• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • High School Friend Has A Secret Ch. 03

High School Friend Has A Secret Ch. 03

12

Waking the following morning I could think of nothing but my amazing night with Katie. Everything had happened so fast that I barley had time to take it all in. I wanted her again so badly. I laid in bed for a long time after I awoke, fantasizing about fucking her all over again. I still wasn't sure how she'd feel about our fuck the morning after but I prayed she wanted it again as badly as I did. I finally dragged myself out of bed and grabbed some shorts. Walking out my bedroom I headed directly for Katie's room. To my dismay, however, her door was closed. I didn't want to bother her but I could think of nothing but being with her again, "Hello?" I said as I knocked on her door.

"Hey," I heard in her normal perky voice, "I'm just getting dressed, I'll be out in a minute, don't go anywhere."

"Ummm O.K.," I mumbled through her door. What did she mean by 'don't go anywhere?' That had to be a good sign. She certainly didn't sound like she felt awkward or embarrassed. I could here her rummaging around in her room and decided to give her some time to get ready. I headed for the kitchen to start breakfast; I could never make it more than a few minutes after waking up without something in my stomach. Not more than 10 seconds after I made it in the kitchen I heard Katie's door open. My stomach twisted with nervousness, I tried not to notice that she was heading for the kitchen as I buried my face in the fridge, pretending to look for food.

"Last night was incredible," I heard from a sexy voice behind me. At the same time my stomach untwisted and my cock began to grow. I was so happy that there wouldn't be any awkward situation that I'd have to deal with. I was glad that we could just forget about Brittney and enjoy ourselves, no strings attached. Katie and I were luckily on the exact same page.

"Well I'm glad we're agreeing about something," I said as I turned from the fridge towards her. I instantly noticed that she was not really getting dressed like she said she was. She was standing there in the doorway of the kitchen wearing nothing but a sexy little black outfit; though I'm sure it's not a complete 'outfit.' Katie was wearing a tight black garter with dark stalkings that accentuated the bulge pushing against her tiny black thong. As my gaze flowed past her thin waist my eyes stopped at her beautiful breasts, barley hidden in a small black bra. Her long dark hair was pulled back behind her head in a pony tail and she was staring right at me. I couldn't say anything, I was at a loss for words.

"Well don't just stand there staring at me like an idiot, get over here," she said with a large grin creeping across her face. Shutting the fridge behind me I started for her. Rushing towards her my cock was already completely erect, and I began kissing her almost violently. I buried my tongue deep into her mouth, releasing all the tension I had felt about the morning after. As we passionately kissed I began groping her perfect ass with both hands. Each cheek in one hand I massaged her round ass and began making my way towards her asshole, I was so incredibly horny, I couldn't last any longer without her. When my fingers finally did find their way down to her tight little asshole she broke our kiss and stopped me. "What?" I asked in confusion, "Is something wrong?"

"No no no," she replied, "I'm still sore from last night, you weren't exactly gentle."

"Oh," I said with a certain amount of relief and worry at the same time. I was satisfied that my cock was big enough to leave her sore the day after but pissed that I couldn't fuck her perfect ass again.

My worry was instantly erased seconds later when she replied, "This morning it's your turn, I'm doing all the work." Before I had a chance to say anything she spun me around and pushed me up against the breakfast table. She instantly pushed her body up against my back, at the same time she reached around my waist and starting groping at my package. My cock had been rock hard the second she walked in the kitchen and she quickly went to work on my raging member. Through my khaki shorts she slowly pumped up and down my shaft. At the same time she began grinding her groin up against my ass. I could feel her hardening cock push against my ass. Even though we'd just started I wasn't sure I could last much longer. I could feel her package grinding against my eager ass, I wanted her badly and she noticed my moans. Every time she slowly pushed her groin against me I let out a soft moan. She observed my pleasure and began grinding against me with more and more haste. I began moaning louder and louder and as I nearly reached my limit Katie began to slow her thrusting down. "We can't have you cumming before I even get your cock out of your shorts now can we?" she whispered into my ear.

