Lauren stared at Tracey’s ring as she listened to her explanation. She was almost in disbelief as Tracey reiterated how she secured her man. “It was really quite simple. I sucked his dick everyday whenever he wanted it for a month. Swallowed every load with a smile. On exactly the thirtieth day he took out his dick and I refused. I explained that it didn’t feel right that I had committed myself to him and he hadn’t made a commitment to me. He argued a bit but then I told him that as soon as he was willing to make a commitment to me I’d commit all my holes to him.”
Lauren shook her head, Tracey wasn’t that good looking but she was now engaged and Lauren wasn’t. Lauren congratulated Tracy again and began thinking on how she’d pull the same deal with Joe. Lauren and Joe had been together since college and although they’d talked about engagement and marriage, he’d never been especially committal.
As Lauren left her friend and started to walk home her mind was racing. Sucking Joe off for a month was no problem, it was giving up her back door that gave her hesitation. As she walked she remembered how painful it was when she lost her virginity to him. She’d tried stretching herself out before that night, but nothing she’d done prepared her for Joe’s nine inch cock.
Lauren whipped out her phone, she knew what she needed to do. She quickly texted her friend, “Hey, do you want to grab a drink? I have a big ask of you”
In moments she got a response and headed to the bar. Her friend Jimmy was waiting for her, two drinks in front of him. Lauren gestured to an empty table away from everyone else and Jimmy grabbed the drinks. They settled in and Lauren laid out what she’d just heard.
Jimmy laughed and shook his head. He knew where Lauren was headed with this conversation and he was getting excited at the prospect. Lauren finished her story and paused. Slowly she continued, “So you know I’ve told you how big Joe is. And I know you’ve been doing this for years, so I was wondering if you could help train me a little for this.”
Jimmy made sure he wasn’t smiling too big. He was happy that he didn’t flaunt his sexuality. Everyone assumed he was just gay but although he preferred men, Lauren was in a sweet spot for him. At 5’6”, flat chested, and toned from years of playing and coaching basketball she looked like a textbook tomboy. She kept her brown hair short and didn’t wear much makeup. On top of all of this, Jimmy knew that Lauren had only been with one man. If he played his cards right he could take her anal virginity and break her streak.
He slowly agreed, “I can help, I’ll give you a list of stuff to buy to start training but, what you really will need is somebody pushing your limits.” Lauren nodded along but didn’t look comfortable. Jimmy continued, “Nothing crazy, but if you train this coming week, I might be able to give you a hand next Thursday or Friday. We can play it by ear from there.”
Lauren agreed and finished her drink. She’d barely reached the door when her phone buzzed. Jimmy had listed out a couple butt plugs, a 9 inch dildo, and more lube than she thought could possibly be necessary. In minutes she had ordered everything online and got confirmation it’d be delivered the following day. She hurried home to her boyfriend.
Joe was on the couch watching TV when Lauren walked in. He nodded to her and kept watching, he only really looked at her when she turned the TV off. Before he could say anything she was on her knees in front of him pulling at his sweatpants. Lauren loved Joe but sometimes wondered if she could do better. She took a hold of his cock and began licking the length of it as she held the base of the shaft firmly. Joe was a bit of an underachiever, not that Lauren was excelling at life as a basketball coach. Joe’s cock was almost erect and Lauren smiled as she kept licking it. He might not have been the greatest boyfriend but he was the only one she’d ever had and with a cock like this, the only one she ever wanted.
She opened up her mouth and worked the head of his cock in. It always took a little adjustment but by timing her breathing and pushing past the pain she began pumping the first three inches of his cock into her mouth. She’d never be able to deep throat his member, but as Joe looked down at Lauren he knew she was doing her absolute best. He felt it coming and reached down to hold her head. Lauren was used to this and maintained eye contact and he began thrusting into her face. She began worrying about breathing as she felt him shudder and release into her mouth.
When he was done Lauren made a bit of a show of wiping the cum from her chin and depositing it in her mouth. She really didn’t like the taste, but she was willing to do whatever it would take. With a big smile she swallowed his seed. Wanting to drive home the point she licked his cock clean, making sure nothing went to waste.
The next day her package arrived. Lauren was careful to hide it from Joe as she took it into the bathroom. Most of the drawers had her stuff in it and she knew Joe wouldn’t look through them. Everything but the smallest plug and the lube was quickly buried. Lauren had reread Jimmy’s directions and knew what she was supposed to do. Starting with the smallest plug, she would insert it in the morning and wear it all day. Whenever she had the chance she was supposed to pump it in and out of herself. She looked at the pathetically small toy and chuckled a little. At three inches long and only an inch and a half at its widest it didn’t come close to comparing with Joe’s cock.
