Hank always thought his sister’s significant other Lisa was sexy. Even though she had an air ‘butchness’ about her. Lisa’s hair was done up feminine. She wore dresses occasionally to work and she used makeup. But she had a mannish way of walking and talking. She relished dirty jokes and just like men she made the occasional inappropriate sexual remark. She clearly was the ‘man’ of the relationship with his sister even though they both said that the relationship wasn’t about masculine/feminine stereotypes. Lisa was always in the man position during cuddling or snuggling. Eva, Hank’s sister, always wrapped her arms around Lisa’s neck during kissing. It their whole relationship it seemed that Lisa was the man and Eva was the woman. And Hank was jealous that his had found such a sexy and masculine woman.
Hank liked to fantasize that Lisa would make him have sex with her. Make him lick her cunt and suck hard on her small but perky tits. And for the finale, she would strap-on a dildo and stick it up his ass and fuck him til they were both exhausted.
Hank was a wimp and he had known this since he was little. He was always taken with the women who were masculine. He enjoyed watching women bodybuilders, they always turned him on. So Hank naturally thought of himself as the femme side of the equation and wanted to be with women who would be the masculine side. Hank loved to masturbate to fantasies about women doing him in his back door. From a young age he fondled and then eventually penetrated his ass. And from the first time he penetrated himself he knew that he would love a good ass fucking. When he moved out on his own he even bought a dildo to use on himself. He spent many a night in anal ecstasy picturing that a woman was giving it to him good. Now at the age of 23 he wanted a women to fuck him. Especially if the ass fucker was Lisa.
Lisa and Hank got along well because they were both big sports fans. She was a Giant fan and he was a Dodger fan. They would tease and mock each other throughout the baseball season. But since he had moved to SoCal a year ago they didn’t go to any games together anymore.
After a year in his new job, Hank finally earned a week’s vacation. He planned to go and spend a week with his sister and Lisa. He called his sister and made plans. Eva said she was happy to have Hank come up. She even mentioned that they would all go to a Giants game at the new PacBell Park.
When Hank arrived on a Saturday, the three of them spent the day wandering around town. They played a quick game of tennis in the late afternoon and then headed back to Eva and Lisa’s house for dinner. This whole time Hank couldn’t get the thought out of his head of Lisa fucking him with a dildo. And the way she was dressed didn’t help matters either. She wore a tank top with running shorts that showed her thighs up to where her butt started. Hank had to keep fighting a constant erection knowing he wouldn’t be able to do anything about it until bedtime.
When bedtime did come, Hank was finally happy he would get relief from the sexual tension he had been feeling since he had arrived. He bid a goodnight to his hosts who were also thinking of retiring for the evening. After brushing his teeth, Hank went in to his guest bedroom and quickly closed the door. He headed straight for his suitcase and found his dildo. From the side pocket he pulled out some lube and laid down on the bed. He fingered his ass for awhile fantasizing that Lisa was preparing him for a screwing. When he was ready, he slowly slid the dildo up his ass. He took his time savoring the feeling and letting his sexual imagination wander. He stroked his cock slowly, occasionally stopping to taste his precum. As the excitement built , he stroked faster. As he neared his climax, Hank moaned out Lisa’s name. “Fuck me, Lisa” he said a couple of times before finally releasing his load with an intense orgasm that made him what to shout with pleasure. He was able to somewhat mute his shout of pleasure and figured that Lisa and Eva probably didn’t hear it being that they listened to TV while they went to sleep. After resting for a few minutes, Hank got up, put on some shorts and headed to the bathroom to wash off the dildo. He came back to bed able to fall quickly into a deep sleep.
On Sunday, they were to go to the ballgame. But Eva found out that she was needed at work and wouldn’t be able to come along. So now it was just Lisa and Hank. Much like yesterday, Lisa was wearing very short shorts. Just looking at her legs while they drove to the game gave Hank an erection. Lisa seemed to be struggling with something on her mind as they drove the first few minutes in silence.
