I'm indebted to NAMB (Not a Modest Boy) for permission to write a sequel to his story Dating Brenda which first appeared on Nialos Leaning's (now Puericil) site at https://puericil.netlify.app/fna/Namb/DB_Dating_Brenda.html and is now also on his own site at https://www.asstr.org/~NAMB/Shorts/Dating Brenda.htm. You should of course read his story first as it defines this universe and characters. I have endeavored to continue the theme of both the story and Nialos' site which holds that boys should not be modest and under the control of girls.
The following story is fiction about youth who is infatuated with a girl tries to please her in every way and fails. The story contains scenes of spanking, strapping, shaving, femdom and gay sex. If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.
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I was one very confused lad as I made my way home. I had a great time with Brenda at the pool all day even with her kid sister, Tracy, around. Never before had I been hard so much of the day as I had been this day. I knew what I would be doing later when I got to bed and was alone in the dark with my parents far away watching TV. I figured that I would get off at least three times before I dropped of into dreamland remembering how she smelt and felt as I put the sun block on her wonderful body. And, of course, that she touched me with her lips, hand and other parts of her beautiful body. That part was simple.
The other side of my brain was spinning because of all the rules (many still not stated) that I had to follow to be permitted to date her again. Of course, I had never heard any of the other boys tell of how their date's parents had such strict rules and especially never about the way they meted out discipline. I was very confused because I had to drop my pants and jerk off in front of her entire family – her Mother, her aunt and even her little sister – while Brenda (albeit gently) spanked me. It was terribly embarrassing yet at the same time extremely exciting sexually. It seemed very strange but Brenda and Tracy had both seen my entire body for what was covered by my bathing suit at the pool was very exposed back at her house before the four females. In fact, those four were the only people who had seen me cum beside my best friend when we jerked off together. I could not help to contrast this with that I had only seen the parts of her body which were basically the same as mine (although with different curves).
It was very thrilling that they each kissed me but especially when Brenda did. Well, it was just a simple kiss on my cheek but she also used her hand on my neither cheeks while I was jerking off. Of course, her spanks were not hard like when I got spanked at home by Mom (with her wooden spoon) but still it had added an extra thrill as I was demonstrating that I was a man.
When I got home, Mom did her usual interrogation bit and I told her that it had been a great day. She suggested that I call after dinner to thank Brenda for the date. I figured that Mom was right about such girl stuff so I did. Her Aunt Pat answered the phone and I was very polite and explaining why I was calling. She seemed pleasantly surprised and even asked if I had thought about the rules. "Yes, Aunt Pat, I want to follow them so I may continue to see Brenda."
"Thank you for the wonderful day, Brenda." I said as soon as I she got the phone. Aunt Pat did not tell her why I was calling and she was also surprised and pleased. "You understand that the next time you're naughty and I have spank you, I'll use more than just my hand." she asked.© YLeeCoyote
"Yes, Ma'am, I understand." I don't know why I called her "ma'am" but she sounded so authoritative, like the teachers at school, that I must have done it automatically.
This must have pleased her. "That's the right attitude, Russ. The weather forecast for Thursday is that it will be a scorcher. Would you like to take me to the pool again?"
Of course, I jumped at the chance. I even thanked Mom for suggesting that I call and that surprised her.
I said that I was tired and wanted to get to bed early which was only partly a lie. You already know why.
* * * * * * * * * *
For the next forty hours all I could think about was my upcoming second date with Brenda. Much of it was like the first once we got to the pool. I had invested in a swimmer's jockstrap to help hide my hard-on during the day. I know that it helped because while we were eating at the picnic table Brenda said that I was better behaved than the other day. I thanked her for that but then she asked how come. I was afraid to lie to her and yet it almost felt like cheating. "I'm wearing a joc…, er, an athletic supporter, Brenda."
She smiled at me and under the table she put her hand on my crotch and felt me. "Russ, that was a good thing to do. Even though you're very hard, it does not show which is nice and polite." I got even harder and shivers ran up and down my spine with her touch. She went on to ask me about calling her "ma'am" and I could not really explain why I had. "I like that you did, boy, for it shows that you respect for me. It would be good if you called me that whenever I tell you to do something. Understand?"
"Yes, Ma'am." I said. She smiled and gave me a quick peck on my cheek and rubbed me through the jock strap. After waiting a while before going back into the water, we went to pee and she told me that I must not play with myself but just pee. Again, I said "Yes, Ma'am." and was rewarded with a big smile.
Later in the pool she got close to me and was teasing me a lot. It got me extra excited and, most shamefully, I came in the pool. "Russ, that was very naughty and disrespectful." she said angrily.
I was so remorseful that I was practically in tears. "I'm sorry, Ma'am. You are so exciting that I lost control. Please punish me when we get home, Ma'am. I'm terribly sorry and ashamed." I did not understand what was happening but I did not want to be rejected by Brenda or her family. We talked a lot and I answered Brenda's every question fully and truthfully believing that she would know if I lied even in the slightest and there would be terrible consequences. She was very interested that I had jerked off so much thinking about her.
