Neighbors in a culdesac seem like the best people to get advice from. But they may not be the most likely confidants.
Culdesac Hers
In a small urban town just north of LA where the people fit loosely around church nor state lived a young woman coming of age in this world of information. She wanted guidance, support and inspiration. Her parents raised her by one motto: 'Plain girls that want to be included in sports can't be shy. Be Courageous.' This taught her two things; 1. Don't be plain, and 2. Just go for it. Coming of age in the modern age was tough, fraught with too many choices and not enough boundary to be certain.
Her family lived at the start of a culdesac, a dead end street punctuated by a circle. They enjoyed a close knit neighborhood. Everybody got included in each gathering be it religion, sport, or season. So, folks were familiar with each other and generally accepting. Even the gay couple at the culdesac. In some cases especially them as we're about to find out.
Sally turned 18 last year just before graduation and more importantly, just before Summer. Why Summer? Sally was a cute, blond haired young woman. With overprotective parents that only recently allowed her to wear skimpy outfits and risque bikinis. On her eighteenth birthday she secretly shaved her pubic hairs as smooth as her belly. She also bought a string bikini with a thong bottom. She wanted attention from her boyfriend, also a new experience for her.
Her parents did their best to accept her quirky character and brash boldness but neither of them could bring themselves to coach her on boys, boundaries and most of all sex. All they could do was keep close tabs on her and gently urge her to be safe, be smart, and don't get pregnant. The last thing was repeated ad nauseam. Sally was determined to honor that request. Her boyfriend on the other hand was mischievous and daring. Something that attracted her to him. She dressed for him.
Since coming of age at 16 her life has changed dramatically. During the first Summer of her coming of age, she kissed and cuddled her boyfriend, Billy. They became exclusive by the end of Summer, even tho her parent were very restrictive. Two years passed and they are still together. They have gotten closer and experimented with touching rubbing and kissing. Eventually giving him a blowjob while he licked her little pussy. But, by the end of Summer Billy wanted more. She was steadfast and wouldn't allow it reminding him that she wasn't going to get pregnant. He said he was willing to try other things and was saying things like: 'I'd love to fuck your sweet ass' and 'make you cum on my dick' among others. It made Sally feel excited. She was torn. When Fall semester started, Billy went away to college while Sally stayed home to work.
She received letters and phone calls from Billy who insisted that he was saving himself for her. They saw each other over Christmas break and they were inseparable. Sally was happy and wanted to show Billy how much she wanted him but wasn't sure what was safe. He went back to school before she could find a solution. When Spring was coming to an end Sally knew she needed to do something before Billy came home from college. Something she knew he wanted and something she wanted but didn't know how.
George and Stan lived at the end of the culdesac. They were great fun and always joined in every celebration. Their yard was immaculate and their tastes were top notch. No one seemed to mind that they were two men living together. They were generous, happy, caring people. Sally's family knew them well enough and Sally felt they were very trustworthy. She wasn't able to speak to her parents about some things so she decided to ask their advice.
Sunday afternoon Stan heard a knock at the door. When he opened it he saw Sally dressed in her summer clothes; matching top and shorts, thin, light weight, skin tight which accentuated the string bikini top and thong bottoms underneath. She was a strong willed girl and Stan knew her on sight but played coy, “Won't you come in... Sally. Right?” Sally nodded and boldly went inside where she was offered a soda and a seat. Stan wasn't surprised by her attire. He'd watched her grow up and change styles along the way. This one was a particularly enjoyable one. “What can we do for you?”
Sally wasn't shy around them having seen them being intimate around the pool and social gatherings. Still it was not the normal thing you talk to your neighbors about. “It feels a little awkward...” she started, then crossed her legs and arched her back. “Wait. This is about your boyfriend. Isn't it?” Sally's eyes brightened and she shook her head. “The guy in the Camaro...” “Yes. Billy.” Stan walked to the kitchen and made himself a drink. Sally continued, “He's nice. I like him.” Stan took a sip, “And you don't want to lose him. Am I right?”
Sally shook her head again fidgeting in her seat. She felt embarrassed more than shy. Stan looked her over, “Have you given him a blowjob yet?” Sally blushed and looked around, “Yes.” His voice was confident, commanding and she found it disarming. Stan smiled, “Has he licked your pussy?” Sally fidgeted in her seat, “Yes.” Stan looked down at his drink, “Have you had intercourse.” “NO! I don't want to get pregnant.” “No, of course not.” Stan finished his drink and paused to let Sally form her own questions. “Well?”