Suddenly, Lisa dropped the bombshell. “I saw you last night. I snuck into your room when you were brushing your teeth and hid in the closet. I was going to jump out and scare you when you got into bed and turned out the lights. But instead you jacked off with that dildo.”
Hank didn’t know what to say. He tried to mumble something. But Lisa continued.
“Do you want me to fuck you? You were moaning last night about me fucking you.”
Hank couldn’t look at her. He was caught and didn’t know what say. He figured Lisa was mad at him. “Did you tell my sister?” Hank finally asked.
“Yes and no. I told her I didn’t get to scare you because you started masturbating. But I didn’t tell her about the dildo or you moaning my name.” She smiled at him and added, “It’s called pegging.”
“Having a woman fuck a guy with a dildo is called pegging. At least in the circles I run in.” she smiled again. This made Hank feel much better. Maybe this wouldn’t be so bad. She at least seems amused by the thought. So Hank asked her if she ever had pegged a guy.
“No, but for the last few years it has been a big fantasy of mine. It seems it’s a big fantasy of yours, too.” She said as she looked at him with what Hank thought of as possibly lust. “Look in my backpack in the back seat. I packed especially for this trip.”
Hank did as he was told. In the backpack were two dildos and a harness to which either one could attach. “Which one would you like me to use on you?” Lisa asked playfully. This time there was no mistaking the look of lust on Lisa’s face. This gave Hank’s dick a big rush.
“This one,” said Hank, holding up the eight-inch purple dong.
Lisa smiled at his choice. It was then that Hank noticed that they weren’t headed for the ballpark.
“I know a nice secluded spot were we can have some fun.” Lisa said. Hank found his heart racing as he realized that his biggest fantasy was going to come true.
When they arrived at the spot, it was a hillside that gave them cover from three sides. They both got in the back seat and started to remove each others clothing. Lisa laid down on top of Hank and probed his mouth with her delicious tongue. While continuing to kiss, Lisa moved her hands down to Hank’s asshole and started to play with it. A jolt of electricity went up Hank’s body and she probed him with her fingers. Soon she had two fingers in him and started to thrust them in and out. Hank was in ecstasy. He played with her nipples with his fingers.
“I think now you’re ready,” Lisa said as reached for the harness. Hank helped her put it on as well as helping with attaching the dildo. “Show me that ass of yours. I think I need to fuck you good.”
Hank got on his hands and knees and showed his ass to her. She put her hands on his hips and placed the tip of the dildo against his bud. Hank quivered in anticipation. She firmly but slowly slipped the dildo into him. The pleasure was almost unbearable for Hank. He wanted her to start thrusting into him and moved his ass closer to her.
“Fuck me,” he pleaded.
“Patience, my sweet, Patience.” She finally slid the length of the dildo inside of him and slowly started to thrust. Hank moved with her tempo.
It was the most amazing feeling for Hank. The slow thrusting made his prostate come alive and his cock felt on fire. Lisa started to quicken her thrusting.
“Now, you can say ‘fuck me, Lisa” she teased and started to move the dildo almost all the way out and then quickly thrust it all the way in. Hank’s ass moved with her quick thrusts.
“Oh god! Fuck me, Lisa. Fuck me. Fuck me.” Hank yelled as his orgasm started to build. It built deep inside where he never felt it start before. Soon it seemed to take over his whole body and he unleashed a torrent of semen. While the waves of climax hit he begged to Lisa to keep fucking him. His begging sent Lisa over the edge and she too was sent into ecstasy.
Lisa kept pounding into Hank until her orgasm began to subside. Finally she stopped. For a few minutes, no sound could be heard but the sound of their heavy breathing. Finally she removed the dildo from Hank’s ass. They embraced and kissed.
Hank looked at Lisa and said, “That was incredible, You definitely know how to use a cock. I certainly do enjoying being fucked.”
Lisa laughed and looked at him, “We have a ballgame to attend. But then we’ll have time on the way back for another pegging.”
Hank couldn’t wait.