Speedy’s Discoveries 3
by @silvergunner

It was the day of the annual Sisterhooves Social in Equestria. Every year it was a long obstacle course where double teams of sisters competed to get to the finish as quickly as possible, completing the given tasks on the route as quickly as possible. It was considered the greatest show of sisterly bonding around, and was popular amongst not just sisters but also their families that came along to watch.

Along with the non-competing crowd that day was a young blue earth pony. He was there to cheer on his three friends and support them the best he could. He couldn’t enter due to his gender and the fact he didn’t have any sisters or even aunts or female cousins. But he was still there to support his friends, and was at that very moment looking around for them while walking through the enthusiastic crowd of spectators and potential competitors.

“Hey Speedy! You made it!” came a chirpy voice from nearby. He turned around to see Scootaloo looking at him. “You come to cheer us all along?” she asked.

“Of course” Speedy replied. “You here with Rainbow Dash?” he asked, and Scootaloo nodded. “How about Sweetie Belle and Apple Bloom? Their sisters here too as well?” he asked.

“Well Sweetie Belle and Rarity are here. Haven’t seen Apple Bloom yet. What with Applejack busy with the Cutie Map and all, its unlikely she’ll compete” Scootaloo replied.

“Yeah, its a shame really” came the voice of Sweetie Belle. She walked over to Scootaloo and Speedy and waved at them in greeting. “It would be nice if she came along t...” she started.

“Hi” came a dejected sigh. The three turned to see the young earth pony Apple Bloom was standing there in front of them. “I made it eventually” she commented.

“Nice!” Scootaloo replied. “Was Applejack able to make it after all?” she asked.

“Well, no...” Apple Bloom started, but was cut off by a mare behind her clearing her throat.

The other three gazed in stunned silence at who they saw in front of them. She was a really tall and bulky mare, with a fancily styled blonde mane, a flowery dress, and lots of cosmetics applied. “Well hello there!” she said in a deep feminine voice to all of them, following it with a smile.

“Sweetie Belle, Scootaloo, meet cousin Orchard Blossom” Apple Bloom sighed.

“Oh my, it is my extraordinary pleasure to make your acquaintance” the mare said. She then turned to Speedy and smiled at him in particular.

Speedy said nothing. He knew they were all talking but he wasn’t paying attention to what was been said. He was stunned instead by Orchard Blossom’s beauty, and his heart was racing with his feelings for her. It was love at first sight for him, and she was so stunning he went into almost a trance. The next thing he knew was Apple Bloom prodding him to get his attention, and him realising everyone else had ended the conversation and gone elsewhere.

Sighing and shaking his head, he reminded himself why he was there - not to crush after mares he had just met, but to support his closest friends, the Cutie Mark Crusaders. He followed them towards the baggage area, but he couldn’t divert his gaze from Orchard Blossom. The way her butt swayed from side to side while she walked was an almost hypnotic sight, and Speedy wondered how good it would look without her dress covering it...

“Erm Speedy, you alright?” came the voice of Scootaloo. “You seem a little off today” she added.

Speedy shook his head. “I’m fine Scootaloo. I just didn’t sleep very well last night” he ad libbed as an excuse. He felt the lust was spreading through his body and he clenched his hind legs together, fearing he was about to get a boner and potentially embarrass himself if anyone saw it.

As they walked through the field the Social was being held in, he suddenly noticed a refreshment table had been set up. “I need a drink, be with you soon” he said to Scootaloo and headed over towards it. He grabbed the first bottle of cider within his grasp and, after taking off the cap, downed it swiftly. It had a familliar light kick at the end which suggested it was alcoholic, and was just what Speedy needed at that point. He wanted a few alcoholic drinks to clear his mind of the image of Orchard Blossom’s backside.

Moving onto a second bottle, he looked around the area and thought about his life up until then. He and Spike were still going steady when he stayed at Twilight’s house, but he had recently flirted with Big McIntosh. As a result he was getting around Ponyville more than normal, as the Apple family had made him their chosen courier for lightweight items, no doubt thanks to Mac’s recommendation. At the same time he was still helping out at Twilight’s library and kept Spike company when both of them were alone or horny.

Things were getting better in Speedy’s life, but he still felt a lacking feeling in his heart. He had two boyfriends who he loved spending time with, but neither felt completely a part of his heart. He yearned for someone more sensual, and he felt that Orchard Blossom could be that pony to fill the gap in his heart. If only it wasn’t here in public they could maybe talk about it...

As he put down the third empty bottle of cider, he looked over towards the stage and saw that the opening musical presentation was about to start. He remembered that Apple Bloom and Applejack were due to perform that year, and hurried over to watch. As he did though he remembered Applejack wasn’t there that year, and wondered who could possibly fill in for her. He let out a gasp as he saw just who was going to.