Sally began a long monologue about their passionate moments and her feelings and about some of the things Billy had said to her. Lastly about things he did to her. Apparently the last time they were intimate together, while Billy was licking her to orgasm he slid a finger into her ass. Sally told him it was disgusting but in reality it was the thing that made her cum, hard. His tongue was good and she really liked him eating her out, but.
“But?” Stan said leaning forward to hear her every word. “I want to learn about anal sex.” Stan smiled and leaned back a little, “That's not going to keep him happy.” Sally sunk down in her chair. Her idea was squashed. Then Stan stood up, “You need to sell him on your love. You want him to feel like you're the best thing he could ever want.” Sally looked encouraged but still uncertain. Stan just stood there looking at her. Sally looked at him waiting, eager for his guidance.
Stan was bisexual and wanted to teach Sally things. Now he had an opportunity, “If you want our help you'll need to do whatever we say. And you can't be shy.” Sally stood up, chest out and smiled, “I'm not shy!” He was counting on it, “Good. Now, show me how you give a blowjob.” Sally's mouth dropped open, “What? Here? Now?” Stan shook his head, “If you want our help you can't be shy.” Sally took a step then hesitated. She wanted to say something. But what? Stan called out for his boyfriend, “George! Give me a blowjob.” George's head appeared from around a corner, “Really?”
George rushed into the room glancing at Sally and kissed Stan on the lips while he slid his hand down Stan's pants. In a matter of seconds George was eagerly licking and sucking a big dick. Sally watched as Stan's dick grew stiff and long under George's skilled care. Sally could feel herself flush. Stan looked at Sally, “See how eager George is? Doesn't it look like he really wants me to be happy?” Then he called George off. George reluctantly relinquished Stan's stiff member. It just stuck out there in the open. Stan turned back to Sally, “Now you try.” Sally looked puzzled for a moment, “Shouldn't we start with kissing.”
Stan shook his head, tsk, tsk, tsk, “George! Make-out session.” George popped around the corner again and Stan pointed to Sally. He came over to Sally and planted a big wet one right on her lips. It took a moment for Sally to get over the shock. She could tell his lips were slick and hot having just been sucking on Stan's dick. Then George slid his tongue into her mouth and she melted. Her eyes closed and started kissing him back. A couple minutes later she was eager and tingling. George slid his hands over he supple body and Sally's breath became hot and labored. He tweaked her nipples and ran one hand up her back. George's hand ran through her hair and he pulled her away from the kiss.
Sally was weak and docile, her head floated on her shoulders. Her eyes were closed and her mouth slack. George's hand urged her head forward and she prepared for another kiss. Suddenly she felt something bigger than a tongue push into her mouth. It was very big, stretching her mouth wide. She recognized the shape and closed her lips around it. She heard Stan's sonorous voice, “Now it's your turn. Show me how you give a blowjob. Pretend I'm Billy” Sally sucked it in as it stretched her mouth wider. It felt so strong, warm and smooth. It felt good in her mouth. Like Billy's did.
Sally suddenly stopped herself and pulled off. Looking up at Stan she gasped to catch her breath, “No. This is cheating. I don't want to cheat on Billy.” Stan shook his head, “We can stop if you've had enough.” He watched the look in her eyes carefully, “You asked for our help. We're teaching you what you wanted. That's not cheating.” Sally was panting as she licked her lips. “But we can stop if you want to.” Stan pushed his big dick against her lips. Sally took a deep breath, “Well, OK. As long as you don't cum in my mouth.” Then she opened her mouth as wide as she could and enveloped the head in her warm, moist mouth again.
As Sally began to get into sucking Stan's dick he said, “Are you able to put all of Billy's dick into your mouth?” She coughed around his dick and shook her head 'No.' “You need to practice getting all of it in. That's the way guys like it.” Then he push a little and Sally let it touch the back of her throat. She swallowed hard but kept sucking. It felt good. Tasted good. She tried again and again. His big dick bounced off the back of her throat a couple times before she slid back a little to catch her breath. She rested and just sucked on the head like Billy wants her to do it. That she knows how to do.
