First Taste of Cum Part 259    
          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

    I'm Jeremy, a Junior High school guy with a unique experience. It all started when I got a new neighbor, Chris. He had long hair and looked a little feminine but seemed like a good guy. I went over and met him as he was moving in, and we quickly liked each other. It was summertime, with school not in session, so we had plenty of time to hang out together.

There weren't a lot of other kids nearby, so I saw Chris nearly every day. Chris lived with his father, who worked during the day, but there were certain times when Chris was mysteriously not available – he said he had "appointments", which peaked my curiosity.

I asked Chris about his appointments and he made light of them but would never give me any details, so I decided to nose around. I watched his house at his appointment time, but there was nothing to see. I persisted, and about a half hour later a car drove up and a man got out and went to the front door. A girl greeted him and let him in. That seemed really strange because I knew Chris was an only child. I watched and saw that the guy left about 20 minutes later.

I waited for the car to leave and then knocked on the door. It opened the girl said, "Oh shit!"

It sounded like Chris, so I asked, "Chris? Is that you?"

"Come in quickly," Chris said, and I entered.

"What's going on?" I asked, "I don't understand."

"I'm a sissy," Chris said.

"I don't get it," I replied.

"I like to dress up as a girl and pleasure men," Chris said.

"Pleasure them?" I queried, "How?"

"Usually blowjobs," Chris said, "But some like to fuck me. But you have to keep this secret!"

Now I understood – Chris was having sex with adult men – no wonder he was so secretive about it.

"I won't tell anyone," I promised, "But this is such a surprise – why do you do this?"

"My father got me started, but in time I grew to like it," Chris explained, "Now he has men make appointments to see me. He says men who like gurls like me will pay a lot for my services."

"So your own father is whoring you out?" I asked with surprise.

"Yes," Chris confessed, now looking ashamed, "But he puts half of what I earn into my college fund."

"And you like doing it?" I asked.

"I know it's hard to understand," Chris said, "But I really do. It all started when my father caught me wearing girl's panties and asked if I wanted to do what real girls do, and he taught me to blow him."

"It was difficult at first," Chris added, "But as I learned and got good at it, I really grew to like it."

"Would you like a blowjob?" Chris asked, "You're my friend, so you don't have to pay."

I'd never had a blowjob before but heard that they were a lot better than jacking-off, and quickly unzipped and Chris was kneeling before me, stoking me to erection. Soon Chris had me in his mouth and I was in heaven! No wonder men paid for this! It only took a few minutes until I shot my load into her mouth.

My knees felt weak, so I sat down on the couch, and Chris sat next to me. This had to be the very best way to cum, and I knew I wanted more – a lot more! I had never been close to a girl before and really found Chris to be attractive. I wasn't at all attracted to guys but was really drawn to Chris. I reached out and took Chris by the hand.

Chris responded by sliding closer to me. "That was really wonderful," I said, "But I'm feeling a little funny about it."

"You don’t have to return the favor," Chris said, “I was glad to suck you and don’t expect anything.”

"That's not what I mean," I said, "I'm not attracted to boys, but am kind of attracted to you. May I kiss you?"

"Let me brush my teeth first," Chris said, "You don't want to kiss me right after the blowjob."

I hadn't even thought of that – I just desired Chris, but it was really considerate to brush for me.

Chris returned and sat close to me, and our lips met. I'd never kissed a girl before, but this was magical!

I put my arms around Chris and our lips parted. I tasted his toothpaste and wondered what it would have been like if he hadn't just brushed. I was now making out for the first time, and it seemed like it was with a girl – and I loved every moment of it!

"Wow!" said Chris, "Men have kissed me, but nothing like that!"

"Chris," I said, "This is all so new to me, but I really like you this way."

"You do?" Chris said, "I was so embarrassed when you saw me at the door, but I like being with you this way."

Chris agreed to spend the rest of the day with me as a girl. We had a lot of time to talk in ways we never had before and made out whenever we felt like it – which was pretty often.

I became fully aroused again and found myself wanting another blowjob, but also thought about taking care of Chris.

As we kissed I told Chris that I did want to "Return the favor" if he would like it.

"I've never been on the recieving end," Chris admitted, "But sure have wondered about it – the men I've blown all really seemed to love it!"

"I've never done it before and I'm not sure I can," I said.

"You mean you're not sure you have the skill, or not sure you are really willing to?" asked Chris.

"Either," I replied, "Or both – oh I don't know – this is all so confusing!"

Chris kissed me and out tongues danced together. "I don't want you doing anything you don't want to do," Chris replied.

"What you did for me was amazing!" I said, "And I sure want more, but want to do it for you too."

In all ways it really seemed like Chris was a girl, so I decided think of her that way.

I reached under her skirt and felt the soft warmth of her inner thigh. Feeling adventurous I continued and soon felt the bulge in her panties. I rubbed it as she kissed me more passionately. It felt like her tongue would go right down my throat.