After Apple Bloom was invited on stage, she stood to one side as Orchard Blossom stood beside her. After a moment of silence, Apple Bloom started singing and Orchard Blossom joined in. Speedy was transfixed by what he heard. Although Orchard Blossom’s singing voice was not what could be considered stellar compared to the other musicians in Ponyville, Speedy couldn’t divert his attention. She looked even more beautiful singing than she did when she was just talking.

As the song continued, his imagination began to wander. He imagined her singing for him on a long summer night as they sat beneath a tree together. Then as the sun set, he would kiss her on the lips then make love to her gently...

His thoughts were disturbed as he heard clapping coming from the ponies around him and realised the song had ended. He looked at the stage and could have sworn had seen Orchard Blossom winking at him. He nodded back, then turned away while the applause continued. Right now he wanted to go and clop rather than clap as his hormones surged through his body.

He felt if he stayed any longer there he could possibly embarrass himself in front of all his friends. He was aware that his member hanging between his legs was fully erect, and didn’t want anyone to see it. He tried to relax and went towards some bushes to cool down. He decided that when his erection softened, he would tell Apple Bloom he was ill as an excuse to go home early.

As he passed by the pile of luggage left by the various ponies attending, he noticed a flowery handbag besides Apple Bloom’s messenger bag. He gazed at it and saw that it read “OB”. Suddenly a plan came to mind. He wanted to see Orchard Blossom again, but it wasn’t a good time. So why not plan to meet her the next day and hang out in private?

He rushed to his bag and drew out a pencil and paper. He wrote quickly “Meet me for drinks at the furthest orchard at Sweet Apple Acres tomorrow at noon - your secret admirer”, folded the paper, and stuffed it in the handbag. He then grabbed his bag and ran towards some nearby bushes to sit there for a few minutes. He tried to distract himself from his horniness by taking a book Twilight had loaned him out of his bag and starting to read it. Reading about boring advanced mathematics worked to calm his lust, and after a few pages of sums his boner was gone.

After putting his book into his bag, he slung it over his shoulder. Jumping to his feet, Speedy trotted over to where Sweetie Belle was. “Hey Sweetie Belle, could you tell Apple Bloom i’m having to go home? I’m feeling a bit unwell from... the heat” he said.

Sweetie Belle looked a little sad but nodded. “I’d hoped you stay for the race, but if you’re feeling unwell its best you get home and have Twilight check you over” she said. “I’ll tell the others and we’ll hang out the day after tomorrow” she added, smiling at him.

“Thanks Sweetie Belle” Speedy replied. He then turned away and started walking slowly away from the field. He took one glance back to see the others lining up for the race, then galloped quickly into the distance back home.

The evening passed slowly when Speedy arrived home. After cooking dinner for himself, Spike and Twilight, he spent the rest of the evening reading books. He was trying to divert his attention from thinking about what he saw in Orchard Blossom, but was failing and just couldn’t seem to relax. It was nearly 4AM before he finally fell asleep from sheer exhaustion after hours tossing and turning in his bed.

Due to the sleepless night it was already 11AM by the time he finally woke up. Rushing downstairs he grabbed half a dozen bottles of alcoholic cider and a package of cupcakes from the “treat cupboard” and put them straight into his bag. Although Twilight had warned him not to drink too much alcohol, Speedy felt it was justified to drink while socialising. All the other ponies he knew drank much more heavily than he did, after all.

He galloped through Ponyville at top speed, trying to reach the meeting spot before the clock struck noon. He nearly knocked down a pony carrying a large crate of oranges as he turbocharged through the usual lunchtime crowds. He never stopped galloping until he had zoomed through the gate into Sweet Apple Acres, and covered the last stretch right to the back of the many Orchards. He finally reached the tree at the very back of the farm, on a hill overlooking the lands beyond. It was a inspiring and scenic view, and one where he was sure they could have some peace and quiet together.

Speedy sat down underneath the tree and sighed. He unpacked his bag, first placing down a picnic blanket, and then putting the bottles of cider and muffins on one side of it. He sat down in the centre of the blanket and waited. He hoped Orchard Blossom would turn up, but a growing feeling of doubt within him suggested she wouldn’t. All he could do was stay positive and hope she turned up.

Minutes passed and Speedy’s worries intensified. He just hoped he hadn’t scared her off. A horrible thought entered his mind and he wondered if the note went in somepony else’s handbag. He was seriously considering leaving and lying low in case things had gone wrong and he ended up a laughing stock. He was about to stand up and do so when he heard footsteps from behind him.

He turned his head around and gasped at who he saw in front of him. Orchard Blossom, one of the most attractive mares he had ever seen, stood in front of him. She took a good look at him before winking again. “So you are the pony who asked to see me?” she said in her low pitched yet still feminine voice.

“Yes... I am” Speedy replied, his speech stuttering a little. “I wanted you to come here and have a picnic with me because...” he started.

