Gina exerts her dominance over her brothers and Simon. Everyone has a good time. This story takes place a week before “Good neighbors, good friends.”
I’ve been working out at the base gym for an hour or so and wondering what the hell for. I’m 5’3”, 110 lbs. and I haven’t seen any change to my body at all. Just a lot of sweat and sore muscles. I was just leaving the gym and heading to the dressing room when I ran into Jason, Gina and Thumpy’s brother. Jason came over to me and said,” Man, we gotta talk.” “Ok, shoot”, I said. “Look Simon, I know you are falling for my sister and that’s cool, but there is a side to her you need to be aware of.” “Oh, what’s that?” I said. “She’s our older sister, and a bit of a control freak. No big deal that is until our little get together last week. Something changed in her. Saturday night our parents went to the NCO club and told us they’d be home late and as usual left Gina in charge.”
“The moment the door closed behind them, Gina tells Thumpy and me to go to our room and underdress. We’re like Yeah!, this is great, we race to our bedroom and strip out of our clothes as fast as possible. She comes in wearing her flannel PJs and sits down on the edge of my bed. She then proceeds to tell us, she’s in charge and we are to do as she says and not to worry, “you boys will enjoy it.” Thumpy and I exchanged glances and said, Ok. I was sitting on the bed next to Gina and she told Thumpy to get on the floor and give me a blow job.” “Ok, so far that doesn’t sound too bad”, I said. “Just wait, once Thumpy gets in position, Gina gets up and kneels behind Thumpy and puts one of her fingers in her mouth, pulls it out and spits on Thumpy’s butt. Then she starts pushing that finger into his butt hole! Thumpy’s head popped up and she smacked is butt hard and told him to keep on sucking cause she was going to finger fuck his ass until I cum in his mouth!”, he said. “Oh shit! Did she do that to you too?” “Yep” he said, “It hurt a little when her finger first went in, but she keeps spitting on my butt and her finger so after a while it felt pretty good. I think she was getting ready to add another finger, but Thumpy couldn’t take it anymore and blew his load into my mouth. Gina got up and went to the bathroom to wash her hands, when she came back, she said, “you’ve been good boys and she would let us do this again real soon, I might even let you fuck each other.”
“Holy shit, she said that?”, I said. “Yep, Simon, looks like YOU created a monster when you finger fucked her ass last week!” Jason said with a sneer. I was about to assure Jason, I’d fix it when Gina walked over and asked what we were talking about. Jason said, “Oh, nothing” and turned and walked off. Gina was really looking good in her workout clothes, 5’6”, 120 lbs. nice tits and a great ass. Gina looked and me and put her arm around my neck and pulled me in closer, “We’re coming to your house today and I’ve got a little surprise for you.” She was smiling when she said it, but something was different. “We’ll see you in about an hour, so get a move on Simon.” She said. I hurried into the dressing room to change and get home, guess I’ll find out what I helped create shortly.
When I got home, I headed to my room and policed it for the afternoons event. Not really sure what Gina has in store for me, but it should be interesting! Jason and Thumpy showed up about 15 minutes later and said Gina would be coming along in a few minutes and that we were to be undressed and be ready to take orders. “Take orders?”, I said. Thumpy piped up and said, “Yeah, she’s really getting off on bossing us around, but it’s been fun, you’ll see.” We proceed to undress and await Gina’s arrival. I asked Thumpy, “How’d you like Gina finger fucking your butt?” He just smiled, and Jason cracked up.
Gina made her grand entrance; she had changed clothes to a crop top and a really short denim mini skirt with white knee-high boots. (it was the late sixties after all) As I mention before Gina is taller than us guys, she’s probably 5’6”, those boots put her at 5’9”. She was really towering over us. She ordered us to attention, we’re military brats, so we snapped to. She then walked in front of us, reaching out and feeling each of our quickly inflating dicks. Then she moved behind us, and order us to bend over, and touch the ground with our hands, we complied. I felt one of her hands rub one ass cheek then the other, then she slapped one cheek then the other. She let out a little laugh, “Simon, I love how your skin turns so pink where I smacked your butt.” Next, I felt her hand go between the cheeks and I felt this cold gooey stuff right on my butt hole. Then she moved on to Jason and Thumpy giving each the same treatment.