“Do you let Billy cum in your mouth?” She shook her head 'No' without removing his dick from her mouth. “If you want Billy to really like you, you need to let him cum in you mouth.” Sally made a gurgling sound but kept sucking. She pushed it to the back of her mouth again. But it wouldn't go any further. “And you need to learn to swallow it.” Sally pulled off the slick, dripping shaft and stared at it, “I can't. I don't want to get pregnant!” She couldn't take her eyes off his big dick. This was the first time she had a good look at it.
It was bigger than Billy's, obviously. The head had a flared ridge around the head like a dinosaur's crest. She felt it rubbing against the roof of her mouth. It was smooth and shiny and it pulsed. She rubbed it with her hand and she could feel how strong it was. Then she remembered all Stan was saying. It made her weak to think about it. “You need to keep practicing. Try to get more in your mouth.” Sally closed her eyes and opened her mouth. Then she pulled his dick to her mouth and started sucking again. “And don't worry. You're not going to get pregnant by swallowing cum. It's impossible.”
“But I won't cum in your mouth unless you ask for it.” Stan put his hand on the back of her head and pushed his dick as far as it would go. Sally wiggled her head and gurgled but she kept trying. She wanted to be able to do it. After a minute she was breathing heavy and still only sucking a small amount of his big shaft. Stan was enjoying it nonetheless. “Good. Now stand up so I can check out your bottom.” Sally reluctantly slid off his dick and stood up, leaned her body against his and planted a kiss on his lips. Stan kissed her back, “That's nice. But, I didn't mean stop sucking.” He kissed her again, “Just bend over and keep practicing.”
Sally was breathless. Her brain was foggy. The more she sucked, the more she liked it. The more it turned her on. She was glad to keep trying. As she bent over Stan found the back of her thong that was sticking out from the top of her tight shorts. Then when Sally slid down on his shaft, he pulled up on her thong string. Her hips wiggled and she slurped loudly. When he did it again Sally bounced his dick against the back of her mouth and sucked. Stan smiled to himself. This was going to be fun. He started to slide his hand down her shorts when Sally quickly reached up and slid them off her little bottom to hang snuggly around the top of her legs. Her butt bounced with bold excitement.
Stan put his hand on her bottom and his fingers touched he hot, wet pussy lips. He rubbed her juices around then stuck a finger into her pussy. Sally groaned, she shook and sucked harder. Then Stan spread her slippery juices around her tight little butt hole. Her hips jumped and wiggled against his efforts. She pulled off his dick, “Be gentle.” Then she returned to sucking without waiting for a reply. Stan waited until she had his dick all the way to the back of her throat and he shoved a finger all the way in to her tight little hole.
“Did you tell Billy to be gentle?” he held it all the way in and wiggled it around before pulling it out. Sally's nubile body shook and she groaned. “I'll bet he just did it and you liked it.” Stan shoved his finger all the way back in again, “Beside, you're so tight we're going to have to work on that too. You won't be able to take Billy's dick without some practice.” Sally was sucking hard again and the head of Stan's dick was verging on entering her throat. Stan noticed his dirty words were helping. But her mouth and jaw were too tight. Stan took the obvious route.
“Maybe you should practice with mine first.” Sally couldn't believe what she had just heard and her jaw unhinged. With that the big head of Stan's dick popped into her throat for the first time. Her body jerked back but Stan push his hand against her butt holding her from escaping. She froze for a moment. Stan wiggled his hand on her bottom and the finger in her butt. She couldn't swallow, she couldn't pull away. The more she relaxed the more she didn't want to. Stan started pumping his finger hard in her ass and Sally felt his dick inch into her throat. It was so deep. Her head was swimming. How did she get here? What was she thinking? She came here for advice. Now she's sucking cock and getting finger fucked in the ass. It was so sudden. So daring. Her body was buzzing and she felt tingling all over.
“See there. You just need a little practice. You're almost halfway down my dick.” Sally didn't care about it at that moment. She was overwhelmed with excitement. She was too busy telling herself, 'Don't cum. Don't cum. Don't cum.' She wasn't sure about having an orgasm with someone other than Billy. Stan's hand kept pumping against her body, spanking her bottom, and that pushed his dick deeper and deeper. 'Do not cum. Do not cum. Do... not...' Suddenly her body stiffened and shook. She was fighting hard to keep it in and focusing all her energy on sucking. Then she felt pubic hairs against her nose, and she could no longer hold back.