“Because?” Orchard Blossom asked, walking closer to him until they were inches away from each other.

“Because I love you” Speedy finished. “You’re the most beautiful mare i’ve ever met” he added.

He expected Orchard Blossom to act shocked but instead she just gave him a wide smile. “Oh my, its so nice to know such a handsome young stallion as yourself likes me” she replied. “Especially one i’ve had my eye on every since I saw you with my cousin” she added, giggling.

Before Speedy could do anything else she had walked even closer to him, before planting a gentle kiss on his nose. Speedy gasped in surprise, his happiness levels rising as the mare he had crushed on was getting sensual with him. He put his arms around her shoulders and pulled her close to him in a warm hug. “Why did you have an eye on me?” he asked, before returning the kiss on her nose.

“Well it was almost impossible to notice your assets at the Sisterhooves Social, my dear” Orchard Blossom replied. “Even now you’re incredibly noticeable” she giggled, blushing a little.

Speedy looked down and gasped as he saw his member was fully erect again. The kissing had driven his lust over the edge and his dick was standing to attention as thoughts of using it on Orchard Blossom flowed through his head. “Umm... yeah... about that” he blushed. “You’re so beautiful you turn me on...” he admitted.

“You know Speedy, I must confess I’m a bit of a size queen, and I like big dicks” she giggled. “And you’re one of the biggest I’ve seen. There’s so much I want to do with it right now” she added.

“Like what?” Speedy asked. He put a hoof under his body and felt his hard member. Even though he was still growing up, it was over eighteen inches long and standing to attention.

“I’d like to suck it first, if you pardon my coarse language” she said. “Big dicks tend to taste nice, and i bet you have a load of delicious cum saved up for me...” she added, giggling. “May I?” she asked.

Speedy nodded in response to her question. He dropped to the ground then rolled over onto his back, with his black erection pointing up in the air. Orchard Blossom walked over towards him and gazed at his member with a look of pleasant surprise on her face. She gripped it with both of her hooves and began rubbing it gently, her hooves running up and down his shaft. Speedy began breathing heavily as the mare he lusted after began massaging his cock with her hooves.

After half a minute of rubbing, Orchard Blossom then kissed the tip of his cock. She then began licking his shaft up and down, with the young stallion groaning in pleasure at the sensation of her warm wet tongue on his sensitive erection. She moved her head over and opened her mouth before diving her head downwards, the stallion’s cock sliding into her mouth. Speedy moaned even louder as he felt her bob her head up and down on top of his member.

Suddenly Speedy pulled himself back before he could climax. His cock slid out of Orchard Blossom’s mouth as he got into a sitting position. “Is something wrong, Speedy?” she asked him.

“I’m fine, but I think you deserve some attention too” Speedy smiled. “You know, ever since I saw you, i’ve imagined buttfucking you” he commented, blushing a little. “Would you mind if we...?” he asked.

Orchard Blossom looked uncomfortable at this. “Well the thing is Speedy... I don’t think you’ll like it when you see my flank...” she said. “I’d love to... but if you see what I look like back there...”

“I’m fine with it. I love you” Speedy smiled. She nodded in response and got to her feet, before turning around. Speedy got to his feet and used his hooves to push the hem of her dress up. “I can’t until I slide into you, Orch...” he started. He then stopped when he saw below the dress was not Orchard Blossom’s vaginal entrance, but instead a huge stallion member, even bigger than his own, and it looked very familiar to him... “You’re... Big Mac in a Dress?” he gasped in surprise.

“Eyup” came a sad sound of confirmation from Orchard Blossom, however it was in a gruff masculine voice rather than her low feminine one.

“It was you all along?” Speedy gasped. “Why did you dress as a mare?” he asked.

“It was for Apple Bloom. So she could win the Sisterhooves Social even when her sister Applejack wasn’t available” Mac replied. “It was foolish and it didn’t work, and we were disqualified from the contest for poor sportsmanship” he added.

Speedy smiled as he imagined Mac attempting a delicate obstacle course. “That was nice of you to do it for Apple Bloom” he replied. “But why did you crossdress again today? For me?” he asked.

Mac shrugged. “Well, you seemed so taken by Orchard Blossom I didn’t want to disappoint you... but I suspect you are disappointed anyway” he sighed. “I’m sorry if you wanted a sexy middle age mare and got plain old me instead” he apologised.

“To be honest Mac, i’m happy anyway” Speedy replied. “I mean, I just got my penis sucked by my favourite stallion” he replied. He then took one of his hooves and ran it down Mac’s shaft. “Plus, I did promise to give you some attention and i’m not going back on that promise” he added.