Nevertheless she knew she needed to start somewhere, so she stripped down. She admired herself in the mirror briefly, you could just barely see the outline of her abs. She wasn’t thrilled that her pectoral muscles showed more than the fat of her tits, or that her pussy lips hung from her bare cunt, but overall she was happy with her body. She squatted down and applied some lubricant to the plug. She put a little lube on her pointer finger and reached between her legs. It felt cool but nice. She applied pressure but nothing happened. She tried to relax her muscles and only after several minutes was she able to get a single finger into herself.
She knew she didn’t have all day so she decided to take a different approach. She got up and walked to the toilet. She lowered the seat cover and set the plug on it. Lauren turned around and slowly lowered herself down. She adjusted slightly but felt the tip of the plug line up correctly. Hoping for the best, she dropped herself to the seat. Lauren let out a silent cry.
A couple hours later Lauren was still getting used to the sensation. She knew the plug wasn’t that large but she felt oddly full and constantly aroused. She let Jimmy know that her training had started and he congratulated her. He also followed up, “So you should come by this Friday night. My roommate and I will get you set to impress your man.”
Lauren wasn’t really feeling more people being involved in this but she’d met Jimmy’s roommate and she would probably have some good input. She was a little overweight and very butch, even for a lesbian. Lauren wasn’t super comfortable but it couldn’t be considered cheating if she was just getting help from a gay guy and his lesbian roommate with the pretense of learning how to please her boyfriend. Lauren’s head hurt as she tried to justify why this was okay.
Before Lauren knew it Friday had rolled around. She’d swung home before going to Jimmy’s, making sure her man was properly drained before telling him she was going out. Joe was fine with the idea and didn’t ask for any details. He was curious if she had started cheating on him, but with her worn out cunt he was sure that wasn’t the case. He thought again and decided even if she was, it was worth all the cock sucking she’d been doing.
Lauren knocked nervously at Jimmy’s door. Mackenzie opened the door. Lauren smiled at the shorter women and was let in. Lauren wondered what Mack’s role would be tonight, and she wasn’t super comfortable with the fact that she was just wearing overalls with her fat tits hanging out. Lauren chuckled to herself when she realized she probably looked a little butch herself, wearing a loose t-shirt and long basketball shorts.
Jimmy was mixing drinks and brought one to Lauren. She was relieved that the reason for her visit didn’t come up right away, and instead they all had a couple of drinks and just chatted. Two hours in, Lauren was feeling comfortable enough and finally broached the topic, “So, how is this all going to work?” She looked from Jimmy to Mack, and back to Jimmy.
Mack was the first one to speak up, “I think Jimmy might need another drink before he’s ready for this, but we can go back into my room and I can see how you’re doing.” Lauren would normally have objected, but this is why she’d come. The two women got up and went to Mack’s bedroom.
Lauren choked a little when she saw all the toys Mack had displayed on her bed. One in particular had to be bigger than Joe’s cock and had Lauren’s mind reeling. She dreaded the idea but she wondered if she could ever fit something that size inside of her. Mack took Lauren’s hand and led her to the bed. Lauren stopped short of the bed. Mack smiled, “Pick whichever one you want to start with and strip down.” Lauren hesitated before picking a long knobbly dildo. It was much longer than her plug, but the diameter of the largest knob was about the same size.
Lauren stripped down, hesitating with her panties. She knew Mack was behind her but she didn’t expect to feel hands grab her panties and pull them down. “Now bend over.” Lauren did as she was commanded. Mack tapped Laurens ankles and Lauren reluctantly spread her legs. She rested her forearms on the bed and tried to clear her mind.
Mack had to hold back a chuckle as she looked at this girl’s roughed up cunt. Jimmy had said her boyfriend had a big cock but it must be massive to take what must have been a pretty little pussy and turn it into the flappy cunt before her. It was comical that this girl wanted the same thing done to her ass. Mack knew that will a little worked she could probably get that stupidly large dildo of hers into Lauren. Too bad they wouldn’t have time for that tonight.
Mack cleared her throat, “Ok honey, hand me your pick.” Lauren complied, “I’m going to walk you through what I’m about to do, if at any point you feel uncomfortable please let me know.” Mack knew Lauren wouldn’t stop her at this point. “Now I’m going to place my hand on your ass, see not too bad. I’m going to pull your toy from you.” Mack ran her hand to the plug and yanked it out. Lauren’s ass made a plopping noise as it quickly closed up.