Stan could tell what was happening and he cradled her head sliding his dick all the way in and out with her convulsions, “Good job. You were able to get a dick all in on your first practice and you apparently enjoyed it.” He slowed down and let her finish her orgasm. Her legs were shaking as she let his dick slide out of her mouth. She was gasping and whining through the waves of pleasure. Stan pumped his finger in time with her orgasm until she pushed back and humped his finger. Her head turned up to look into Stan's eyes. Her face slack, her pupils wide.
Stan pulled out his finger and spanked her bottom, “Ok. That was a good first try. But you'll need practice. I've got some homework for you. Then we'll meet midweek to see how you're progressing.” With that he pulled up her thong and shorts and guided her back to her chair. She was dazed and still high from her orgasm. He left the room for a little while leaving Sally alone to think about what had just happened. Her head was spinning. Her heart was pounding. And her body wanted more. It made her wondered what her homework would be.
When Stan returned he had a small bag with a butt plug and lubricant, “Put this in your butt each day for ten minutes or so. Longer if you are comfortable with it. Then on Wednesday, put it in and walk down here for your next lesson.” Sally was still dazed and looked up at Stan with the butt plug in his hand. “Once its under your clothes, no one will know its there. You could even where it around your house. If you want.” Sally's eyes opened wide. It transfixed her to imagine what it would be like.
“Here. Let's try it now.” Sally stood up her head turned for the door but her body wouldn't move. Her groin was throbbing as she visualized what she was supposed to do. He bent her over and she pulled her shorts and thong over her round butt by herself again. She watched as if from outside herself as Stan demonstrated, “First you put a little lube on your bottom, then some on the plug.” Sally sighed as the plug pushed against her tight hole. “Then slide it in and out a couple times.” She could feel it stretching her tender butt. It slid in and out smoothly. Gently. Sally closed her eyes as the sensations filled her body and mind. She tried not to think about it being someone's dick. Until.
“Then you push it all the way in.” It started to hurt as it stretched her further until it popped in. She stood up and shook, “Ooh!” Sally tightened her cheeks. Stan wiggled it around making sure it was in all the way then pulled up her thong and shorts, “See there. You can't even tell its in. Go ahead and walk around.” She took a couple steps before stopping and shaking again. Then she walked back to Stan with a waddle. Then putting her hand on her bottom she felt around. When she brushed past it her butt twitched. She could barely feel it but she knew it was there.
Stan saw her face when she touched it. “Maybe you should just wear it home.” he spanked her right on the butt and handed her the bag with the lube and walked her to the door. She tried not to waddle and did her best to act nonchalant. “Remember, once a day for at least ten minutes. Then Wednesday wear it and come here for your next lesson. Got it?” Sally shook her head yes. A smile plastered on her face. She was still in a daze. That was one of the best orgasms she had ever had. Stan's voice echoed, “4 o'clock.” Her mind couldn't focus but her body would remember, 'Wednesday 4pm – wear it here.'
During the next couple days she did as she was told and found that it got easier to put in and walk around. It also got her excited more easily and she masturbated with it in imagining Billy giving it to her. On Wednesday she dressed for Billy and headed for Stan and George's eager for her next lesson. She knocked on their door promptly at 4 and when Stan opened the door he was surprised to see her eager and confident. She was dressed to kill and Stan suspected she was wearing what she would wear to date Billy. Lucky guy. Sally was wearing a cut-off Tee with a short skirt, all in white and sandals. Her nipples were hard proving two things, 1. she wasn't wearing a bra, 2. she enjoyed her homework. He invited her in.
Stan closed the door behind her. “Ok. So, imagine you are seeing Billy for the first time in a while. How would you greet him?” Sally walked right up to Stan with bold confidence, rubbed her body against him and gave him a big kiss. She slid her tongue into his mouth and her hand up his leg. She could feel his big dick already starting to swell. “I've missed you. I want to show you how much I missed you. Can I suck your dick?” Sally opened Stan's pants eagerly without waiting for his answer. She nervously fumble with the belt and zipper until her treasure appeared from hiding. She went back to kissing him on the lips as she began stroking his big dick.
