During the usual summer visits to all my family members, Paisleigh decided to cater to my fantasy this year. My rationalization of this particular kink is that i find girls the most attractive when they aren't trying, and girls are the most natural and beautiful to me when they sleep.
To try this kink, Paisleigh waited until everyone else left, and i was sleeping, so she came into Robby's bedroom and pulled my dick out of my shorts and boxer briefs, and slid her wet, tight pussy down on my dick. Waking up, i slowly got into her movements enough to roll over on top of her to pound her pussy instead. We barely managed to cum, with my cum filling her pussy, and hers soaking my dick, balls, and mound before we could hear my cousins come back to gripe about how late i always wake up. Paisleigh then invited me to wake her up the same way if i got horny at night.
This left me horny all day, but not willing to waste my energy before fulfilling my fantasy. After everyone else went to sleep (i'm almost always the last to fall asleep), i went to Jocelyn's bedroom. Then, i pushed Paisleigh's shorts to the side to rub her clit through her panties until she soaked them. Then i spread her legs, pushed her panties to the side, and climbed on top of her before taking out my dick and penetrating her as slowly as i could. Before i could even work my full penetration into her pussy she woke up. She wrapped her legs around me and pushed me into a sitting position for us to mutually f*ck each other into submission.
Thankfully, this year, she seemed a little less needy and attached, so i didn't have to make the expected reminder about not getting too emotionally attached to the idea of settling down with me.
Speaking of never settling down, i also worked in some time this year with my friend Melody. i remember during this time in my previous life, she was quietly dating a football player, but when i went to visit her at her house it didn't take a lot to get into her pants. A few kisses on her lips and neck, and she was ready to give a blowjob. i stopped her and offered to go down on her instead, but she just wanted to get to the action. She told me to lie down, unbuttoned and unzipped my pants and pulled out my dick, and took off her pants and panties to ride my cock to messy completion in her pussy. Then when she was getting up, i moved behind her and pushed my dick back into her pussy in doggy style to f*ck her harder and finish in her again. After the usual discussions and "plan b" pills, she let me know that i had to schedule any future visits but that she was usually down to play again.
The situation with Julie didn't move as quickly; she was typically so verbally combative that she didn't stop her outward hostility until i started feeling her up for a few days on the bus before school. Since this was fall, and early mornings were cold. We were wearing sweaters that made it easy to rub her tits under her sweater, but at first over her shirt, then under her bra before wiggling my hand down her panties to rub her clit. After a few days of forcing her to quietly cum on the bus, i invited her to my usual visits at my house by the school.
When she came to the house, she quickly pushed past the typical lead-up to taking off clothes and promptly took off my clothes before i caught up to take off hers. She then pulled me on top of her and led my dick to her pussy. When i thrust my dick into her pussy i was surprised by her virginity. However, she was wet enough that my typical slow penetration did not cause a noticeably painful reaction from her. Then she got frustrated by how slow and gentle i was being; she rolled over on top of me to bounce faster and harder on my dick. That was when i noticed her blood on my dick. This time when i tried to play with her breasts and clit, it just annoyed her since she was already frustratingly horny. With her frustration, i finally figured out that she wanted a bit rougher sex, so i led her to all fours and rammed my dick into her doggy style. After i finally started pounding her pussy, she came quickly, and while her pussy clamped down on my dick, i got to slow down and fill her up.
This experience showed some of the issues with sleeping with virgins, for not knowing what they want or how to get it. This is also one of the most common situations that i had to deal with originally, since my preference for softer sex conflicts with the more common preference for rough, aggressive, and/or possessive sex. Most girls would have tried to find a more aggressive/possessive guy at this point. However, working around our preference mismatch was still easier than dealing with the judgemental attitude of rural people. Julie later came to the house before games for more quickies whenever she got horny.
When Ricki got into a fight with Tessa and invited me to her house, i took a few chances to "accidentally" touch her. Then, when we went to ride her 4-wheeler, i let my hands "slip" to her nice-sized breasts and upper thighs. Then i directed her to the woods to grope her breasts and then rub her clit to orgasm before we even got off the 4-wheeler. Then i led her to prop her hands against a tree while i pulled her panties down. Then i went down to lick her pussy enough for her to be wet enough to penetrate and used the lube i brought when she invited me to her house.
Then i slowly penetrated her virgin slit as softly as i could before ramming through her cherry. While she was recovering from the shock, i rubbed her clit and nipples under her shirt and bra; until she was ready to continue. Then i continued down the soft and gentle sex that i prefer while constantly edging her towards orgasm and breaking the steady rhythm and stimulation. When i finally came in her pussy she was so frustrated that she repeatedly came from the rougher penetration right after. By the time i finished cumming in her for the second time, she could no longer stand and was a shuddering mess.
When Julie and Ricki argued about who sat with me on the bus the following day, they instead sat together and talked about fucking me. This led to Julie learning that if she treats the first round of sex like foreplay, then i would gradually get closer to her preferences without prompting. This led to her deciding to let other girls fuck me first when there's a scheduling conflict, as well as her showing more tolerance instead of impatience.
Ricki and Melody filled most non-game days this year with requests to fuck, but next year would get more restrictive when Melody's brother moves here, and Ricki moves away. Julie stuck to just visiting for quickies and sloppy seconds (or thirds) when the other girls were busy getting ready for their games.