I reached my other hand under her skirt and pulled down her panties down, exposing her erection. I brought my mouth to Chris but hesitated. I knew this wasn't something I should be doing, but I really wanted this, and bent to her, taking her into my mouth. In my arousal I just desired her more, and explored her with my tongue, encouraged by her moans of delight. Soon she squirted her load into my mouth. It was strong tasting, different from anything else. I wasn't sure I liked it, but was glad to receive it, and eagerly swallowed.

"Jeremy, that was even better than I'd imagined," Chris said, "Thank you so much."

"I wish you could be a girl all the time," I said.

"Me too, but I'll have to change back soon," she said, "My father will be home soon, and he likes me as a boy."

"I guess we better keep this to ourselves," I said.

"Just one more thing before you go," Chris said, unzipping me. Soon she was sucking me again and I soon came. She swallowed and stood up. I pulled her to me and kissed her, forcing her mouth open. From that point on we always kissed like that after sucking each other off.

I left, looking forward to seeing girl Chris tomorrow.

For the rest of the summer I spent as much time with girl Chris as I could. We spent some time with Chris in boy mode, and I found I wasn't the least bit attracted, but was always glad when he would dress for me. Once school started Chris had to be a boy all day but had blowjob appointments many days right after school. On the other days Chris would dress for me, and I always made sure I took good care of her.

By October Chris had appointments nearly every day, so I went a long time without seeing her as a girl. Weekends Chris remained a boy because his father was home. I hung out with Chris in boy mode, and we lamented not being able to be intimate.

"I think it's especially difficult for me," said Chris, "Because you look the same to me if I am dressed or not, and really miss going down on you."

I missed that too – it was so much better than jacking-off, so we went into a nearby wooded area and I unzipped. Chris knelt and sucked me off. I closed my eyes and imagined Chris as a girl and soon I came in my mouth. I had forgotten that we always kissed after a blowjob, and was surprised when Chris stood up and kissed me. The idea of a guy kissing me was gross, but I missed that special kiss, so I closed my mind and imagined girl Chris.

We did that for a few days, but it bothered me that it was so one-sided. I wasn't at all attracted to Chris as a boy, but really missed sucking her. I asked Chris to hold my load in his mouth while I sucked him off, then we kissed (eyes closed for me), and mixed our loads, and each swallowed the mixture.

Though I missed Chris as a girl, this arrangement worked out well for both of us. I looked forward to summer, and being about to spend the day with Chris as a girl.

Then my world fell apart. The police raided Chris' house and arrested her father. Chris was taken to a foster home and I couldn't find out where. I found myself crying and realizing that I actually had come to love Chris, and it hurt so much to lose here.

After a couple of weeks I began to wonder what it would be like to blow other guys. With Chris out of my life I would jack-off a lot. It wasn't as good as a blowjob, but it worked. I found myself thinking about sucking other guys and would spend a lot of time looking at cocksucker porn. I decided that I had to find someone to suck.

A few days later at school I was taking a leak in the boy's room and there was a guy standing at the next urinal. I tried to get a look at his cock, but the modesty screen blocked my view. I stepped back to get a better look. The guy noticed me looking and said, "You like this?" I nodded and tentatively reached toward him but paused.

"Go ahead," he said, and I took him in my hand and felt him grow as his arousal mounted.

"Suck it," he urged, and I needed no further encouragement. He came with me to the end stall, where I sat down as he stood before me. I took him into my mouth and ran my tongue over him. The shape was a little different than Chris, but still familiar, and very welcomed in my mouth. Soon he came in my mouth and thanked me. Pulling out, he left and I held his load in my mouth, enjoying the taste.

As much as I enjoyed sucking Chris, there was something very exciting about blowing a total stranger! As I swallowed, I realized that since I didn't know this guy, I had no way to connect with him again. I considered trying the same approach to find other guys, but realized I'd been pretty lucky – some guys could be offended and beat me up. I also needed to be discrete – I hoped that the guy I just blew would be discrete but could only hope for the best.

I finished out the day wondering if I'd ever blow that guy again. The next day he approached me at lunch and had two friends with him. We talked briefly and I agreed to blow all of them as long as they kept my secret. They all agreed, and I agreed to meet them after school in the parking lot.

After school I got in his car with his friends and we drove down a country road and parked near a bridge. We got out and went under the bridge, where they all unzipped and took out their cocks. I dropped to my knees and began to suck. The other two guys stood on either side of me and I handled their cocks, getting them ready for their turn.

I sucked him to completion, and then the other two. I gave them my cell number so they could contact me for more, making them promise to keep my secret.

I realized that they told others when I got blowjob requests from other guys I didn't know, and I gladly blew them all, a little worried about my secret getting out. By the time summer break came along I had over twenty "regulars". Some were more regular than others – one guy wanted it nearly every day, while others a few times a week. The others were once or twice a month, but I was thrilled to be sucking that much.

I still think of Chris fondly, and hope that he is well – I've dated a few girls, but none were as good as Chris. I knew I would never be happy with any other girl, but as long as I could blow guys on the side it was okay.

Now, in my twenties, I'm married and still blow a variety of guys, and occasionally connect with a cross-dresser. I'm always eager to get their panties off so I can suck them! Then I go home and kiss my wife!

  To be continued . . .

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