Stan slid his hands under her dress and found bare cheeks split by a laced thong. Underneath that was the inserted plug. He returned her kiss while he pressed against the butt plug. Sally went up on her toes and moaned into Stan's mouth. “Seems like you enjoyed your homework.” She pulled back and looked up into his eyes. She was searching for something. Then she bent over leaving her ass exposed as Stan had instructed her before and licked and kissed his stiffening member. Sally had been waiting for this since she left the other day and was so excited she tried to swallow his dick on the first try. She gagged herself but wouldn't be deterred. She tried and tried. Stan knew what would probably help.
As Sally pushed herself down on his long shaft, Stan wiggled the butt plug around then spanked it gently over and over. Her young body responded perfectly. But she still wasn't able to swallow it. Stan pushed hard against the plug, “Are you ready for your next lesson?” Sally was imagining what would happen next. Her mind remembered their first lesson when Stan said she would have to be able to take his big dick in her ass. Her eyes rolled back and her jaw dropped. With that Stan's dick slid past her tight throat again. Her body shook with the thought and the realization that his dick was down her throat. For the second time. She slid herself past the halfway point and bobbed up and down with delight.
“I think you're ready. Let's head to the bedroom.” Sally pulled off his dick reluctantly. Her mind was stuck on something as Stan urged her out of the living room. Stan kept his hand on the plug as he guided her hesitantly to the bedroom. “Are you sure this isn't cheating?” Stan wiggled the butt plug, “No. It's just practice. But we can stop if you don't want any more.” Sally's mind was still uncertain but her body didn't want it to stop. The sensations her body was feeling left her wanting more. The thought of Stan's big dick in her mouth just minutes ago made her swallow hard, “Maybe just a little more. For practice.”
When they got to the bedroom Stan pulled her in and kissed her deeply. He shook her bare ass cheeks and roughly squeezed them. Then he pulled her away and pointed to the bed, “Take your clothes off and get on the bed.” She slipped out of her clothes cautiously and sat on the edge. Stan looked back into her stare, “So to start with, do you want to show me how you put the plug in by yourself?” She slowly laid on her side and pulled one leg up slightly so her ass was easy to reach. Stan watched her young body as she stretched out.
She put her hand on it and pulled at it. Stan felt like a lucky man and took command, “Good. Now wiggle it around a little.” While she started playing with the plug Stan slowly got undressed and lubed up his big dick. She stared at it as she pressed on the plug. Sally watched his hand rub it up and down as she wiggles the plug in her ass to mimic the motion. Her mind was trying to reason with her body, 'We're doing this for Billy.' Her body just looked at Stan rubbing himself. His dick was so big, her hand pressed hard on the plug. Stan watched the expression on her face until he could see she was ready. Then he lay behind her.
He slid up next to her and his dick touched her bare butt cheek. Sally groaned holding firmly onto the plug. “Now take out the plug and put my dick in just like that.” “Ok, but don't cum in me. I don't want to get pregnant.” Stan said nothing but waited for Sally to pull the plug out and grab his stiff shaft. Then she guided it to her hole like a pro. Her mind echoed, 'Doing this for Billy.' She rubbed the head against her slick ass. She could no longer hide her eagerness. “Good. Now arch your back a little and try to stick it in just like the plug.” She did as instructed and felt the head stretching her tender eager hole even more. She pushed back a little more and the head popped in. 'Billy.'
“Oh God!” Her body shook with the realization, the first dick in her ass. It was hard for her to fathom and had to look over her shoulder to see. She propped herself up on her elbow to get a better angle. Her hand was wrapped around the shaft, but the head was hidden. Stan's big dick just disappeared between her cheeks. She pulled it out and shook. She looked at it and couldn't believe the big head had fit in there. Then she pushed it back against her hole until it popped back in. She groaned and whined. “Remember what you learned about sucking dick? You got to show him you want it and enjoy it.”
Sally wasn't sure what to do her but body knew it was supposed to slide in and out. Her grip increased around his shaft as she pulled trying to slid it deeper. Her eyes looked into his and she smiled. She started arching and pressing back harder. Stan instructed her to lift her knee closer to her chest and then extend her leg back a couple times. Sally did so without questioning. Each time she lifted her leg Stan slid forward. When she extended her leg she could feel his big dick creeping deeper. When her grip on his shaft pressed against her butt she looked again. There was so much left, “It's so big.”
