Tuesday, January 12, 2016

Country Bumpkin

Billy grew up on a farm pretty much his whole life, but felt like he had to leave. He decided to leave for the city to meet new people and have new experiences. He moved into an apartment complex that was full of sexy women. However, none of them were interested in him, for they saw him as a country bumpkin - a farm boy with no money.

He did, however, meet a friend. It was the boy who lived across from him named Kerry. They met for meals at times, and he expressed his loneliness to him. Billy told Kerry about his strikeouts with the ladies in the building and in the city. Finding so many sexy women around him only made his lustful desires grow. But not being able to satisfy his desires made him incredibly frustrated. Kerry told him that he felt the same way, but that he had found a way to satisfy his desires to some extent. At first, Billy thought that Kerry would tell him about prostitutes. When Billy asked what Kerry's way to satisfaction was, Kerry told him that it was all about masturbating in the right way. Billy didn't know what masturbating was, despite being in his late 20s. Kerry was surprised, but awkwardly explained what masturbation was. Both were a bit uncomfortable. You see, Kerry and Billy were both heterosexual, or at least found themselves incredibly and sexually attracted to sexy, feminine women, and women only. Billy was nevertheless intrigued. He then said what this special way of masturbating was. It seemed like all masturbating involved was stroking one's hard cock until ejaculation - simple. Kerry explained, a bit hesitantly, that he had bought women's clothing and lingerie - dresses, wig, makeup, heels, etc. - so that he could dress up like the sexy women in the building. He would then have "his way" with himself.

Billy laughed in surprise. "You put on a dress and do this thing called masturbation and pretend that you're one of the ladies? HA!" he laughed. He thought he had seen it all. Kerry was a bit tussled by Billy's scoffing, so told him that he would show him. He went into his bedroom and got all dresssed up. He put on some charcoal patterned pantyhose, put one makeup and a wig, and then some jewelry. He topped it off with a body-con short mini dress. He slipped into some high heels, and he completed becoming a she!

When Kerry came out, she said "Check it out! Not bad, huh?" Billy couldn't believe his eyes. She looked just like one of the hot women in the building. He was silent, wide-eyed. He got up and walked around Kerry. Kerry just stood there mockingly doing feminine poses with a lighthearted, self-satisfied smile, like she had proved Billy wrong. What she didn't know, though, was that Billy was getting a lot more interested than Kerry would have ever thought. You see, Billy was starting to see Kerry as a woman, and Kerry had not yet realized this yet. To her, they were still guy friends, buddy neighbors. 

"Wow, turn around", Billy said to Kerry. Kerry obliged. After Billy stared at her pantyhose legs and ass, he asked "So you just stand there and do this mastur-thing?" Kerry said that she didn't, and proceeded to the couch. She got on the couch on both knees, facing the couch back. She bent over and said that she likes to do "this" and watch her ass while she masturbates. Billy watched her bend over listening to the dress stretch around Kerry's ass and creep up her pantyhose covered thighs. He walked over behind Kerry as she was bent over, and placed his hands on her ass.

"Ummm...what are you doing Billy?" Kerry asked. You see, she wasn't trying to turn Billy on, or in any way seduce him. That thought didn't even cross her mind. For all she knew, she was just teaching Billy how she satisfies her frustrations, only so that Billy, if he should so please, can do so himself with his own clothes. But now she felt Billy's hands fondling her ass, thighs, between her legs, etc. She was surprised to find that she liked the feeling. They were both silent, Billy fondling her and Kerry feeling his caresses. She turned around and saw that Billy's slacks had a huge bulge in it in the crotch. She bent over slightly more, and pushed her ass back a little to lightly touch Billy's crotch, just enough to gently feel something hard and throbbing.

His hands moved up her legs and ass, and found her waist. He gently put his hands around her at the waist, and then moved forward, pressing a little more slightly his crotch to the crevice that had formed by the dress stretching over Kerry's ass. As he did that, she could feel her pantyhose slightly stretching where he pressed around her ass crevice, but she suddenly felt a hard throbbing stretch in her pantyhose right around her crotch. She was turned on. She not only was looking like one of the women in the building, but was starting to feeling like one.

