“Hey Dolly. What’s up?”
Dolly was a sexy 18 year old girl that lived on a farm with her dad and 4 brothers. Word around town is she’s waiting for marriage to have sex but you can talk her into a hand job. I’ve been waiting for her to turn legal age so I can test that rumor out, but I’ll have to be careful. Her father and brothers wouldn’t like a 23-year-old messing with her.
“Hello Jack.” Dolly smiled wide. Despite our age difference she knew me well as she was close friends with my best friend’s sister.
“You look sexy today! What would your boyfriend say if he knew you were out in town in that?” She wore some jean cutoffs that were just a bit too short, a thin light blue top, and either a very cheap bra or none at all. And I knew she didn’t have a boyfriend.
“I don’t have no boyfriend.” Dolly shyly responded in small town slang.
“Girl as pretty as you must have boys lined up though.” I schmoozed her. “Where you going anyway? Need a ride?”
“If you could run me home that’d be great. I missed the bus and Jenny had her car taken away.” Jenny was earlier mentioned sister of my best friend.
“Let’s go gorgeous!” I told her and walked toward my truck. Maybe I was just horny at the thought of a hand job, but Dolly looked extra sexy today. Her hair was light brown with a natural red hue to it and sat down on top of what had to be D size titties. I should have let her lead the way so I could check out her ass cheeks hanging out of those shorts.
20 mins later and a lot of small talk and compliments we arrived at Dolly’s family farm. Her mother had died years earlier from cancer, so she was left with the womanly duties around the farm.
“Where is your dad and brothers?” I asked.
“Daddy took the boys over to Potterville to look at some equipment. They’ll be along later.” Dolly said as she hopped out of my truck.
“How about some lemonade or a water for a thirsty guy?” I asked exiting the truck and following her towards the house.
“Sure. But real quick. I got stuff to do before the boys get home.” Dolly said.
“Dolly I’d sure like to kiss you.” I said walking closer to her in the kitchen a few minutes later.
“Gee I don’t know.” Her face turned red and she looked to the floor.
I decided to make a move and put my hand under her chin and lifted it so she was looking at me. I leaned forward and kissed her gently on the lips. She didn’t shy away or resist, so I kissed her again a little more passionately. So far so good.
“I have chores to do Jack.” Dolly said pulling away.
“Just a few more kissed Dolly. You kiss so good.” Truthfully, I was doing all the kissing and she was just passively receiving my advances.
I leaned in and we kissed some more. My cock grew very stiff in my jeans. I decided to play to the rumors and take my shot. While we kissed I reached down with one hand and undid my jeans and allowed my swollen dick to pop through the flap in my boxers.
I broke our kiss and said, “Dolly look what you’ve done to me!” And pointed my eyes down. She followed my eyes and looked down to my cock jutting out of my jeans.
“Jack! Oh my gosh!” She took half a step back as if she’d seen a spider. “Put that away!”
“Dolly I can’t when it’s so swollen. Can’t you help me out so I can get it back to regular size?” My dick wasn’t porno sized, but I was above average at 7″ and had pretty good thickness. Plenty of women had told me I had an artist for a doctor because my circumcision was flawless.
Dolly looked at my dick for what seemed like 5 minutes but was probably 5 seconds and then reached out to touch it.
“If I do this you need to hurry up and finish and get going so I can get my chores done.” She told me.
“Of course Dolly!” Like most guys I would’ve agreed to anything that would get her to pumping on my dick.
Dolly began sliding her hand on the shaft of my dick. It appeared she was sizing me up, maybe comparing me to the others she’s jerked on. I gave her some words of affirmation to let her know I was enjoying her touch.
“That’s feels nice Dolly. You got me so excited!” I put it all on her. “Only right that you help me out with this.”
“Just hurry up Jack.” Dolly said stroking my cock almost like she milks her daddy’s cows.
“I’m trying but it’s just not right yet. Can you twist your hand a bit? Maybe change angles.” If I’m being honest this wasn’t a good hand job at all. I was trying to concentrate on her big tits but her rhythm was distracting me. Hand manipulation is a lost art for sure.
“How about we just have sex Dolly?” Figured I throw that out there. I mean, I didn’t know for sure she was waiting for marriage. “That will only take a minute for sure!” I guaranteed her.
“I don’t do that until I’m married Jack.” She confirmed the chatter and continued her weird hand cadence in my meat.
“How about on the backside Dolly? You’ll still be a virgin.” I’m was really reaching now.
“What?! That’s just wrong.” Dolly stopped pumping her hand and turned away.
I came up behind her and pushed my hard dick into the middle of her shorts and reached around and pulled her into me while both my hands covered her tits. Admittedly I got a little too aggressive.
