First Taste of Cum Part 439    
          by Bill Beaumonte (oral_guy_2000@yahoo.com)  



This work 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.


Pretending

    I 'm Tina, though I used to be Tim. I was born a boy and was pretty happy that way, but as Tom, my older brother approached puberty, I saw that boys were horny all the time, with the hots for girls, but girls just didn't play fair. They rarely cooperated, leading the boys on and often leaving them unfulfilled.

I realized that while guys may technically run the world, the girls control the guys by regulating their access to sex. I envied them the control they had and wished I could be a girl. Don't get me wrong – I'm not at all "gender dysphoric" – unhappy about being a boy, or feeling I was a girl born into a boy's body. I had no desire to lose my cock – I liked it a lot.

But as I thought about it, I realized that some people born as boys transitioned to living as girls. Some had surgery to turn their cock into a pussy, but that was something I wanted no part of. I learned that some lived full time as girls while retaining their male equipment. At the same time, I found myself watching a lot of gay porn, and really got turned on thinking about cocksucking. I reasoned that if I was a girl (or at least passed as a girl), I could find lots of cocks to suck and be quite popular!

But how to start? I decided to start by wearing panties and set myself up to get caught by my family. Then I would fake being gender dysphoric and convince them that I was really a girl inside. I read a lot of stories about trans-women who started out as boys, so after a while I knew how to fake it.

I went to the local Walmart and bought some pretty girlie panties. They felt wonderful – so soft on my sensitive parts! I had to buy several different sizes before I found the right size for me, but I wore them all the time instead of my drab boy's underwear. Becoming a girl was going to be a lot of fun – they had so many sexy clothing choices, and I looked forward to arousing the boys.

I'd been wearing panties for about two weeks before my mom noticed anything. She didn't see me in them but noticed that I didn't have any underwear in the wash. I washed my panties in the sink because putting them in the laundry would be too obvious. My mom asked me if I was going without underwear, since I had a drawer full of clean ones, and none were in the wash.

Pretending to be ashamed, I said, "Mom, I have a secret I've been afraid to tell you about."

"Now Tim," assured Mom, "You can tell me anything – don't be afraid to open up to me."

"Okay," I said, "I think I am really a girl. I know I was born a boy but just don't feel like a boy."

"When did this all start?" she asked in disbelief.

"I've always felt that way but kept it to myself." I said, "People like me need to keep it secret."

"No," Mom countered, "People like you need to be loved. I think we need to get you to a specialist on gender issues. Meanwhile, let's keep this between us – your father is going to have a tough time with this."

My ploy was working, so I just needed to stay the course and not mess up.

A few weeks later Mom took me to a therapist who asked me lots of questions, which I carefully answered as planned. Perhaps I might have a career in acting in the future, because I pulled it off, and she diagnosed me with gender dysphoria and recommended that I be allowed to dress and live as a girl. We talked about hormone treatment, which I hadn't given much thought to, but agreed to consider it. I knew for sure I didn't want surgery – I sure like my cock – it was my best friend!

I asked Mom what she thought about the hormones and she told me that if I did, I would develop breasts and soft skin like a girl, but if I didn't I'd develop male characteristics, like facial and body hair, and an adam's apple. I'd be a pretty homely girl if I didn't take hormones, but possibly a pretty one if I did. So I decided to try the hormones, and the therapist referred me to a doctor, who Mom took me to. I left with a prescripton for female hormones and a testosterone blocker.

The testosterone blocker would prevent my developing male features, but would also keep my cock small. That was okay – it would still work and would be easier to hide in a swimsuit. I began taking both on a daily basis but didn't notice anything for about a month. Then my nipples began to get sore, which the therapist had warned me about. It signaled that breast development was beginning. I learned that I could expect to have breasts nearly as big as my mom, which would definitely attract the guys.

We reached the end of the school year and started summer break. It wasn't until then that I began to dress fully as a girl. But before that, we needed to tell the family. Tom was completely surprised, but seemed somewhat accepting, but my dad went ballistic. He called me a filthy faggot and said the no son of his was gonna go around dressed as a drag queen!