Mack smiled, “Now I’m going to eat out your ass a little. Try to relax and enjoy it. To help you relax, I’m also going to press a vibrator against your clit.” Lauren did her best to relax as she felt the vibrator make contact. She was almost comfortable and able to enjoy the sensation when she felt the distinctly wet and warm sensation of a tongue. As the shock wore off Lauren began to enjoy the pressure circling her rosebud. Nobody but Joe had probably ever seen her asshole and now this woman was circling it with her tongue, getting closer every rotation. Lauren was actually wanting it when she felt the tongue pressing against her hole. Being much smaller than the plug and with Lauren finally relaxing, Mack’s tongue entered with ease. Lauren fought the urge to pull back. She settled in and tried to enjoy the new sensations.
Mack pulled her face back. To Lauren’s surprise she actually missed the sensation, although the vibrator was still feeling nice, and Lauren was confident she was going to cum tonight. Mack adjusted herself and squirted some lube on the toy Lauren had chosen. She lined the tip of the dildo up with Lauren’s asshole and pushed it into her. The dildo was halfway inside Lauren’s ass before it started to hit resistance.
Lauren had enjoyed every knob of the thing but could feel that Mack didn’t have the right leverage. Once again, surprising herself, Lauren reached back and took the vibrator from Mack’s hand and held it against her cunt. With her hand’s freed Mack began pumping the toy in and out of Lauren’s ass. She’d pull a couple knobs out of Lauren and then push more in. In minutes the whole thing was in Lauren and she could feel her orgasm building to a climax. As she came she collapsed down onto the bed. She was so relaxed she barely registered the hand that had slipped into her pussy. It was smaller than Joe’s cock and she didn’t especially mind. It was pulled out just as quickly as it had entered her.
Lauren rolled over to see Mack, completely naked licking her forearm and wrist. Mack was pretty frumpy looking and clearly had never been to the gym. Lauren couldn’t understand how anyone could find that attractive, but it was non-threatening to have that as the person playing in your holes. Lauren was a little surprised when Jimmy walked in with drinks. She tried to brush it off and be cool. It wasn’t until she was standing that she realized the dildo was sliding from her ass. It made a dull sound as it hit the floor.
Jimmy laughed and handed her a drink. Mack took hers and started drinking. Jimmy looked Lauren up and down and couldn’t wait for what was coming next. He looked at the toy on the floor, “Is that as big as she can go? I thought you were going to be training her, not fucking around?”
Mack gave him a fake look of shame and kept alternating between licking Laurens juice from her hand and sipping from her drink. Lauren looked a little embarrassed and took another big sit of her drink. Jimmy reviewed the toys and found one he liked, it was a little smaller than his own cock but was twisted like a giant screw. “Lauren, lets relax a bit and I’ll give you some real training.”
He left the room and Lauren followed. She had an idea of what was coming but really didn’t like the look of that dildo. Her drink was somehow already empty when they got back to the living room. Without her asking Jimmy gave her a new one. Mack slinked into the room as Jimmy and Lauren sat down. “So there are two ways I see this next round going. We can either try some more of what Mack was supposed to be doing, or I can treat you like one of my fresh bottoms.”
Lauren looked at her half-finished drink. “Train me like a bottom.” Lauren had a higher opinion of herself than to believe the words she was saying, but they still left her mouth. She downed the rest of her drink, which she was pretty sure was just vodka and lime at this point.
Jimmy got up and took the empty glass from her. He set them in the kitchen and came back with what looked like belts. He tossed them on the couch and pulled a cushioned chair out in front of Lauren. Mack had seen this before, but this was the first time that it was Jimmy doing it to a woman. She couldn’t help but casually finger her pussy.
Lauren let herself be led to the back of the chair. She faced the back and Jimmy slowly bent her over it till he face was in the seat, her feet were barely touching the ground and her ass was completely exposed. She didn’t resist as he bound her hands and feet to the chair. It wasn’t too uncomfortable but it was clearly not purpose built for this use. Jimmy put a strap on the back of her head and moved a gag to Lauren’s mouth. “What is this for?!?!” Lauren pulled on her restraints.
Jimmy patted her head, “Hey, hey. Don’t worry, this is more for me than you. I do this with my bottoms, I figured I’d do it to you too. I have a good idea of what somebody can take, and even though you’ll feel like I’m hurting you, I won’t do any real damage.”
Lauren hesitated another minute before opening her mouth and accepting the gag. Mack got up and went to her room. She grabbed her vibrator, a bottle of lube and her comically large dildo. She returned to the room as Jimmy was warming Lauren up with some ass slaps. Her cherry red cheeks contrasted with the paleness of the rest of her body. Mack set the dildo down on its side and straddled it as she watched Jimmy get to work.