Undoing the button on my shorts and unzipping my fly Katie was finally about to releasing my raging dick. Once unzipped, she slowly pulled my boxers and shorts down, exposing my bare ass to her groin. She gave my ass a quick thrust and I felt the cotton of her thong push up against my asshole. The sensation of panties brushing over my sphincter caused a chill to crawl up my spine. I then felt Katie's lips slowly push against my mid back. She began tracing her way up and down my spine, planting small kisses along the way. After about a minute her kisses began heading towards the crack of my ass. Still bent over the table, her mouth had easy access to my waiting asshole. Her lips ran up and down the crack of my ass, between my asshole and lower back. She teased me for what seemed like eternity. She finally got down and her knees and fully spread my cheeks. Just as I was about to explode with anticipation she dove towards my asshole. She wasn't teasing anymore as her tongue furiously flicked across my tight ass. Her hands grabbed at my ass cheeks as she continued to spread them apart for easy access. I spread my feet farther apart to help her access my asshole even easier, I was so eager for her to service me. Her tongue felt like hot fire as it grazed across my tight hole. I moaned in delight as she began to thrust her tongue against my hole. With every thrust of her tongue my hole loosened more and more, slowly becoming used to its new intruder. As my hole relaxed Katie began fucking my hole with her tongue. She continued to thrust her tongue in and out of my ass as my moans grew louder and louder.

"If you don't calm down a little you aren't going to hold your load 5 minutes into this thing," she said as she continued to service my ass. I didn't care about holding my load anymore, I was past caring, I was in complete ecstasy. After what seemed like eternity her mouth broke from my asshole and stood up behind me and turned me to face her. Before I had a chance to do anything she pushed me down onto my knees, my face staring straight at her bulging black thong. I knew instantly what she wanted and began to kiss around her package, teasing her as she had teased me. She quivered in delight as my lips slowly traced around her package. Her panties were slightly see-through and I could see her cock desperately trying to break from her restrictive thong. With one hand I began caressing her bulging thong and with the other I reached around and began grabbing at her ass. Still teasing my lips around her package I could hear her moans grow louder and louder. After a bit more teasing I finally replaced my hand with my mouth and began kissing her package. Her cock was so hard I could nearly suck up and down her shaft through her cotton thong. Not wanting her cock to suffer any longer I finally released it from her panties.

I slowly pulled her thong aside and exposed her long shaft. Her cock seemed even harder now than it had the night before as it easily stretched 7 inches. Katie was still a bit thinner than Michelle's massive tool but not by much. Deciding not to tease her anymore I drove her cock into my waiting mouth. With one hand on the base of her shaft I slowly began sucking back and fourth on her long cock. I couldn't even take half her cock into my mouth but she seemed to be enjoying herself none the less. I barley had an opportunity to suck her cock on my own before Katie began slowly thrusting back and forth into my mouth. I felt her hands reach down and lightly grab either side of my head as she began fucking my mouth faster and faster. I had little control over the situation while she pumped her cock into my mouth, moaning louder with every thrust. Still on both knees in front of Katie I could feel her cock slamming against the back of my throat over and over again. Oddly enough my gag reflex was relaxed and I allowed her to pump in and out my mouth as she pleased.

"Warm your tight little ass up for me," she instructed between moans. I was pretty sure what she wanted me to do but I was nonetheless a bit hesitant. I had never gone anywhere near my own ass, I'd always allowed my partner control over that area. Not wanting to dampen her mood however I reached one of my hands up to her mouth. She opened for my approaching hand and coated my fingers in her own saliva. Now that I had some form of lube I reached down between my thighs and searched for my hole. I wasted no time, thrusting my middle finger past my sphincter with one fluid motion. Katie had slowed her thrusting, presumably to watch me as I followed her instructions, pleasuring my ass for her. I let out a soft, muffled moan as my finger slid deep into my ass. Her cock still buried deep in my mouth made any noised coming from my mouth nearly inaudible.

