First Taste of Cum Part 371    
          by Bill Beaumonte (oral_guy_2000@yahoo.com)  



This work of fiction contains explicit material intended for adults over 18. If you are under 18 or are offended by non-traditional sex, do not continue.  




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Author’s note:
This series presents a number of independent stories of about youthful first blowjobs. Some of these are inspired by my readers. I hope you enjoy this series.


Sissy Sucker

    I 'm a guy in high school whose older brother has a neglectful girlfriend. He brother has a high sex drive and needs to cum multiple times a day, but his girlfriend only helps him cum a couple of times a month, contending that it should be enough for him. It's really been getting him down and I really felt for him.

"I wish there was something I could do to help," I said.

"Not unless you can suck me off," he said. That wasn't a reasonable way for me to help -- or so it seemed at first. We had this same conversation a couple of times, and each time I ended up wishing I could do that for him. I was straight and intended to stay that way, but I found myself wondering what it would be like to suck him.

I did a little online research and read some stories, and that just made me want to do it more. I decided to discuss it with my friend Rhiannon, a petite girl who was a close friend, but not a lover. We could talk about anything, but never were intimate. I would to have sex with her, but can't seem to find the words to broach the subject.

Rhiannon was thin, but with nice perky breasts and hips that were a little wider than you would expect for her size, but that always caught my attention. I fantasized about how hot her ass must look -- if only I got to see it.

Since I could trust Rhiannon completely, I decided to seek her advice. "My brother is stuck jacking-off because his girlfriend won't help him," I said to her one day, "I want to help him but I'm not sure."

"What aren't you sure about?" she asked.

"I could help him by sucking him," I said, "But I'm straight and want to stay that way."

"Well, do you want to suck him?" she asked.

"Kind of," I replied, "He's my brother and I want to help."

"So if you could suck him off and remain straight you would?" Rhiannon asked.

"Yes," I acknowledged.

"Now tell me the honest truth," she responded, "You really want to suck him, don't you?"

"I am curious about it, but my biggest hang-up is I want to stay straight," I said.

"If you were a girl you could suck him and still be straight," Rhiannon said.

"That's a fine insight," I said, "But do I look like a girl?"

"I could help you look like a girl," she stated.

"Wait a minute," I said, "You mean you think I should dress like a girl?"

"It's not what I think," she said, "It's how badly you want to suck your brother."

"I don't know about that," I said. I never thought about wearing girl's clothes before."

"We're best friends, right?" she asked. I nodded my head in agreement.

"Okay, I get it -- you want to suck your brother, but you're hung up on the straight issue. If you really want to suck him, I want to help you out -- what are friends for?"

I realized that my desire to suck my brother went beyond just being helpful to him. The more I thought about it the more I wanted his cock in my mouth. I thought Rhiannon figured that out. But I wasn't sure I could go as far as wearing girl's clothes.

"Rhiannon, I trust you," I said, "What do you think I should do?"

"My parents will be gone next Saturday," she said, "Why not come by and let me try to feminize you, and see if you like it?" Rhiannon was always a little kinky, so I decided to go along with her as see what happened.

The next day at school she handed me a paper bag and said, "Wear these the rest of the week and see how they work out." I opened the bag and saw that they were pink panties.

"I can't wear these!" I said.

"Sure you can -- they used to be my older brother's -- they should fit you just fine."

I thought about Reed, Rhiannon's older brother -- a panty boy? Well maybe the whole family was kinky!

When I got home I undressed and took the panties out of the bag. They were very soft. I rubbed them against my cock and was immediately aroused. I should tell you that my cock wasn't very big -- not like my brother's cock -- now he was a really manly guy. I was almost the opposite -- not very muscular, with shoulder-length hair and delicate features. I slipped the panties on and marveled at how nice they felt against my skin. I looked in a full length mirror and was amazed to see myself as a girl! I looked closely at my face and realized that with my hair and soft features I already nearly looked like a girl!

Kids at school had often picked on me, and I tried my best to act macho, but my body seemed to be working against me. I got dressed, keeping the panties on underneath. For the rest of the afternoon every time I walked around, I felt the soft fabric rubbing on my cock, balls and ass, arousing me as it did. Finally, I had to jack-off to relieve the tension!

On Saturday I went to Rhiannon's. The first thing she had me do was strip down to the panties, after which she looked me over very thoroughly. "Now show me how you walk like a girl," she said. I took a few steps and she stopped me. She instructed me to take each step toward the middle instead of straight ahead. It took a few attempts, but I finally got it right, and as I walked she said my ass shifted in a very sexy manner.

She began to fill the bathtub, and then told me to soak in there for a bit, and then she would shave me. The only body hair I had was very light, but she said I had to be completely smooth. She even began to shave my ass crack. When I asked why, she said, "I think you'll be arousing your brother so much he'll want more than a blowjob, and when he spreads your cheeks I want you to be completely inviting!"

I was embarrassed for Rhiannon to see my tiny boy cock, and she made it worse by commenting on it. It was especially humiliating to hear it from a girl!

"I'd always suspected," she said, "But now I know you are small there -- so this is probably just right for you." I wasn't entirely sure what she meant.

"You already have really nice feminine features," she said, "So we'll skip most of the makeup and just do lipstick." She had me watch in the mirror and instructed me as she applied the red lipstick.

"Now look in the mirror and smile," she directed. As I did, I saw a girl looking back.

"Your pretty, so you should pick a girl name," she said. I decided on Tina.

I was hard throughout Rhiannons work on me, which she clearly noticed.