When Jimmy was confident she’d had enough of the slapping he picked up the screw shaped dildo. He borrowed some lube from Mack and returned to Lauren’s ass. He tested her with a finger and entered her with relative ease. He pressed the tip of the screw to her rosebud, “Relax darling, the more relaxed you are the more fun this will be.” Jimmy laughed at his cruel words and slowly twisted the dildo into her.
It steadily entered her body and before Lauren realized it she was being stretched to new limits. Jimmy could see the skin around her asshole stretching. Well before he was in any danger of tearing his friend, he pulled the dildo out. Lauren breathed a sigh of relief. She was convinced that she was going to get ripped apart and was happy Jimmy knew to back off. As it started again she tried to resist. Jimmy could feel it, but the beauty of this dildo was that as she squeezed on the twisting shaft, she actually held it in better. Jimmy barely changed tempo as he spread he hole farther and farther apart. Eventually Lauren couldn’t take it and cried out as she released. Jimmy took the opportunity to stretch her even farther. Mack came for the first time that evening as Jimmy ripped the dildo from Lauren’s hole.
Jimmy continued this process of twisting the dildo into his friend and ripping it out until he finally got it fully inserted. He left it in and came around to Lauren’s face. “Well there you go, that wasn’t so bad, was it?”
He removed the gag so she could speak, “Is, is that whole thing in me?”
Jimmy smiled, “Yup, bit bigger than that plug you’ve been carrying around. Only way you’re going to take your man though.” Jimmy slipped the gag back into Lauren’s mouth. Lauren was oddly relieved. Compared to what she went through to take Joe’s cock in her pussy the first time this really wasn’t that bad. No embarrassing crying or bleeding or waiting for her hole to heal so they could try again. If it just took a couple nights like this, she’d be happy.
Jimmy pulled the dildo from her ass and repeated the process another couple times till he was sure the stretching would hold. As he was admiring his work Mack approached Lauren, “Hey, since I was nice to you with my training, can I have a little fun before we call it a night?” Lauren assumed she meant fisting her again and nodded yes.
Mack practically ran to her dildo and began rubbing lube on it. Jimmy backed out of her way and let her get to work. Lauren felt the somewhat expected sensation of an arm reaching into her pussy. Mack gave her a few good pumps with her hand before adding in her other arm. Now Lauren felt a slight stretch. It wasn’t unpleasant but between her asshole begin filled and now her pussy she was feeling beyond bloated. There was a sensation inside her though that she couldn’t quite place, but she absolutely loved it. It was like the wall between her pussy and ass was filled with sparks of pleasure. She felt another orgasm building as the arms were removed.
The next sensation wasn’t as expected. She felt every side of her pussy being pressed on. It didn’t take long for her to realize that the favor for Mack wasn’t the fisting but that large dildo she’d had on her bed. Lauren was relieved but a little disappointed in herself as the dildo made its way deeper and deeper into her body. Mack was also surprised at how little resistance there was. Sooner than either of them expected Mack had gotten it all the way into Lauren’s cunt.
Jimmy couldn’t take it anymore and nudged Mack out of the way. He finally stripped down and got behind Lauren. Jimmy knew that his cock was nothing compared to Joe’s but for this girl’s asshole it’d be just fine. He pulled the screw dildo from her hole and lined up his head. Relishing the fact that he had the first cock that’d entered this hole and the second cock period to enter this girl, he pushed in.
Lauren couldn’t express how much she loved the sensation of her pussy being filled to it’s breaking point while she was getting fucked in the ass. Her mind was reeling as her orgasm built to an overwhelming wave of pleasure. She went limp and just enjoyed the several minutes of rocking as her friend fucked her ass. She was surprised as the cock was pulled from her without it finishing. Before she knew it her gag was removed and a dick was in her mouth. Unlike Joe’s, she could deep throat this one and after just a couple pumps she felt him release in the back of her mouth.
Jimmy staggered back. Mack pulled the dildo from Lauren’s pussy and started undoing the straps. When she was released she tried to stand and crumpled on the floor. It took another couple minutes before she had enough strength gathered to stand. Nobody said anything as they got dressed. Lauren was headed for the door when Jimmy stopped her. “Hey, aren’t you forgetting something?”
He was holding a butt plug that was three inches in diameter and six inches long, easily much larger than the ones Lauren had bought, but not that different from what had been in her tonight. Lauren walked over to him and put her hands on the wall. Jimmy pulled down her shorts and worked the dildo into her ass. He gave her a hard slap and she was out the door. As Lauren rode home she came up with tones of different ways to justify what had happened. By the time she was walking in, the whole thing didn’t feel like cheating at all. Joe was on the couch and Lauren didn’t skip a beat kneeling down in front of him.