“Attention Boys!” she snapped. We all popped back up to attention. “Good boys, I have just applied a little lubricate to your butt holes, that should make your next task much more pleasurable. Jason get on the bed with your butt hanging off the edge, pull your legs up to your chest, DO IT NOW!”, she barked. Jason scrambled to get into position. Gina walked over to Jason and took one finger and swirled it around the goo on his butt hole, then she pressed that finger into his butt. Jason let out a little grunt but other than that he seemed to like the sensation. Gina pulled her finger out and order Thumpy to take over finger fucking Jason, except “Use two fingers” she said. Thumpy complied with her orders.
Gina then walked over to me. She bent down slightly and planted a kiss on my lips which I eagerly accepted, when she broke the kiss, she said, “I enjoyed playing with you last week but today’s going to be a bit different, but I think you will enjoy being my sex toy.” “Now, get on the bed beside Thumpy in the same position, I’m gonna make you beg me to cum.” She said with a wicked grin. I hustled over to the bed and got into position with my knees up to my chest and my butt fully exposed to Gina’s intentions.
Gina looked over to Thumpy and said, “go slow, take your time to warm Jason’s butt up, cause in a couple of minutes you’re going to fuck that butt!” The smile on Thumpy’s face was priceless, Jason on the other hand looked a little concerned. Gina then turned her attention back to me. She swirled that finger around my anus gathering all the goo into the center which she then pushed her finger and the goo in. Owww, that burned a little. She heard my moan and grinned broadly, “Yes, Simon, your ass is mine now.” She gave me a moment to adjust to the intrusion then began sawing her finger in and out. She was right it did feel good. This went on for 30 seconds or so then she added another finger. Shit, that burning sensation is back, but she waits until I adjust, then starts sawing again. I noticed, I began to push back against her fingers. That’s what she must have been waiting for because she stops and tells Jason to stop.
“Ok, Thumpy, it’s time to fuck our brother, Jason you be a good boy and ask Thumpy to fuck you.” There was a pause, I didn’t think Jason would do it but then, “Little brother, will you fuck me?” he said. Thumpy replied with a “Oh hell yes, bro! I’ll fuck you senseless!” And with that he moved into position and I watched him line up his 5” dick with Jason’s little brown ass hole. He pressed forward and buried it into his brother. Jason started crawling on his back to move more to the center of the bed and Thumpy climbed onto the bed and nailed him missionary style. It was awesome to watch. Gina drove 3 fingers into me to get my attention.
“Now that you’re warmed up Simon, I’ve got something special for you.”, she said. That’s when she pulled out a hairbrush that had a tapered handle about 6” long and a 1” or so in width. She wiped her fingers on the handle to lube it up and then pushed it slowing into my greedy ass hole. She was very gentle; she’d push in an inch then wait till my breathing slowed back down then add another inch until I felt the bristles touch my butt cheeks. Gina said, “Hold it in Simon, don’t let it drop if you know what’s good for you.” I clamped down hard on the hairbrush. Gina moved up onto the bed and leaned over to give me a very passionate kiss. She leaned back and said, “I’m so proud of you Simon, Jason tried the hairbrush but he begged me to stop after 2”. You swallowed the whole thing! I can’t wait to start getting it moving in you.”
She leaned in to kiss me again while also reaching down and pressed the hairbrush home, then she began sawing it in and out. It was really starting to generate wild sensations within my body. I noticed; I began swiveling my hips to match Gina’s thrusts. She broke the kiss and drove the brush home again. She said, “Simon, check out the boys.”