When we got back to her house, she told me to strip and stand in the corner with my hands on my head until she was ready to punish me. A week earlier I would have been very surprised to be told to undress by a girl but since I had already been naked in front of her and her family already it was not a shock now. It seemed like a very long time that I had to wait and I hoped that Brenda really believed that I was truly sorry.
When she came back and called me from the corner I saw that she had moved a simple chair to the middle of the room and was sitting in it. She gave me a long lecture about having to develop self-control but also praised my attitude of obedience to her. I got over her lap immediately when she ordered me to wanting to show complete obedience and respect. It felt very strange being over a lap for a spanking since I only had to bend over for my mother since I was eleven-years-old. It also made me feel very little – like a little boy especially since I was naked and she was fully dressed. I hoped it would not hurt very much like the first time when I was jerking off with them all watching.
That hurt enough that I yelped because it was not her hand. Later, I would see that she had used a flip-flop which was effectively a little rubber paddle. The spanking when on and on and my butt was hurting a lot. I was even, to my shame, sobbing a bit from a spanking from a girl. I knew that I did not want this to happen again even before Brenda stopped spanking me. I stood up as she ordered. I was surprised that my cock was super hard even though my butt was on fire. Brenda stood up next to me and took my hard rod in her hand and started to jerk me off. She could tell when I was getting close and stopped telling me that I may not cum until she told me to. After a few times I was begging her to let me cum and after a few more times she allowed me to. It was fantastic. If she hadn't used a towel to catch my spooge, I certainly would have blasted it all the way across the room.
I was thanking Brenda for all her kindnesses when Aunt Pat came in. I wanted to cover up but Brenda did not allow me and Aunt Pat even told me it was unnecessary. Brenda had the right to decide what I wore in her house and that would usually be just my birthday suit. "Remember, we have all seen you naked and even shooting off. You don't have to have any false modesty here, boy."
Tracy and her Mom came in then. Mrs. Fallon wanted to know how the day went and if I was a good boy. Brenda explained that I had been good mostly but still she had spanked me and I had to show my hot red tail to her Mom. Tracy insisted on a close inspection and even checked out my boy parts as she called them in addition to my red butt. She was disappointed that she missed both the spanking and my coming. (Frankly, I was glad but I was smart enough not to say so.)
I stayed there another half hour and found that I got more comfortable being naked. Brenda told me that she did not want me to jerk off again until she told me that I may and she would call me at eight in the morning to ask. It was very difficult not to jerk off and I even wore the jock strap with a cup to bed to help keep me from touching myself. Brenda was all I could think of and eventually I fell asleep. I was awoken by Brenda's call and happily I could tell her I had been a good boy and I had managed NOT to jerk off. Brenda was a real angel and told me to remove the protection and gave me permission to jerk off. I had to stop and pause five times before she allowed me to cum. It was a most fantastic cum though. I thanked her profusely.
* * * * * * * * * *
It has been almost a month since my first date with Brenda and I'm now very comfortable being naked in her house as she insist that I must be. I've even got to accept Tracy's constant interest in, as she puts it, my boy parts. Also, I've really gotten better at controlling my erections. This pleases Aunt Pat a lot and that is good because she in charge most of the time. Brenda, but especially Tracy, wanted to practice a needed babysitting skill – diapering a boy. I became their practice baby.
I was required to lie on a mat on the bed and Aunt Pat gave the first lesson. Although my heart is set on Brenda, it was Aunt Pat who showed how to powder and oil the baby to prevent diaper rash. Although she is an older woman (in college already) she is attractive and I got hard. I started to apologize for being rude but Aunt Pat said that was a normal reaction even of real baby boys. After that it did not take very long for her to get the corners together. She made sure that Brenda and Tracy understood how it had to be tight to prevent leaks even when plastic pants are also used. To test it, I expected that I would be required to pee but Aunt Pat said not this time and used an enema bag with warm water. She just stuck the tube down the front of the diaper and let the water flow.
Now it was time to do the less pleasant part – removing the wet diaper and cleaning the baby for a new one. Unfortunately, the powder and oil had made a mess of my little bush. Aunt Pat was unhappy at this as the girls tried to clean me off. Even doing it in the shower was a problem. Tracy suddenly yelled: "I know what we need to do. Get back into position, Russ." She dashed off to get something. Even Brenda and Aunt Pat did not know what she was after. She was back in a minute with the terrible device. "Babies don't have hair so we just have to remove his with this." She pushed me flat and both Brenda and Aunt Pat held me down apparently knowing what was about to happen. She turned the device on and started to push it into my bush. It hurt but she also had grabbed my dick and I could not get away. I watched in horror as she moved the thing over my pubis and yanking out each and every one of my hairs. I tried to complain but Brenda told me to be a good boy and do I as I was told. In a few minutes I was bald as a baby. "OK, Aunt Pat, we can continue now." said Tracy cheerfully.
After that I was diapered , flooded and cleaned up several times until Aunt Pat was satisfied with the girls' technique. I made the same assumption that the girls did until Aunt Pat pointed out that there is a messier side to the diaper business. (How could I have forgot about that!?) "We are going to have to get a bit messy by having Russ mess his diaper." I protested that I did not have to go, but that did not save me. Aunt Pat and Brenda held up my legs far apart and Tracy pushed a thing into my hole. "That will make you want to make number two, Russ. Now let the young ladies diaper you so you are ready."