"Now I need to check something," she said while taking hold of my hard little cock, "Now close your eyes and think about sucking your brother."

I closed my eyes and thought about my brothers manly cock entering my mouth. Rhiannon stroked me and my arousal increased. I imagined my brother approaching climax, and as I imagined him cumming in my mouth, that sent me over the edge and I came. Rhiannon continued stroking me until I was completely drained.

I opened my mouth and saw that Rhiannon captured my load in a small glass bowl. It looked bigger than my usual load, but her hand was a lot nicer than mine!

"Now how do you feel about sucking your brother?" she asked.

"Kind of ashamed," I confessed, "I wanted to until I came, but now I don't want to."

"I thought that might happen," she said, "You've had a 'change of heart' when you came, so we'll have to deal with that." She handed me the bowl of cum and said, "Drink this."

I held the bowl, looking at my load and had no intention of drinking it -- that was absolutely disgusting!

"This is no time to be timid," she said, "Now drink it -- and do it NOW!"

She may be just a wisp of a girl, but something in her commanding voice was irresistible, and I tipped the bowl and took my load into my mouth. The taste was terrible and it must have shown on my face.

"Don't swallow," she said. I had no intention of swallowing -- I wanted to spit it out immediately.

"Just hold it in your mouth until I tell you to swallow," she said. Somehow, I found myself obeying her outrageous demands.

It was difficult hold my cum in my mouth -- I feared I would puke if I couldn't spit it out soon!

Rhiannon brought a bra over and put it on me and put some rolled up socks in the cups to fill me out. I had to admit that I was starting to look pretty hot.

"Still feeling ashamed?" she asked. I shook my head "no". She told me to swallow, and I did, glad to be rid of the bad taste, only to end up with a strong aftertaste. I wondered if I'd really be able to suck off my brother -- but he was the reason I was going through all this!

"I think the bra and panties, along with lipstick is all you'll need to completely arouse your brother," she said, "And he'll cum better that way."

Rhiannon taught me how to put the bra on myself by putting it on backwards, hooking in the front, and then turning it around and slipping my arms under the straps. She had me do it three times to be sure I could do it right.

"There's just one thing left to do," she said, and held out a strange looking device, announcing, "It's a chastity cage, and will keep you in the mood to suck your brother."

I didn't understand, but watched in wonder as she put it on me, tucking me into the device and then snapping a brass lock shut. Then it hit me -- I couldn't jack off with that thing on me!

"Take it off," I insisted, "What if I lose the key -- then I'm screwed!"

"That won't happen," Rhiannon assured me, "I'll have the key and keep it safe."

"We don't have to do it this way," I insisted, "I won't jack-off until after sucking my brother."

"You won't have to worry about that," she said, "You won't cum until I unlock you."

"But I'll go crazy if I can't cum!" I said.

"Oh you'll cum," Rhiannon promised, "Every Sunday I'll unlock you and you can cum."

"But I'll be so horny all week!" I protested.

"Yes, you will be, and you'll suck really well because of it," she explained.

"Maybe this is the wrong thing to do," I said, "I'm not gay and shouldn't be doing this!"

"You're not gay, but not exactly," she said, "You are a sissy."

"A sissy?" I asked.

"Yes, as soon as I saw your small cock I knew for sure," Rhiannon confirmed, "Just like my brother Reed -- that was his chastity cage -- he wears a larger one now."

Before returning home, I wiped the lipstick off and got dressed, wearing the bra and panties under my boy clothes. And yes, the chastity cage underneath. As I departed, Rhiannon reminded me, "Take good care of your brother." She handed me the lipstick as I left.

I got home and went to see my brother. "Do you need to cum?" I asked.

"You wanna help?" he asked, and I nodded, asking him to come to my room in ten minutes.

I rushed to my room and took off my boy clothes and put on lipstick. I practiced walking like a girl, making sure my hips rolled.

There was a knock on the door and I opened it, showing my brother his cocksucker. The look on his face was priceless, and I turned and walked toward the bed, using my sexiest walk. Suddenly his hands were on me, turning me around and pressing his lips to mine, driving his tongue into my mouth. It could not resist, and I began to understand what it was to be a sissy.

My brother's hands were all over me, until he was ready for me to do what I'd planned. He unzipped and took out his cock. My time was now at hand, and I dropped to my knees, taking the huge cock into my mouth.

I'd fantasized about this, and even became a sissy to do this, and sucked eagerly. My tiny cock was straining in it's cage. But more important, I had a hard cock in my mouth and soon it filled my mouth with it's hot load. In my arousal it tasted really wonderful -- far better than my own load I swallowed earlier.

"You're my bitch!" said my brother as I swallowed, "Thanks, see you at bedtime."

My brother left and I put my boy clothes back on. I didn't need to wipe of my lipstick because it was all over my brother's cock.

From that point on, I blew my brother as often as he wanted -- usually three times a day. A couple of times he would have his friends over for a party and I blew all of them and loved every moment of it. I grew to appreciate my cage, because it kept me aroused and greatly improved my ability to suck.

My dear Rhiannon welcomed me every Sunday, when she would unlock and uncage me, then stroke me to orgasm. After being caged and sucking all week, I came strongly, shooting a huge load. Of course I swallowed every drop of my cum -- no longer feeling any guilt of shame -- I was happy to be a sissy cocksucker!

Special thanks to my online friend, Adam, for inspiring this story

  To be continued . . .

Feel free to contact me with your comments or requests.
    –Bill Beaumonte (oral_guy_2000@yahoo.com)