Sissy Gurlfriend Part 1
Sissy Gurlfriend Part 1
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:
_A high school guy finally finds dating success with an unexpectedly different girlfriend. I hope you enjoy this work of fiction.
_
I 'm Bill, a high school junior who had marginal success in dating. I really like girls, but they can be really difficult. It's hard to know what to say when we talk, and it's tough to get very far with them.
It's not hard to get to kissing them, and with a little patience I can usually feel their tits, but then it gets more difficult. Getting a blowjob is nearly impossible. One insisted that I go down on her before she would even consider doing me. So I did, and nearly puked! I'm not sure if she just wasn't clean or if all girls smell like that, but I sure never want to even try again!
Still, I continue to try dating girl after girl. I'm not bad looking and could easily get first dates, and usually second dates. But if a girl doesn't seem at least cooperative by the second date, I move on.
One day new neighbors moved in next door. There was a guy named Ken who was a high school senior, and his sister, Kerry, who was in my class. She really looked great, so I knew that sooner or later I'd be asking her out. Ken and I hit it off really well, which surprised me, be because he was older and had a car. It was August, so school wouldn't be starting until next month.
We hung out together most days and I got acquainted with Kerry. I felt really confident that she would go out with me, but one day I asked Ken if there would be any problem if I asked her out. I didn't want to create an awkward situation between us.
"Actually, Kerry doesn't date," Ken said.
"Why not?" I asked, bewildered.
"She's had some bad experiences in the past," Ken explained, "One jerk actually beat her up pretty badly."
"What kind of asshole does that to a girl?" I asked, "You know most guys aren't like that, and some are pretty good guys."
"You mean like you?" Ken asked with a smirk.
"Well, yeah," I agreed.
"I don't have a problem if you ask her," he said, "But don't get your hopes up."
I knew I'd have to make a really good impression on Kerry, so decided to ask my mom for some advice. I'd never done that before, but Kerry seemed really special, not just another opportunity for some nooky. Mom was happy to talk with me and said she was glad that I was finally starting to get serious about girls, and not just looking for someone to put out.
Mom really stressed that I listen – that seemed obvious enough, but she made a point of saying the most guys don't REALLY listen. She also warned me about not trying to fix problems, when a girl really just wants someone to listen.
It seemed like she was splitting hairs, but I listened and tried to comprehend her. For sure girls think a lot differently than guys.
One day I saw Kerry working in a flower garden in the back yard, and went over to talk. "Nice flowers," I mentioned.
"Yes," Kerry agreed, "The previous owners planted some really nice ones."
"Some of them look like they could use splitting," I mentioned.
"Splitting?" she queried, "What for, and how?"
I pointed at several flower clumps and said, "These flowers reproduce by spreading, and soon get crowded. If you dig them up and split them into smaller clumps you can plant the each and they'll continue to spread."
"You know how to do that?" she asked.
"Sure," I said, "I helped my mom do hers." Actually I didn't really help her much, but learned enough by watching her.
I worked with Kerry and soon we had all the clumps split and replanted. If felt really natural talking with Kerry – easier than with other girls. I was tempted to ask her out, but decided not to rush things. I wanted her to feel really comfortable with me before asking her out.
Over the next few weeks I saw Kerry nearly every day, and she began to ask for my help doing various things, like reloading the string in a string trimmer, and jump starting the lawn tractor. I prefer girls in dresses or skirts, but Kerry usually wore shorts when working in the yard. Those shorts really showed off her ass! I had a hard time staying focused!
Once school started I talked with Kerry most days after school. She said she was having difficulty with a school project, and I immediately remembered what Mom said about listening and not trying to fix things. So, I listened and just asked if she had any ideas for alternative ways to get the project done. That seemed to me like a pretty lame approach, since I had some great ideas to offer, but I held back.
Well, listening worked wonders, because once Kerry started to list different ideas she had, she quickly came up with a solution – just by talking it though. "You're not like other boys," she said, and kissed me on the cheek. That was really unexpected, but I wanted a lot more than a peck on the cheek. I knew I was moving in the right direction, though.
One day we had a bad hail storm, which damaged Kerry's favorite flowers. They had grown really nicely, but now they looked like they had been badly trampled. "I remember when we replanted these," she said, "And they grew so nicely, but now they're ruined!"
"They'll grow back next year," I said, but that didn't really console her.
The next day I picked up a bouquet of flowers for her at the grocery store. As I presented them to her she said, "Nobody ever gave me flowers before."
I just smiled and said it just seemed right for her. I knew that soon I could ask her out.
The next day after school I invited Kerry to join me for a latte at a nearby coffee shop. That gave us time to talk. After getting our drinks and sitting down, I began, "I'd like us to be more than just next-door neighbors."
"What exactly do you have in mind?" she asked.
"I'd like to take you out on a date and see where that leads," I replied, "Ken told me you are reluctant to date."
"It's not so much that I'm reluctant, but I've had some bad times," Kerry responded, "For a long time I thought all guys were jerks, but you seem different."
"For sure a lot of guys ARE jerks," I agreed, "But I hope you have seen that I'm not like other boys."