She was absolutely right and a few minutes later I made a big stinky mess in my diaper. I was then order to pee to really make a bigger mess. They made me wait a while before cleaning me up. They did not like doing it but they got me very clean. Fortunately we only did that once.
Later, Brenda told me that she like me better without that messy hair above my pee-pee and that I look bigger without it. She also decided to reward me by jerking me off herself for being so helpful. Well, there are some compensations for losing one's pubes.
* * * * * * * * * *
Tracy also found a boyfriend but he was very different than I. I don't understand how or why but he did not have to obey Tracy like I had to obey Brenda. Kory and the others managed to have mutual respect and, secretly, I admired him. I heard Tracy say very nice things about him including that he was a man who knew how to respect a woman. The bad thing was that he looked down at me calling me henpecked, wuss, sissy and pussy and other things at various times. Brenda told me to ignore him for I was dating her – not him – and she liked me. Tracy always agreed with Kory and also talked down at me.
I'm sure it was those two that encouraged Branda to shave my pubis when the hair started to return. Kory even told me I did not deserve to have man-fur and told Brenda that she should keep me smooth.
The biggest disaster happened on rainy afternoon. I was at Brenda house and so were Tracy and Kory. We were alone because Brenda, her mother and aunt were delayed by a terrible storm which prevented them from driving home. Tracy and Kory had a secret conversation and then they came to me. I ended up confessing a lot about how much Brenda controlled my coming and then Kory said there was another way that was right for a sissy boy like me. Tracy started to order me about which was not that unusual and soon I was on my hands and knees on the floor. Tracy was next to me playing with my dick and then Kory was playing with my butt hole. They were making me feel very good and then before I knew what had happened, Kory had removed his fingers from my hole and replaced them with his hard cock. He had a very tight grip on my waist and with Tracy also holding me, I could not get free. Kory fucked me hard and something inside felt very good. I soon shot a large load and shortly after Kory yelled that he was coming and did. It was only then that I saw that the others had come in and saw what happened.
They had taken advantage of me and there was not any way it could be undone. Kory had fucked me that proved to him and Tracy that I was a sissy, pussy boy. Obviously, I liked it since I came first. Brenda, her Mother and Aunt did not seem to care that it had happened. Things did not change between Brenda and I.
* * * * * * * * * *
Actually, things did change between Brenda and I. We had been dating – going places together – three or four times a weeks and then I noticed that she was going with other boys rather than I. I guess that I should have realized things were over and stopped seeing her but I could not give her up. She also had more of her girl friends about and they, in the same way that Tracy did, were interested in my body. Since she kept me naked there was not any way to cover myself up. I knew that they were surprised that I did not have pubes as they mentioned it boasting that they had had them for a while and even their kid brothers did. I even more ashamed to say that they had been removed rather than being missing.
It was her slumber party that was the last straw. She had five friends over and she made me be a serving boy – a naked serving boy. There were all wearing robes over flimsy and reveling pj's while I was there. Brenda told me that I was to do something very special for her guests – just what I did after our very first date – jerk off. I just could not do it and things got worse. They jumped me and tied my hands behind my back and then had me lay over an ottoman. That left my butt sticking up, my tackle hanging where they could reach it. "Well, we are going to see you cum, boy. You're going to be sorry if you did not do as you are told. You will be punished for your disobedience." snarled Brenda. Her friends applauded.
The started my each playing with my cock and balls. I could not help but to get hard. They then spanked me with Brenda's Grandma's old wooden hairbrush. She showed it to me before it was used. That thing really packs a wallop and had me screaming very quickly although they kept playing with my rod to keep it hard. I could not imagine that it could get worse and hoped they would soon be satisfied when they made me come.
But, they had one more nasty to use. They kept playing with my bottom hole and getting their fingers into it. Brenda explained that boys have a special place inside that sort of like their own g-spots and the way to get to it is with a vibrator. A vibrator like this one she said showing it. There was not any way I could keep that out and some it was driving me crazy and she pushed it in and out rubbing my love-nut all the time. The girls commented on how I was leaking and then I exploded. They caught my stuff in a cup and was amazed at how much. As great as it was to cum like that I was wishing that the Earth would open and swallow me up.
That did not happen, but they untied me and sent me home. I was allowed to dress on the porch.
Back home I slipped in quietly and went right to bed. Brenda had even told me that since I had stopped following the rules, I was not permitted to date her again. I cried for hours knowing that Brenda did not care for me for she shamed and dumped me.
Things were even worse for at school every one knew and no one wanted to talk to me. All the time there were snickers directed at me. Actually, there was one person around who did not snub me and that was Kory. But he only wanted to see me in private so that he could use me as his pussy-boy. At least he was honest about it.
My life is now a total hell.
© Copyright A.I.L. June 6, 2010
The URL for this page is: https://yleecoyote.asslr.org/DatingBrenda2.html
Last updated: September 15, 2023