I turned my head and Jason’s legs were no longer up by his chest. Now, they were wrapped around Thumpy’s hips, like he was trying to pull Thumpy’s dick in deeper. God, they looked so hot! Thumpy was just hammering Jason. To my eye, it looked like Jason was disconnected from it. How could that be, I wondered. Thumpy let out a low moan and jerked real hard a couple times then came to a complete stop. “He’s cumming” Gina said. Can you feel it inside you Jason? “No, but I can feel Thumpy’s dick jerking inside me.” He said. Thumpy said, “God that felt so good, blow jobs are great but a nice tight ass is so much better!” Thumpy began pulling out and Gina yelled, “Stop, let us get closer and watch.” Thumpy pushed back home. Gina pulled the brush from my ass and we both got up and move to either side of Thumpy. “Ok, Thumpy”, he pulled out and stood up, Gina pushed Jason’s legs back up to his chest and we watched Thumpy’s cum drip out of Jason’s ass. Gina told Jason to push and a pretty large gob of semen ran down his ass cheeks.
Gina told Thump and Jason to go clean up but instructed Thumpy not to wipe his butt because Jason will be pounding his ass as soon as they return to the bedroom. Gina turned to me and said “that was so hot, I loved the way the cum dripped out of his ass. Speaking of which, get your butt on the bed and let me finish pounding your ass.” “Yes Mam!” I said. I crawled back onto the bed and Gina told me to lay on my side with my top leg raised. Gina slid in beside me, feet first, and I for the first time saw she wasn’t wearing any underwear. Her pussy had a beautiful moist sheen to it. She didn’t have to command me to eat it! I was on it as soon as it was close enough to taste. Gina slid the brush back into my ass and began sawing it back and forth, my mind was going into overload! Then she popped all my fuses by wrapping her lips around my little stiffy! I licked up and down her slit a few times then brought my hand up and slipped a finger into her pussy, and another into her pre-lubed ass. Seems Gina thought of everything. We were getting into a pretty good rhythm when the boys came back in.
Thump said, “That’s what I want next time, getting fucked by you or Simon and then having someone else giving me a blow job at the same time!” Jason laughed and said, “You’re getting to be a greedy little bastard aren’t ya.!” Then Jason said, “you know what might ever be better, how about you and Simon each giving the other a blow job and I’m fucking your ass at the same time!” I hesitantly removed my lips from Gina’s tasty pussy and said, “you know, laying on our sides like Gina and I are now, it would be possible to have another partner or two fuck some ass of the blow job boys.” I went back to pleasuring Gina, but I could hear the gears turning in everyone’s head.
Gina piped up, “Enough talk, Thumpy grab one of those pillows then lay on your stomach, put the pillow under your hips to raise your ass up. Jason’s going to pound your ass. Once Thumpy was in position, Jason climbed up between his legs and lined up his “monster 6” dick”. Thumpy called back to him, “Oh please big brother don’t hurt me with that thing!” Once the laughter died down, Jason without warning drove his cock straight into Thumpy’s ass. And held on tight, as Thumpy started bucking. What a sight! Jason rode his ass! Once Thumpy settled down, Jason went to town with a big grin on his face! It seemed to me Jason was kinda mean to Thump, he didn’t warm his ass up at all, just slammed into his baby brother, and really seemed to enjoy Thumpy’s thrashing about. ???
I was barely hanging on to my sanity, the sensory overload was becoming almost painful. The nerve endings in my butt were causing my legs to shake like they were made of jelly. Gina’s oral menstruations on my cock felt like she was going to milk the life out of me. Then throw in the desire to make her come on my face with two fingers plunging into her pussy and ass became too much. I felt myself letting go, I love cumming in Gina’s mouth, that girl can suck! About the same time her legs closed around my head, and I knew she was cumming also. Fucking perfect! Her pussy and ass really put the squeeze on my fingers.
Gina finally released my head, and we just laid there, hairbrush buried to the bristles in my ass, and my fingers a deep as they would go in Gina’s ass and pussy. I reluctantly removed my fingers and Gina pulled the brush out. God, I feel so empty! I tell Gina about it and she reverses position and grabs my head in her hands and tells me, “Don’t worry Simon, I can promise you, I’ll keep your greedy hole happy, and speaking of greedy holes, I’ve saved my ass for you, when you’re ready to fuck it.” I looked down at my cock and it was already springing to life at the mere thought of fucking Gina.