She shifted her hand to his hip for balance and leverage. “Good. Now rock back and forth.” She followed his guidance without question holding onto his hip as an anchor. It inched deeper as she rocked and she was beginning to get very excited, “Oh... it's getting deeper inside me!” Stan pushed and his dick slid even deeper, “That's the idea.” From Sally's point of view Stan's big dick began sliding in and out under it's own power, “Your cock is fucking my ass!” It was huge. It was alive. It felt amazing. Her body was beginning to tingle and pulse as she began fucking him back, “Don't cum in my ass.”
When Stan felt Sally's hand pull on his hip he knew she was really enjoying it. He started fucking harder and then revealed a secret. “Silly girl. You can't get pregnant like this. That's why people do it.” But Sally was breathing heavy and lost in the motion. It felt so exciting. Again she was trying to keep from having an orgasm, 'Don't cum. Don't cum. Don't cum.' Her eyes were closed and her mouth slack as she leaned on her elbow when suddenly she felt something press against her lips. Stan's voice crept into her ears, “George felt left out the other day. Maybe you could give him a little blowjob while we're practicing. Besides he gave you his spare butt plug.”
The voice in her head got louder as her sensations grew, 'Do not cum. Do not cum. Do not cum.' She felt George's dick push into her mouth as Stan fucked her ass and she blindly began sucking. She wasn't thinking about Billy. Just the moment. George pushed in further and began pumping into her throat. 'Don... Not... Cum!' She felt a rhythm between Stan's fucking and her sucking cock when her orgasm struck. It crashed over her like a giant wave. Sally couldn't hide it and whined around George's dick. Her body jerking with each rush.
Stan found the rhythm and buried his dick with each wave causing Sally to swallow George's dick to the root. She quickly became delirious from the attack. Her body was wracked with the intensity of it all. Stan began grunting and she felt something pulsing deep in her ass as his sperm squirted into her. Her brain repeated, 'can't get pregnant like this.' Which caused her orgasm to start anew and she drifted off on waves of pleasure. Soon after she realized the dick was gone from her ass and her mouth and Stan was in the bathroom. Her body was sprawled out on the bed. She was just catching her breath. Then someone was crawling in bed behind her again. She tried to regain her senses and struggled to move away.
George grabbed her hips and easily slid his dick all the way in to her already gaping ass. He was so deep. She knew she couldn't get away. But her body pushed back automatically and began humping his dick with her butt. George wrapped his arms around her, one hand on her breast tweaking her nipple and one in her groin rubbing her pussy. Sally's eyes closed and she groaned out loud as the sensations started again. She heard Stan's voice and felt a dick pressing into her mouth again, “That a girl. Now open wide.” This time it was Stan's big dick. She surrendered to the sensations as they fucked her from both ends. The two of them helped her practice until she was exhausted from orgasms and her ass was filled with cum. They put the butt plug back in, wiped her face, dressed her and sent her home.
As Stan pointed her dazed and buzzing body out the door he encouraged her, “Good work today. Billy is going to very proud.” Her eyes were glazed over as she turned to look at him. 'Billy.' Stan looked for any signs of life, “I think one more lesson should do the trick.” Sally smiled ear to ear. Her body pushed towards his but Stan turned her and pointed her towards the door again. “Later. You need to rest and do your homework.” Her butt cheeks tightened around the plug and as she walked away she noticed how much she liked the way it wiggled.
When she arrived home it was already past 5. Her father was there. As she crept in she wondered if she was going to need to explain herself. Her mind was still buzzing as was her ass. “Oh, honey. You just missed a phone call. George and Stan called.” Immediately her butt tighten around the plug forcing a small drop of sperm to drip down the inside of her leg, “Oh?” Her father set a note on the counter, “They would like you to come by this weekend to help take care of dogs while they're busy with something. Maybe spend the night.” Sally quivered at the thought, 'all night.' Her mind was uncertain but her body knew differently.
“I didn't know they had dogs.” her father asked questioningly. Sally replied quickly, “Yes. It's a temporary thing. Two of them.” and then to herself, 'big ones.' Her body quivered again, “I have to go to the bathroom.”