The Importance Of Stretching by tannim May 06, 2011 Tosh giggled at the feeling of his mom's fingers around his anus. His four year old butt clenched at the slippery digits rubbing more slippery stuff around it but he enjoyed it a lot. He liked her other hand stroking along his inner thighs and over his little balls and penis too, though. The bigger goat pressed a finger into his ring, then leaned in to kiss her son's foreskin covered penis tip. Tosh was quite excited to to play with the new toy he'd picked out, even if his mother told him that it was too big. She'd relented only because she knew he'd eventually be able to take it and he rubbed his hooves down her back hoping to get her to lubricate him faster. "Ready now, ready now!" He clenched his ass around her finger too tightly despite his claims. "Can I take it now, Mommy?" "Not while you're squeezing like that around my finger. You need to be a lot more relaxed to have a chance at the new toy." She pulled an old smaller toy out of the toy bag. It was slightly thicker than her finger and was nothing compared to the massive plug waiting for the boy to try to get in. "Alright, lets try this one first and see how you do." He made a cute grunt at her finger pulling out, then another at the wider thing pushing in. His ring fought her at first, even with it lubricated, but soon opened for the toy. Tosh tried to keep the strained look off his face, but couldn't. He could feel his bottom opening, but it wasn't doing it right. It had been a while since he'd last taken a massive toy up his butt and he was anxious to try it again. His mother hadn't had time to fuck him with her strap-on for nearly two weeks and he really missed it. The happy feelings when he was filled up and something inside was bumped were a lot of fun for the kid goat. Tosh took a deep breath as his mother suggested and tried to make his body relax. She didn't make it easy, though. The toy pushed in and out of his hole, aching at first, but soon just feeling intense. He made progress after about a dozen thrusts when he felt it slide in so much easier. Esme noticed it too, just before she added her finger to the penetration. Her son stiffened at the additional girth popping him open each time until he got used to it. The boy scooted back away from her suddenly and she watched in amusement as he took the toy and pumped it faster in and out of his butt. Tosh sat hunched over on the plastic lined bed with his legs spread to work the toy in. He knew his mom would want to see it and he enjoyed showing it to her. His soft penis and balls bounced a bit while he worked himself. While he enjoyed it a lot, his cock stayed cutely soft from being spent earlier between Esme's breasts. She had to keep him spent so he'd be relaxed enough to control his anal ring better. When he was too needy he was too tense to take a toy very easily. The fact that they both enjoyed draining him was just a happy side benefit. His cheeks flushed as he worked and at last he stopped and tugged the toy out. Esme set the new toy down near him to remind her son just how big it was, and Tosh flushed deeper. It was wider than his arm at the tip, before narrowing a bit behind the top bulb. The narrowing changed to widening immediately after that bulb, though, into a much downward slope to the fat base. The new toy was slightly bigger than the biggest toy he'd ever taken. That toy in the past had been a struggle and he'd had to have his mother's help to get it in. He still needed it. Tosh looked at it, then at the small toy he'd been using. About five of the small toys would fit inside the tip of the new one. "I can take it, Mommy!" He proudly reached for it before Esme pulled it away. She didn't try to stop him, his mother simply squirted the lubricant onto it very liberally and rubbed it evenly and generously on before adding a big blob to the tip. Her son watched it and scrubbed his fingers around his ring trying to open it a bit more. He had an intense look of concentration on his face while he worked to open up. Esme at last set the toy down, on the floor, and he quickly hopped of the bed to squat over it. The boy felt a bit worried when the bulb and his anal ring kissed. It felt huge, and was. His little toy from before was nothing compared to its size, but he scrunched his face up in determination and squatted onto it harder. His muzzle tilted up with his head at the increasing strain. He knew his anus had could take it and taken nearly as big before, but he didn't know how much it had tightened in the two weeks without regular working out. There was a lot of pain as his ring protest the wide stretching without practice and only Esme's hand grabbing his hips before he forced it in too fast kept him from hurting himself. She pulled him up and off while tears streamed from his eyes. "You're not ready, yet, Tosh. We need to get your bottom used to being penetrated again before that." He looked up at her and scrubbed his eyes with a fuzzy arm. Her smile made him smile. "Why don't you go get mommy's toybox and we can see about working you open tonight. You can try..." Tosh ran out of the room, with a bit of a waddle from the ache in his ass, to get her toys. When he came back he had her strap-on dildo harness over his shoulders and the box in both hands. Together they selected a few from the girth of an average banana to a half dollar and then to a soda can. The bulb on his new toy was larger still, but they two goats figured he could handle it when he could take the rest. Esme stood still for him to snug the strap-on harness around her broad motherly hips. He knew she liked feeling his small hands snugging the crotch strap up between her really soft pussy lips. She'd selected a nice long filling toy for herself to feel with each thrust and he got to push that in before the strap. Normally he'd pay more attention to it, but he was much too focused on his own penetration to worry about his mom's and only remembered to connect the harness to it when she asked if he had. Tosh lay down and looked up at his mother while he took the first one. It felt good filling him up. The second did too, though he had to take the half dollar size toy for a lot longer before getting comfortable with it. Her hips soon bumped against his easily with each loving thrust, though, and he was ready to move on to the next size up. He spent nearly an hour getting used to the soda can girth. It was amazing he could take it at all and he loved the rushing sound it made in his ears from the strain of taking it. Each time it went in his body tensed deep and hard for a long time, but finally his hole relaxed and his colon relaxed and he let it in. His young thighs quivered even without being used. They felt like jelly when she tugged them up to kiss his hooves. He just lay there panting and thinking about how amazing the new toy was going to feel once his mother decided he was ready for it. He hoped it was soon, but it took a while longer than he'd wanted. At last though, she slid in fairly easily and Tosh giggled tiredly when she squeezed his small balls. "Ok, Tosh, it's time for the big one." Esme didn't bother asking if he still wanted it. The look of excitement on his face told her he did. It had already been washed and all she had to do was re-lube it to try again. Her hips never stopped thrusting the smaller toy in while she worked. Tosh watched her the whole time. He saw her take a deep breath, then felt the huge toy's tip against his butt. His mother yanked her strap-on out and pushed the new one into the gaping boy hole. He yelled and kicked his legs out when the wide bulb popped into his ring and clenched his whole body at it's girth. It hurt, but no more so than most new ones. The thing slid in a bit deeper, then pulled back partially out. She went slow, his mind went blank to anything but the invading silicone and the amazing pressure on his little happy place hidden inside. It felt amazing. He moaned to the continued penetration. He squirmed at the ever increasing girth the deeper it sank and he yelped at feeling it pop past his deep inner ring so it could sink even further inside. The little kid whined as it did hurt and was glad his mom went so slow. Esme stroked over his little penis and bent to tug at his long saggy foreskin with her lips. She pulled it up to stretch it just past a foot long before rubbing his inner thighs and cock with her free hand. Tosh lay still and let her work. He basked in the fullness and pleasure his momma gave him. One hand jerked him off, one hand filled him up. Her breasts and pretty face gave him something to watch and by the time he'd taken most of it he was long past pain from the pleasure in his groin. Tosh came hard, and dry, with his erection fully hidden by his lengthy foreskin surrounding it. He felt nothing come out, but he didn't have to. It felt exotic, but good. His ass tried to clench from the pleasure but the silicone filled him too much. His orgasmic contractions just felt like one drawn out clench instead and his lips trembled from it. Before he came down fully, Esme pulled the toy fully out of him and leaned down to kiss him passionately on his lips. "That was beautiful, my love." "I took it, mom! Look, I took it!"