I tried to reason with him, which earned me a hard slap across the face, which left me crying. "Yeah, go ahead and cry, you sissy faggot," he said, "I guess I'll have to make a man out of you yet."

That was the beginning of the end for Mom and Dad. While I don't regret becoming a girl, I do regret busting up their otherwise happy marriage. They fought a lot – often about me, but also about other stuff – I may have been the catalyst to show them they weren't really fit for each other.

At the end of summer Tom went out of town for college, so he escaped the hostility at home. Dad would sometimes smack me around, saying it was all my fault – that I'd spoiled everything. By the next summer it was really tough to endure life at home. Then Tom contacted me with a suggestion. He suggested that I come to his college town, and he would help me find a place to stay and a job.

That was perfect! I really needed to get out of the hell I was living at home. I packed a few bags of girl things, left a note for Mom, and went to the bus station, where I took a bus to Tom's college town. I called him on the way, completely surprising him, but he agreed to meet me at the bus station.

It was just about noon, so he took me to lunch and took me around to apply for jobs. That's when I discovered a major problem – my school ID and my birth certificate (the only legal identification I had), showed me a Tim, and a boy. I'd never be able to get a job without ID that at least matched who I said I was. Without a job I couldn't pay for a place to live, so it looked like I'd be homeless.

Tom tried his best to help, but didn't have enough money to cover my living expenses. I began to cry and Tom hugged me, trying to console me. I feared I'd have to return home, when Tom came up with a solution. He explained that many of the guys at his fraternity house had gone home for the summer, leaving only sixteen guys remaining. He said I could probably stay there for the summer, while we worked out what to do next.

Tom took me to the fraternity house and rounded up all the guys, introducing me as Tina (he was such a great brother!). When he proposed my staying there for the summer most of the guys smiled and seemed pretty agreeable, but there were a couple who disagreed.

"This if a boys-only house," one guy said.

"But girls sleep over routinely," countered another.

"But that's just an overnight – not ongoing."

It was getting kind of messy, so I made a bold move, saying, "If I can stay here, I'll give blowjobs to any of you whenever you want."

Tom looked at me in horror, saying, "Wait, you need to think this through."

I insisted, and asked the boys to vote. They did, and I was accepted 15 to 1 – Tom was the only "no" vote. Even the guys who initially opposed my staying voted for me once I offered blowjobs.

"Just a couple of conditions," Tom insisted, "Tina stays in my room and she only does blowjobs – she stays a virgin."

The guys agreed, although I wasn't sure I liked Tom's conditions. He told me to follow him to our room so I could get settled.

Once the door was closed, I asked why I was staying with him and why the virginity requirement.

"They think you are a girl, and as long as you keep your panties on, they won't have any reason to suspect otherwise," he explained.

That sounded reasonable, and I appreciated him looking out for me. Then I surprised him by confessing, "I never gave a blowjob before – will you teach me?"

"You promised to blow all the guys and you've never done it before? What were you thinking?" he asked.

"I was deperate and needed a place to stay – besides, I've been wanting to give a blowjob but the boys back in school would have nothing to do with me, knowing that I used to be Tim."

"I'm embarrassed to admit this, but probably should," Tom said, "But I think you're really hot and think about you a lot."

"When you jack-off?" I asked. Tom paused, turning a bit red, "Go ahead and admit it – it's okay." Tom just nodded, but I wrapped my arms around his neck and kissed him. He didn't resist, but tried to play it cool, until my tongue parted his lips and we French kissed. Then he really got passionate. I put my hand on his pants, feeling his cock harden underneath.

"I think it's time for my blowjob lesson," I said, unbuttoning my blouse. I removed my bra, exposing my small A cup breasts. They weren't big, but were definitely breasts and as I approached Tom, he proceeded to feel me.