"Oh yea that's it, work your little ass for me," she moaned, only encouraging me to give my ass more attention. I began thrusting my middle finger in and out of my eager asshole. She continued pumping her cock in and out of my mouth but she leaned to the side a bit, obviously trying to catch a glimpse of the attention I was giving my ass for her. Shortly after my middle finger found the inside of my ass, my ring finger followed. I let out another loud moan as my two fingers now stretched my asshole so a size closer to that of Katie's cock. I looked up at her and she gave me a broad smile of approval as I began working both fingers in and out of myself. It was an odd feeling, very different from begin fingered by your partner. There wasn't the feeling that something foreign was being stuffed in your ass, it was a more welcoming feeling, like my ass knew exactly what it was being filled with. As my ass became more and more accustomed to my fingers I began slowly fucking my own ass. Katie could see my arm moving faster and faster against my ass and I could tell she was loving it.

"That looks so hot, are you almost ready for me baby? Have you given your ass a long enough working?" She questioned me. I nodded yes to her and she finally withdrew her saliva coated cock from my mouth. I followed suite, withdrawing my fingers from my ass with a pop. She pulled me up towards her face and planted a short but furious kiss on me. "Wait right here," she instructed. She ran back towards her room and was back in the kitchen in less than 10 seconds. I couldn't help but stare as she ran towards me, her massive tool bouncing up and down in unison with her large tits. She didn't say anything; once she got near me she turned me around and pushed me down towards the table. I was now hunched over the side of the table, Katie standing directly behind me, her massive tool point strait at my quivering asshole. My ass seemed to know that it was about to be abused by Katie's massive tool. I looked back towards her to notice the bottle of lube that she grabbed from her bedroom. She began coating her long cock in lube, using her hand to rub it in. My dick began to grow again as I watched her stroke her member as she covered every inch of her tool in lube. When Katie was done with her cock she squirted a generous amount of lube onto two of her fingers and used them to apply the glob to my waiting asshole. Now that I was finally ready for her to enter me I felt my stomach twist again; I'd wanted her inside me for what seemed like hours and she was finally about the grant my wish.

My ass jumped as I felt Katie's tool push up against my sphincter for the first time. I looked back over my shoulder to watch her as she guided her cock into my waiting ass. One hand on my ass, the other on the base of her cock, she stared down at my hole as she guided herself into me. My sphincter did its best to resist her cock, denying her entrance to my quivering asshole. She pushed harder against my hole, fighting the constraint of my sphincter; she knew it would eventually give way. After a bit more pressure her cock finally popped inside of me. Within half a second 3 inches of her cock was buried into my ass. I always loved the first few seconds of penetration; it certainly hurt like hell but at the same time it felt so good to feel your ass being filled by a fat cock. I let out a long moan the second Katie popped into me, I could do nothing put grip the table as hard as I could, waiting for the initial pain to pass. Katie let her pole rest inside my ass for a minute or two until I was finally accustomed to her.

When the pain finally began to subside I reached back and grabbed her ass. Pulling her towards me, her cock slowly buried itself deeper and deeper into my ass. I continued to pull her towards me until I finally felt her groin against my ass. Katie then began slowly pumping in and out of me. She slowly pulled her cock almost all the way; I felt my sphincter strangling the head of her cock. Just as her cock was about to pop out of my ass Katie thrusted it back into me. My knuckles were completely white as I gripped the edge of the table with all my might. Katie was now quickening her pace as she continued to fuck me from behind. With both her hands on my hips, Katie slammed her cock deep into my ass over and over again. Turning my head back around, I watched Katie as she pummeled my ass. Her tits were bouncing all over the place as she slammed herself into me. Her eyes were staring down at her cock, she was completely concentrated on servicing my asshole. She looked amazing in her garter and stockings, so incredibly feminine. She reminded me of secretary that was fucking her naughty boss. She finally caught me staring at her and gave me a smile and a wink.

Katie was even better at holding her load than me; she never slowed her pace as she slammed her cock in and out of me. My moans grew louder and louder with every thrust, at this point I didn't care if any of the neighbors heard. I was in complete ecstasy as Katie continued to pummel my ass. The slapping of her groin up against my ass was nearly as loud as my moans. Katie was now fucking me as hard as she could. Her groin slammed up against my ass over and over again and she fucked me with all the energy she could find. I glanced back and saw my ass cheeks try to absorb the force of her thrusts. Without even touching my cock I felt myself becoming closer and closer to cumming. Never before had my cock become this excited without any attention. Just as I felt myself seconds from cumming Katie slowed her pace and withdrew from my ass.