"Ow, my goodness, ow" moaned Billy. Kerry asked him what was wrong, and he said that his dick hurt because it was so big. "Should I do this mastur-what thing now?" he asked. Something came over Kerry, and she said "I have a better idea. Slide up my dress". Billy did so, slowly, with trembling hands, exposing Kerry's pantyhose clad ass. He could feel the heat and moisture from Kerry's hot crotch come up to his face as soon as he exposed it. He stared at her ass through the sheer tights, and could faintly make out her butthole. Remaining in position, she looked back at Billy, and unzipped his slacks. "Pull it out" she softly ordered. Billy barely had to do anything, for with the slightest move, his hard shaft sprung out, like a fleshy pole engorged with a lustful throbbing that he had never experienced before. "Ow, it really hurts" he said. It just stuck out in the air, pulsating and engorged, hard as a lead pipe. He grabbed it like a bat and started to stroke. Kerry saw him stroking as she had instructed earlier before. "How's that?" she asked. Billy had a look of pain and impatience in his face. "It's making it worse. It really hurts. It's hurting more every time I look at you. You look too much like a woman". Kerry then suggested using the lotion next to him. Billy pumped a generous portion on this hand, and began gliding it along his shaft. "How's it now?" Kerry asked, still bent over. "It's making it worse, Kerry, I don't know what to do. I think I'm too turned on"

Seeing how much Billy was turned by her femininity was turning on Kerry. Her own 'clit' was rock hard and throbbing, and her crotch was glistening with anal sweat and juices from her hole under the pantyhose. Billy could smell her juices. He could smell her hole, and for reasons he didn't know, he was getting incredibly turned on by the scent. 

Kerry finally reached around and tore a hole in the back of her pantyhose. The tear made a rip sound, and her was totally exposed. She could feel the cooler air kissing her ass and especially her butthole. The heat and smell hit Billy, and he became dizzy with wild lust. "Slide it in" she said softly. Billy didn't know what she was talking about. "Slide what in where?" he asked. "Ow, it really hurts. "Slide in your cock into my butt." 

Billy was shocked, but then grabbed his throbbing, sensitive shaft and positioned the engorged head against the wet, glistening anus. He pushed slightly, but it didn't go it. "I don't think it's going to fit". But before he could finish, she pushed back, and the engorged head popped in and the rest of his pole just slid in smoothly. "Oooooohhhhhh myyyyy..." Billy moaned. She gasped and moaned. "Ooh, yes, that feels so good - that feels toooo good" he moaned, as he slid his pole slowly in and out. "How did you know....oooh...that this would help....oh my goooooodneesssss!!! How did you know your butthole.......ohhhhhh....would....help....." He looked down and he could see her wet anus stretched around his fleshy pole, making it glisten with the juices in her ass, pulling ever so slightly when he slid out, and pushing in ever so slightly when we would slide in. He kept pumping her. He couldn't believe the sensation. Her as was so tight around his hard shaft that it was mixing the throbbing pain he felt with an incredible ecstasy. "Yesss, that's it. Just like that" Kerry said. "Does it feel good now? Does it still hurt?" "Oh, it feels too good. This is what I needed...Ooooh" Billy moaned. Kerry's rock hard clit was bouncing in the air with every pump of Billy's cock. Her cock was dripping and oozing with cum, sprinkling it all over the couch. Billy's cock was so hard and so big, and it was gliding in and out of her anus with such grace, that eventually she squirted all over the back of the couch. Billy kept going and then became frantic. "Oooh my....something is going to happen! something is going to happen! something...is...oooh". He kept pumping, and now, with each pump in, his cum oozed out of the stretched sides of anus. Billy came with an explosion inside of Kerry.

Billy never would have thought that Kerry's secret trick in satisfying frustrated desires would have worked so well. He was puzzled how Kerry could have thought that sliding his pole into her butt would have made the pain go away and make things good - very good. What an experience for a country farm boy like Billy. It looks like Billy will never be going back to the country again.