

I’d masturbated of course, and had once had an orgasm without using my hands when I was over her lap, but this was the first time someone other than me intentionally brought me to an orgasm, and I loved it! I loved having Maggie do this to me. I loved having someone else control the speed and grip on my penis as I approached the point of no return. I absolutely wanted this to happen again…and again…and again!

Maggie questioned me about my experience, about how I felt having her handle me, and what felt good, what wasn’t so good, and what she could do better the next time. I confided all to her, and she smiled deeply then tussled my hair and told me to get up.

Maggie asked me if I’d like to shoot some pool for a while until I was ready to do this again. At this point, I was willing to do most anything as long as I could have another release from her hand. She was a very good pool player, and I wasn’t so bad myself. We played a game of 8-ball, then she asked me if I was ready yet, but I suggest we play one more game. It was during that game that I began seriously thinking about what was going to happen to me in a few minutes, and bingo! My erection returned well before that second game was over.

When Maggie sunk the winning shot, she motioned me over to the side of the room where I usually had my discipline. This time, Maggie had me lie down on the floor. The tiles were a bit cold and shocked me for a moment. It wasn’t as if it was uncomfortable, just took a little getting used to. Then she sat cross legged next to me, leaned over, and began massaging my scrotum with one hand, and my penis with the other. As a boy, I was ready to come in nothing flat, and told her so. Once again, she told me to look only at her face, and as she pumped away, I could see a grin building as she could feel my body tense as my orgasm was imminent. This time I almost shouted at the top of my lungs, “I’m coming, oh please, here it comes!” and I began spurting. Though the volume wasn’t as large as the one I’d had earlier, it seemed to be just as intense. Once again, I watched as her face brightened with a big smile as she watched me squirt time and time again, making quite a mess all over my chest and belly, with my semen eventually filling my navel and spilling down my side. I was grunting and moaning at the top of my lungs which seemed to bring satisfaction from Maggie to no end.

When I was coming down from the orgasmic high, I noticed Mrs. Baron had come downstairs and was standing in the doorway with a big grin. “Make sure you clean up after yourself, Alan. I don’t want anyone to slip and fall on your mess!” With my heart racing, I slowly rose to a sitting position and reached for my old diaper, my “boy towel” as Maggie liked to call it. I wiped myself down, got on my hands and knees, and cleaned up the floor. I really didn’t realize just how much of a mess a boy can make until I had to clean everything up.

As I was on all fours, cleaning the floor, Maggie stood up and ran her hand through my hair, telling me I was a good boy, just like someone who had a dog would rub and pat their head when they’d fetched a shoe, or done a trick! Mrs. B asked Maggie if we’d like anything to eat, to which Maggie said, “I have some of the cake we had for dessert upstairs, I think Alan and I would like that and some milk. As soon as he’s done cleaning up the mess, we’ll head upstairs.” This was different from when I was spanked. Those Thursday evenings, we stayed downstairs and had cookies and milk, but this time I was going to be able to go upstairs!

When I’d finished cleaning up, Maggie checked the floor, patted my bare butt, and told me to take the soiled towel with me as we went up for a snack. Mrs. B was placing two glasses of milk on the table with two slices of cake for us. As we sat down, she joined us, and asked her husband to come into the kitchen.

As we began to eat cake and wash it down with milk, Maggie’s parents once again reiterated our agreement:

1.) It was fine for me to be naked in their pool as long as I didn’t have pubic hair – and that shaving it off was acceptable.

2.) It was acceptable for me to arrive at their house for any occasion naked, if that’s what Maggie wanted.

3.) While it was fine for Maggie to manipulate me and touch me, I was not to do the same to her without consent, in other words, no sex that Maggie didn’t initiate (this was new to me, and I sprang to a full erection again, fortunately, with everyone seated at the table, it went unnoticed at this time).

4.) I could not tell anyone about our arrangement without confiding with Maggie first, however, Maggie might do so without my consent if she felt it was necessary.

5.) I was encouraged to not hold back my emotions or my voice when I was being spanked and also when announcing my orgasm, and during my orgasm.

After some small talk, I looked at the clock and decided it was time to head on back home. I felt like I needed to take a shower, and I was exhausted. As we all got up from around the table, they all noticed my erection bobbing in front of me. They all smiled, even Mr. B as I picked up my boy towel and headed toward the door. “Why don’t you come on over for a day’s worth of swimming tomorrow; just head on over after you’ve had breakfast. It’s supposed to be sunny and hot. We need to work on your tan.” Those were the words from Maggie that hung in my mind as I walked home.

Entering my house, I was met by mom and dad. They asked me if I’d “signed” the agreement, to which I smiled and nodded my head. I just showed mom the extremely wet “boy towel” and she smiled with a knowing look. I then remembered that when I was leaving, mom told dad he was getting a spanking. Both mom and dad had satisfied smiles on their faces and I could only imagine what went on when I was getting off in the Baron basement!

After showering, I went to bed feeling drained and also satisfied. I guess that I was beginning to look at this arrangement in a more positive light. I have to say, I was looking forward to tomorrow and spending the entire day at the Baron pool.

(The End)