Speedy grabbed Mac’s member with both of his hooves and began rubbing it up and down, feeling it thicken and lengthen as he held it. He then slid himself underneath Mac’s body, and underneath the dress Mac was wearing. He was now in a position where Mac’s cock was directly against his face. Speedy opened his mouth and gently took the first two inches of the larger stallion’s cock into it. With the tip in his mouth, he sucked it gently.

He heard groaning come from above him with Mac seemingly enjoying the sucking of his tip. Speedy pushed himself forward and more of Mac’s cock slid into his mouth. He began bobbing his head up and down on Mac’s cock with more and more of it going into his mouth and pushing against the back of his throat.

He could barely manage half of Mac’s Stallion cock in his mouth, but it was enough as he heard Big Mac yell from above him in climax. Suddenly Mac’s cock started shooting wads of cum into Speedy’s mouth, with the younger stallion swallowing every mouthful as his crush pumped the contents of his balls inside Speedy.

After swallowing most of Mac’s load, Speedy pulled away and as the larger stallion's cock left his mouth, he let the last few spurts of cum splatter over his face. “Enjoy that Mac?” he asked the bigger stallion.

“Eyup” Mac replied happily. “However it might be nicer if you buttfuck me as well. Like I say I’m a size queen for stallion cock” he chuckled. “Want me to take off my dress to make it easier?” he asked.

“No, I’d like you to keep it on. It makes you look prettier” Speedy smiled. “In fact, if you could, I’d like you to speak like Orchard Blossom please” he added.

Mac paused in contemplation for a moment. “Oh my young man, I hope you’re planning to put that thing of yours to good use and give this old girl a damn good buttfucking” he said in his falsetto, chuckling a little after finishing the sentence.

Speedy didn’t have to be told twice. He scraped the cum off his face and rubbed it onto his cock to lubricate it. He then climbed out from under Orchard Blossom’s dress and got to his feet. Planting his front hooves on the larger pony’s back, he lifted his body in the air, and the tip of his rock hard member poked against Mac’s rear ending. “This is for you, Orchard Blossom” he commented, before pushing his hips forwards.

“Oh my!” Orchard Blossom exclaimed as he felt Speedy’s hard member slide in his backside. He began moaning as Speedy began thrusting his cock in and out, going deeper and deeper into his butt. He always liked getting buttfucked, and Speedy was one of the best studs around for a rear delivery that felt damn good. However he felt Speedy was going a bit more vigorously than normal today, and wondered if the Orchard Blossom masquerade was working for the younger stallion...

“Whoa... so... tight...” Speedy mumbled as he continued thrusting in and out of Orchard Blossom. Everything felt more intense than normal, and Speedy knew it was because of how his partner’s teasing and the attraction to their masquerade had caused a build-up of his lust. The crossdressing by Mac had worked for him, and he was determined to keep going until his partner orgasmed again.

Moments passed, with Speedy thrusting in and out increasingly harder and faster. Both stallions were moaning in pleasure, and when they could take no more, both of them orgasmed at the same time. As pleasure surged down Speedy’s spine, he felt his cock blast a torrent of cum into Mac’s backside. Below him, Mac blew a second, smaller load from his cock onto the ground.

They stayed in the same position for a moment until their orgasms subsided and their breathing returned to normal. Speedy pulled himself backwards and steadily all eighteen inches of his member slid out of Mac’s backside with a small pop. He moved around to Mac’s face then kissed him. “Feel like a Cider, Orchard Blossom?” he asked.

“Oh my, that would be quite the perfect aftermath to the great fucking I just got” Mac replied in his falsetto. Both ponies looked at each other and burst out giggling. Mac sat down under the tree while Speedy grabbed a bottle of alcoholic cider each for them both. They pulled off the caps of each one and laid there, drinking them slowly as they watched the land before them.

“You know, I worried the letter might have been misplaced or be ignored. Or that you didn’t expect me to be here at all – maybe someone else would be” Speedy said. “I’m glad it worked out though” he smiled.

“Well in actual fact, you put it in the wrong bag. Its just as well Apple Bloom spotted it. She fished it out and gave it to me when she realised it was from you” Mac chuckled. “She knows we’re here and what we’ve been doing - she doesn’t mind” he added.

Speedy blushed, realising his plan was close to going wrong, but ended up going fine anyway. “Thank you for such a great time though Mac. I love you” he commented. “Could you do something for me in future maybe?” he asked.

“What would that be?” Mac asked. “I’m always up for a buttfucking and a cider whenever you want after all Speedy” he commented.

“...crossdress more often. I enjoyed you masquerading at Orchard Blossom” Speedy replied.

Mac looked confused for a minute then broke into a big smile. “Why Speedy, I do declare that I will do so in the future for you. Its nice for a lady to break out her fashion sense, especially for such a great young stallion” he said in a falsetto. Both stallions chuckled at this, and after downing another cider each, laid there against the tree for the rest of the afternoon happily.

- The End -