I dropped to my knees and fumbled at his zipper – working from this perspective was entirely new to me, so he helped, and soon his cock was out, and semi-erect. I took him into my mouth and marveled at how well it fit – like cocks and mouths simply belong together! I looked up, making eye contact, as Tom smiled at me. He instructed me about keeping my teeth off the cock and how to move my tongue around. It seemed like a lot to learn, but I was eager. Soon he came, dumping his hot load in my mouth. I'd dreamt of this for years and now had my first taste of a man's seed, and knew I wanted more – a LOT more!

Tom told me I did really well, and shouldn't hide my lack of practice – the boys would give me plenty of that. I told Tom that I wanted to blow him as often as possible to hone my skills. We fell into a rhythm of my waking him each morning with a blowjob, and giving him one at night, just so he could sleep well.

The other guys at the fraternity house were eager to get started with me, and before the end of the first evening I'd blown all of them, feeling a little nauseous. I was learning that while cum may be safe to swallow, too much could cause stomach upset, and even vomiting. Throwing up was a lousy way to end a blowjob so I did some online research to see what could be done. I learned that everyone has a "limit", which increases with practice. Until then I would have to avoid doing a lot of blowjobs in a short time, so I needed to space them out. That wasn't a problem, since the boys stopped by at different times on their own.

As my experience grew, I encouraged the boys to come back a second or third time, and soon most of them were getting both morning and evening blowjobs. It was a rare day that I didn't give over 25 blowjobs. I was a pretty happy girl!

Then I learned that they were planning a party to attract new members and wondered if I would be willing to work a suck line. I had no idea what that was but was told that I would simply be on my knees sucking, with guys lining up behind, each awaiting their turn. It sounded great, and I agreed. I jacked-off, pulling my little boy cock to climax as I thought about the suck line. On the day of the party I was asked if I would do the suck line naked, because it would arouse the boys more. I balked – if I was naked they would see that I wasn't a real girl and who knows what would happen then?

Fortunately, Tom came to my rescue and suggested that I wear a pair of thong panties, so I could tuck, but be nearly naked, with my ass fully visible. He took me to our room and helped me get ready. It took some doing to tuck without showing a bulge, and I had to use some bandage tape to do it well, but soon we both liked the look, and Tom insisted on a blowjob right away, which I was glad to do, but then he took me into his arms and began to kiss me. Kissing Tom was so special – I was so thrilled that he wanted me! All the other boys kissed me a lot, but this was a first for Tom. He fondled my bare ass while we kissed and then turned me around and dropped to his knees to begin kissing first one cheek, then the other.

"You have such a hot ass!" he said, now growing more adventurous and licking my crack. This was a side of Tom I'd never experienced, but I sure liked it. He continued to surprise me by spreading my cheeks and licking my crack. After a few licks he pulled the thong strap aside and kissed me directly on my hole – it was incredible – not just that anyone would do such a thing, but that it felt so wonderful!

I moaned with pleasure, making sure Tom knew I loved it. Then I felt Tom's tongue pressing inside me, causing my little cock to become fully erect, and nearly breaking free from my panties. Tom continued making me completely lose control from hyper-arousal. I pulled away and turned around, slipping my cock out of the panties and pressing it into Tom's mouth. I would ordinarily never have done that, but I was swept away by lust and unable to behave rationally. To my surprise Tom didn't resist, and began to suck be eagerly. It only took a minute for me to cum, which he took in his mouth without protest.

Once I came, the gravity of what I had done hit me. "Oh Tom," I said, "I'm so sorry – I just couldn't help myself!"

"It's all good," he replied, "I've been wanting to go down on you for a long time, but never quite got the nerve to do it, but your hot ass was more than I could resist. I want to do that a lot more, and maybe have you as my girlfriend?"

"Tom, you are my hero!" I replied, "You've made all this possible and I would be delighted to be your girlfriend, if you can get away with dating your sister."

"That won't be a problem," Tom assured me, "We'll keep it secret. When we go out, I'll take you far enough away so we won't run into anyone we know. It's no problem sharing a room because everyone thinks I am protecting you, which I am."