I rolled over on top of Gina and gave her my best passionate kiss, she hugged me tight. I couldn’t possibly imagine anything feeling better than this. Boy, was I wrong. Gina reminded me, “You can fuck my ass but not my pussy. I don’t want to get pregnant.” I lifted myself up off Gina’s body and she grabbed a pillow which she slid under her hips. Then she pulled her legs up to her chest, presenting me with total access to both her pussy and ass. God, I love looking at Gina’s pink pussy, but today’s target is her sweet ass hole. I look over and Jason is still wailing on Thumpy’s ass and now it’s my turn. Fucking my first girl. I moved into position and realized I can’t see my target, so I gripped my dick with my hand and moved in closer. I started moving my cock up and down trying to find the right spot, suddenly my cock found itself in a nice warm wet spot, I was ready to drive it home when Gina’s hand pushed me off and she said, “Lower Simon, no pussy for you!” “My dick doesn’t have eyes, help guide me in! I said.
Gina’s hand grabbed my dick, and she guided me in. “Now, go slow Simon, you’ve loosened me up with your fingers but, it’s still tight.” “Yes, Love”, I said. It was amazing as I pressed my cock into her ass how there was this resistance keeping me out until I pushed past this point then suddenly my cock head was in her! I stopped, dead in my tracks, I could see Gina is biting her lip. I waited until she nodded to go deeper. I feed her my cock inch by inch, thank God Gina had the foresight to have lubed her butt. It felt so good, every now and then I could feel Gina squeeze down on my cock. She keeps that up I’ll cum without finishing my first stroke. Once I was all in, I began a slow withdrawal of my cock, damn near pulled it all the way out! I stopped with just the head still in her, then slowly pushed it all the way back in. I leaned down and kissed Gina again, this was just so wonderful. She looked up at me and smiled and said, “you gave me your ass, it’s only fair that you get mine.” I kissed her again and she began moving her hips in a circular motion, letting my cock explore all of her tight butt.
I glanced over at Thumpy and Jason, Thumpy was just lying there with his mouth half open emitting quiet grunts when Jason would hit bottom. Jason for his part and worked up quite a sweat, hammering his brother’s ass. I began sawing into Gina in earnest, with the pace slowly building to a full-on rut. Jason looked over to me and smiled and said, “I’m cumming, I’m going to fill his butt with my cream!” With that his face contorted into ecstasy and he did his final deep dive into Thumpy.
Meanwhile, I’m shagging Gina’s ass with everything I’ve got. She has dropped her legs down and wrapped around my waist, she’s trying to temper my thrusts by pulling me into her. I think she’s getting off every time my pubs bang into her clit. It finally becomes too much for me and I blast several streams of cum into that luscious ass and collapse on top of her. She takes my face in her hands and kisses me. Looking me straight in the eyes she says, “that was nice, I hope one day soon you can make love to me in my pussy, just like you did to my ass.” I kissed her, then felt my cock slowing being pushed out of her butt. I slipped off her and she pulled her legs back up to her chest and Jason, Thumpy and myself watched as some white Simon cum dripped out of her butt. One of my proudest moments!
I helped Gina off my bed and she headed to the bathroom to clean up. We three boys just stared at each other with shit eating grins. This has been a great day; we each fucked our first ass and we each (sorta) got fucked in the ass. I can’t think of a better day. Gina returned from the bathroom looking marvelous and Jason pulled her aside. They whispered to each other for a bit, then Gina called Thumpy over and they whispered some more. When they finally broke up all three turned to me. Gina apparently was the elected spokesperson. “Simon” she said, “it has been brought to my attention that both Jason and Thumpy have been fucked by a male cock, you kind sir, have not. Therefore, we have decided we need to rectify this situation by having first Thumpy then Jason taking turns in your butt.” “What???” I said. Gina said, “boys let’s get him into position.” Gina climbed back onto the bed and spread her legs showing her freshly tidied up pussy, and the boys led me between her legs, where I was to put my front half on the bed to orally satisfy Gina, while giving the boys access to my ass.