"True," Kerry said, "Unless you are just on your best behavior for now."
"I can't prove otherwise, so I guess you'll just have to see for yourself," I replied, "So how do I get you to agree to go on a date with me?"
"Well Bill, in a sense, I'm already on a date with you," she said.
I smiled and replied, "I'm glad to have gotten this far – I wonder if you kiss on the first date."
"That depends on whether you deserve it or not," she said.
"Then I will do my best to be deserving," I replied.
We talked about school for a while and what we were planning after we graduated. Now in our Junior year, we would be making application to universities. We lived in a major college town, so we both might be able to save some money and remain local, although going away for school had some attraction.
"We passed a nice park on the way here," I said as we finished our drinks, "Would you like to take a walk there?" Kerry smiled and agreed.
We arrived at the park and proceeded down a paved path into the woods. As we walked, Kerry took my hand. It was a small gesture, but to me it was electrifying! "I like holding hands," I said, and Kerry said she thought I would.
I hoped that one day soon I would have my hands on other parts of her, but for now this would have to do. We approached a bridge over a stream and paused to watch the water flowing. There were turtles floating in the water and dragon flies darting about.
There was something very relaxing about this, and we soon found ourselves looking into each other's eyes. The time seemed right and I brought my lips to hers and we kissed. As I pulled back I saw Kerry smile, so I went for a second, then a third. On the third time her tongue parted my lips and we kissed deeply as I pulled her close to me.
I felt her breasts pressing against my chest and hoped that one day soon I'd be touching them, but for now kissing was great. We continued to kiss for over a minute before disengaging. "Well, I guess you have your answer," she said.
"I sure like the answer," I said, "How about going to a movie with me on Friday night?"
"Only if I can get another kiss," she answered, "I think I'd like a second opinion."
I held her close once again, enjoying the kiss and the feel of her against me. I couldn't help my arousal, and soon had a raging hard-on. I hoped it wasn't obvious, but Kerry noticed and put her hand on my cock, squeezing it through my trousers.
She was definitely not like other girls! I always had to ask them to touch me, and Kerry was doing it on her own.
"I'm sorry," I said, "I can't help how I feel about you."
"Don't be," she said, "I'm delighted that you like me." Then she completely surprised me by unzipping me and slipping her hand in. As much as I liked it, I was really nervous – not knowing how to respond in this completely new situation.
Soon Kerry had my cock out and said, "Yes, you definitely have feelings for me!"
Before I could respond Kerry dropped to her knees and took me into her mouth. That was another first – I had never been able to talk a girl into sucking me, but Kerry just did it, and it felt wonderful! I realized that I would probably have to go down on her at some time. I didn't welcome the idea of licking a smelly pussy, but maybe she would be cleaner than other girls – I hoped so.
I was in complete bliss, but it didn't last long – soon I came in her mouth and she swallowed without hesitation. It was the best climax I'd ever had – far better than jacking off – I was in LOVE!
"That was amazing!" I said, "YOU are amazing!"
"I know guys have their needs," she said, "And I didn't want to send you home frustrated."
I helped her to her feet and kissed her. This time she kept her lips closed tightly. She pulled back and said, "Let me do a breath mint first." I realized she was sparing me the experience of tasting my own cum – another way Kerry was special!
I zipped up and we continued our walk. We approached another bridge and I took her in my arms again. We kissed, this time with open mouths – I tasted only the cinnamon flavor of her breath mint.
"Is there anything I can do for you?" I asked.
"Not right now," she said, "But perhaps another time."
We finished our walk, ending up at her door, where we kissed again as Ken greeted us.
"I see you've made some progress with Kerry," Ken said. I told him I was taking her to a movie on Friday, and he said I must have made a pretty good impression on her.
The next day at school Ken approached me and said, "We need to talk about Kerry."
"My favorite subject!" I agreed.
"Well, this is pretty important," Ken said, "Kerry asked me to talk with you about your date Friday night – there's something you should know."
"Is everything alright with her?" I asked.
"Yes," Ken responded, but there is something you should know – she wanted to tell you, but couldn't, and asked me to."
"What's that?" I asked, "Does she kill her dates?"
"Nothing that bad, but this may change your mind," Ken said, "Kerry isn't really my sister – she's my brother."
"What?" I responded, "You mean she's really a dude?" Ken nodded solemnly.
"She's only been on two dates before," Ken explained, and the guys freaked out when they found out – one beat her up pretty badly – that's why we had to move here."
"But she kissed so much like a girl – are you really leveling with me, or has Kerry changed her mind?"
"It's the honest truth," Ken said, "And she still wants to go out with you, if you do."
"But I'm straight," I insisted, but part of me still wanted to take Kerry out.
"So, let's assume the date is off," Ken said, "If you change your mind you can ask her again. But please, Bill, don't tell anyone – we need to keep Kerry safe from the bigots who would harm her."
I promised to keep her secret. I didn't want anyone to know I'd been kissing a guy anyway.
To be continued . . .
Feel free to contact me with your comments or requests.
–Bill Beaumonte (oral_guy_2000@yahoo.com)