"But I have to continue to blow the other boys," I said, "In order to earn my keep."

"No problem," Tom confirmed, "It's a promise you've made. Anything else?"

"Just one thing," I stated, "If I'm gonna be your girlfriend, I want you to make love to me."

"It's as good as done," Tom promised, "Tonight will be the first of many!"

I confided in Tom that I was a little nervous about tonights work. We were expecting a number of new students who we wanted to interest in membership, and I wanted to do my very best for them. I was worried about the volume of cum I'd be swallowing. When I started sucking, I found that I'd get nauseated if I swallowed too much, too soon. Since then, I've done a lot of swallowing, and I was sure my "limit" had increased, but didn't know how much. The last thing I wanted to do was to throw up after blow a guy – that would be horribly rude indeed!

Tom and I agreed on a signal. He would be standing by, and when I gave the signal he would call for a break after I finished the guy I was doing. It might seem strange to have your brother watching every blowjob you give, but after all – he is my lover.

It all worked out well. As soon as there was a hint of stomach upset I signaled, and soon I'd be taking a break in our room, with Tom doting over me. He had me take an anti-nausea medication and lay down for half an hour, after which I was eager to continue. With three breaks that night I blew 57 boys, and swallowed every drop that entered my mouth!

After the party was over I cleaned up for bed. Blowjobs are generally quite clean, but a couple guys pulled out and gave me facials, which seemed to be a terrible waste of cum, but for some guys it's a real thrill. I wanted to be clean and pristine for Tom. After a nice shower and a few dabs of perfume, I slipped into a sexy nighty and climbed into bed, where Tom was there ahead of me. He immediatley drew me close to him and kissed me, parting my lips with my tongue – I was glad to have brushed after all that cum!

He surprised me by taking hold of my little cock and squeezing it – that really ratcheted up my arousal!!!

"I want you to have my virginity," I told Tom, "But I'm afraid it will hurt."

"The way some guys do it, it sure does," agreed Tom, "But I want this to be a night of delightful memories for both of us!"

With that, Tom rolled me onto my stomach and proceeded to spread my cheeks and kiss me deeply. That was such an amazingly wonderful feeling, and a really great way to warm me up! Next I felt something cool and wet between my cheeks, which was Tom's lubed fingers dancing at my entrance. He slowing slipped a finger in and just held still. "Is that okay?" he asked.

I tightened around his finger and replied, "Better than okay, Tom, please have your way with me – I trust you completely!"

Tom slipped his finger in all the way, wiggling it about – I'd never felt anything quite like that before! Then he pulled out and pressed two fingers in, slowly at first, then all the way. He wiggled them back and forth and I was in heaven!

He spread his fingers to open me up and seemed to just know how much I could take. I felt myself stretching, but there was no pain at all. Tom added more lube as he slipped in a third finger, spreading all three to complete prepping me.

He pulled out and slid his hard cock between my cheeks, pressing against my entrance. Slowly he entered, and I was thrilled to feel him completely inside me without a trace of pain! I was on my back with my legs up Tom's chest – he held me close and played with my little cock as we made love.

I tightened around him and he told me I could do that all I wanted. Tom slowly began to slide in and out of me. As he did, I tightened each time he pulled back, as if I didn't want him to slip out. After about 25 strokes I tired and couldn't do it any more, but knew I would have to practice and build up my stamina – I wanted to be the best fuck Tom ever had.

Tom was wonderfully gentle but gave me the ride of my life. Tom stroked my cock, and soon I came, squirting all over my belly. I learned that during climax, the anal sphincter tightens and loosens about once a second, so Tom could feel me cumming, and that sent him over the edge. He pulled me close as he gave me his seed.

We remained there, coupled as we caught our breath. We gazed into each other's eyes and I felt completely in love – not the kind of love you might have for a sibling, but real, romantic love. I knew this was extremely taboo, but I wanted all I could get of it!

Special thanks to my online friend Scott, who provided the inspiration for this story

  To be continued . . .

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