Thumpy slid in behind me and didn’t waste any time, he was all recharged from being fucked by Jason, so he wanted a quick release. He lined up, eased his cock head into my butt hole, gave me a second to breath then pushed it home. Damn that felt good, meanwhile, Gina grabs my head and pushes her glistening pussy into my face. I began licking her to the beat of Thumpy pounding my ass. Gina, ruffled my hair and smiled at me, “Eat it good Simon! or I’ll give the boys the hairbrush.” I didn’t need any more motivation. My ass was sending pleasure signals to my brain. Then I felt Thumpy’s rhythm change, he was going to cum. He did three fast hard jabs then stopped and leaned on my back. I could feel his cock pulsating. Yes, I drained one and have one to go.
The moment Thumpy’s cock slipped out of my butt, Jason was quickly in place to get him some. He slammed it in and rode my ass for a good 5 minutes. He sure knows how to use what he’s got! I continued to eat Gina until I felt myself cumming! Cumming without even touching my dick? It wasn’t a normal cum, a couple squirts and that’s it. No, this was just a steady small stream of cum just leaking out of my cock. I couldn’t help myself, I called to Jason, “Fuck me harder!” Jason doubled his efforts, he was pounding my ass like a jack hammer. My legs were shaking so badly they gave way, and I slid off the bed down to the floor, Jason riding me all the way down. He started cumming when we hit the floor.
As I laid there totally exhausted and quivering like a bowl of jello, Gina got off the bed, Jason and Thumpy stood above me, watching the cum oozing out of my battered hole. “Jesus that was hot” exclaimed Thumpy. All Jason could do between gasps for air is grin. Gina bent down and scooped up some of the boys cum and pushed it back into my ass. I groaned, Gina said, “Simon, I’m impressed, you’re an anal slut, I’m going to have to think about how I can challenge your abilities. I think we’re going to have fun with you, my Love.” All I could do is weakly smile, the boys started cracking up. Jason said, ”Simon, sure glad you like brown dick, cause we’re going to give you a lot of it.”
The brothers went to the bathroom to get cleaned up and dressed to head home. Gina sat down on the floor next to me and stroked my hair. “God that was awesome session!” she said. “I love playing with you Simon, you eat pussy very well, and you followed my lead without complaining about it.” “How did you like getting fucked by my brothers?” “Help me get to the bathroom, Gina.” She stood and gave me a hand to get to my feet on wobbly legs. She followed me into the bathroom where I plopped down on the toilet and let out one long, really long juicy fart. She started laughing.
I looked up at her and said, “Today was an incredible experience. You fucked my ass with a brush handle, it stretched me and hurt a little but then it started feeling really good. Then I got to watch your brothers fuck each other, that was hot. I think Thumpy really enjoyed it, and Jason is a fucking monster. I then had three more firsts, the head of my dick accidently entered your pussy, that was awesome by the way! Then I got to fuck your glorious butt, it was so tight, I loved it. Then there was becoming a pussy for your brothers. You had stretched me out so, I was ready for them physically, but the submitting to another man was a bit of a mind fuck. I think if I didn’t have my face buried in your pussy I would have probably backed out.”
She interrupted me, “What do you mean submitting was a mind fuck?” “Come on Gina, I’m a man and I wasn’t acting very manly. I was just kneeling there letting them do what they wanted and I got off on it! I’m so embarrassed.” Gina looked me straight in the eyes and said, “How did you describe Jason and Thumpy fucking each other?” I paused and said,” it was hot.” “So why are you ashamed of doing the same thing they did?” she asked. Ok, I was stumped for an answer. Then she kissed me and suddenly everything was good again. “Let’s get you and the house cleaned up.