Before I could ask her why she had stopped Katie had grabbed my hand and guided me out of the kitchen. As I followed her through the hallway my eyes found her gorgeous ass, bouncing back and forth with every step she took. She still had her black thong on and it only accentuated her ass even more. When we finally reached the bedroom Katie pulled me towards her and began kissing me. She buried her tongue deep in my throat as she groped my ass. Not 10 seconds after she started our kiss she was pushing me down onto the bed. I laid down onto my back and Katie lowered herself down between my legs. I noticed the bottle of lube in her hand as she began coating her cock in lube all over again. Once her massive cock was properly lubed she grabbed both my ankles and pushed them up into the air, exposing my ass to her massive tool. As she began pushing forward I reached down and guided her cock towards my hole. Katie's cock was rock hard and felt as wide as cucumber. I had no idea how my ass was able to handle her girth but I guided her back into me once again.

Katie's cock thrusted past my sphincter for the second time that night and I let out another long moan as she entered me, this one even louder than the first. She wasted no time the second time around as Katie instantly began pummeling my sore hole. Katie began to lean down towards me, pushing my legs up against me chest, exposing my ass even more to her massive cock. With both hands on her ass I helped her slam her cock into my ass with fury. Katie was now staring into my eyes as she filled my ass to the brim. I stared right back at her while moaning on top of my lungs. I was now almost past simple moaning, nearly elevated to screaming while Katie's relentless cock fucked me.

I quickly felt myself nearing orgasm once again. Taking one hand off her ass, I began jerking myself off as Katie fucked my hole. Mere seconds after I started jacking my cock I felt my orgasm building. My moaning became even loader and Katie continued to quicken her pace.

"Ohhhhh cum for me baby," Katie moaned through clenched teeth. I didn't need anymore instruction than this and instantly began shooting my load all over my chest. I could feel my prostate swell as I shot glob after glob of cum onto my stomach. My swollen prostate only heightened the sensitivity of my ass as Katie continued to bury her cock in and out of me. I was screaming louder than I ever had before, far past mere moaning, this was full blow yelling. It had been by far the most intense orgasm I'd ever felt and I got the feeling that Katie knew it too. As I finally stopped cumming Katie slowed her thrusts and leaned down to kiss me again. "So I guess that was pretty intense for you?" she asked with a smile on her face.

"That was absolutely amazing," I replied.

"Your little ass is just so tight I knew you would love it," she said. With Katie's cock still buried in my ass we finished our kiss and she finally withdrew from me. I rolled out of bed and headed for the bathroom, cleaning myself off when I reached the first towel I saw. Once I'd finally cleaned the massive load off my chest I headed back for the bedroom. Katie was now sitting against the headboard her back upright and her legs straight forward, and her pulsing tool still sticking straight up in the air. I knew she wanted more and I was ready to give it to her. Grabbing the lube in one hand I mounted her, moving both my legs to either side of her. I reached back around and squirted some lube on her cock. Once she was properly lubed I began lowering myself down onto her tool. This time her cock pushed pass my sphincter with barley any resistance. The head of her cock pushed deep inside my ass once again as I began riding her cock. Katie placed both her hands on my asscheeks and began moaning softly as I serviced her cock with my ass.

For the first time that night I was servicing her. I did all the work as I began quickening my pace. I bounced up and down on her cock with fury now and I could hear her moans quicken. The bed began to creek as I slammed myself up and down on Katie's member. "Oh ya that's the spot, don't stop, don't stop," she moaned as she stared into my eyes. Following her orders I rode her cock the best I could, trying to keep my speed up. Her moans began getting louder and louder and I knew she was nearing her climax. "Oh yea John that's so good baby, can I cum in your ass?" she asked through moans. She caught me off guard for a second but deep down inside I knew I'd always wanted to know what it felt like to have a hot load shot in my ass.

"Ya baby you can cum in my ass," I replied as I continued to work my hole up and down her cock. Only a few seconds later her moaning quickened and I could feel her cock swelling inside my ass.

12
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • High School Friend Has A Secret Ch. 03

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 17 milliseconds