Dolly tried to pull away but by doing that she pushed her ass into my crotch even more. I adjusted myself so my dong was now poking through her legs right up against her vagina still covered in panties and shorts.
“I need some relief Dolly. You owe this to me!” I’m ashamed to admit I lost my mind a little and got even more aggressive. I wanted to fuck her so bad at this point and my cock was doing the decision making. I held her with one arm and pushed her shorts and panties down with the other hand. My dick was now laying between her legs up against her moist lips.
“Jack stop it! Please. I don’t want to have sex.” Dolly struggled but it was clear I was stronger and wanted to have my way. “You can do my butt. Just please, I’m a virgin.” She was almost in tears now.
Did I feel bad? Yes. Did I plan to continue this and fuck her ass? Yes.
I loosened my hold on her a little and pulled my dick back slowly to get as much of her wetness on me as possible to make entering her ass easier.
I put the head of my dick on her ass sphincter and gyrated my hips a little to allow her to prepare for entry. “It may hurt for a few minutes but you’ll like it after that!” I told her as I pushed my hips into her attempting to breach her asshole.
“What the fuck is going on here?” A mean male voice said from behind me.
I pulled back and let go of Dolly. She fell to the floor with her shorts and panties still at her ankles. I turned to see who was home with my cock still pointing straight out of my pants.
“Someone better start talking soon!” Dolly’s father said.
“Daddy I’m still a virgin. I told him I wanted to wait. We kissed but that’s all. Jack had a swollen penis and was making me do butt sex. That’s all daddy!” Dolly spilled her guts.
“Oh, is that right? Making you do butt sex?” He questioned. “Dolly get your clothes on and go about your chores. I’ll take care of Mr. Jack.”
I reached to tuck my now softening dick back into my jeans but was interrupted.
“Don’t put that away because of me.” Dolly’s dad said sarcastically. “Need some relief still don’t ya?” As he said that three of his sons came into the kitchen.
Sam was my age, Richard was 21, and Josiah was 19. “What’s going on dad?” The asked in unison seeing me with my prick out.
“This boy wanted to force Dolly to have butt sex.” He told the pack.
“It wasn’t exactly like…”
“Shut up Jack!” Sam spoke up. “You wanna force my sister to…” he was angry and couldn’t finish his thought.
“Well boys I think Mr. Jack here needs some relief. And since he likes butt sex so much let’s help him out.” Dad smirked.
Are they going to make me fuck a chicken in the ass? A pig? What’s their plan?
“Drop your pants boys, we’re fixin’ to fuck Mr. Jack in his ass.” Dad instructed the boys as his pants opened to reveal a short crooked dick.
Before I knew what had happened, I was surrounded by the brothers and pushed to an island counter. One went around and held my wrists from the other side keeping me bent over the front side. Next thing I know Dolly’s dad is pushing his short dry dick into my asshole. It hurt like hell.
“Just a little butt sex Mr. Jack.” Her father laughed along with his sons. “He’s kinda dry now but I’ll get him ready for you boys.”
After several minutes of fucking and hollering Dolly’s dad shot a load into my ass. His short dick didn’t place it very deep and I could feel most of it leaking from my ass. Sam stepped up and using his father’s semen he pushed his longer thicker cock into my ass.
Sam pumped my ass for about 3 or 4 minutes before he buried a load deep in my bowels. Josiah was next as Richard was still holding my wrists. Josiah seemed to be long but thin. His dick fell right in but hit a spot very deep inside me. I wondered if there was enough friction to make him cum. Didn’t take long to find out as he too was leaving a hot load deep inside me.
Richard told Sam to hold so he could come around and take his shot.
“You’re in for it now Mr. Jack!” Dad laughed. “Richard goes last because he’s the biggest!”
Richard pushed his thick cock into my now used asshole, but it was still a very tight fit. I could feel places inside me being stimulated that had not been touched by any of the others. At this point I wasn’t in pain but I can’t tell you I was having a good time either. The motion on my prostate had gotten me hard and was pushing pre-cum out the tip of my dick.
“You wanted butt sex you got it!” Richard yelled to high fives from his family. “Here’s another hot deposit!” He announced as he added his seed to my ass.
“Don’t ever come around my daughter again.” Dolly’s father said as he smacked my bare ass. I felt hollowed out while I laid over the counter.
I turned around to the boys and their dad composing themselves and buttoning up their pants. I reached down and pulled my pants up and slowly walked out of the house. As I got on the porch I heard a quiet voice to my left call my name.
I turned to see Dolly shucking some ears of corn and throwing them into a bucket of water. “Sorry Jack. But you should know, you’re not the first one to get caught with me and get that treatment.”
Funny how that rumor never got around. Much like I plan to though, I guess the other guys kept that part a secret.