My Best Friend’s Older Sister (Part 2)

My Best Friend’s Older Sister: Part 2

I was in the deep end of the pool, well away from the edges, but I wasn’t afraid. Even though I didn’t know how to swim, I seemed to be treading water pretty well.

Trill, Trill.

What was that? I looked around, water lapping at my face, but couldn’t find the source of the noise.

Trill, Trill.

Something seemed to grab my feet and I started to sink a little bit. Still not afraid, I let it happen, with the knowledge that being over my head was not necessarily a bad place to be…

Trill, Trill.

“Wake up, sleepy head.” Maddie’s sultry voice whispered in my ear. Through the crack in my eyelids I could see her turning her phone alarm off and resetting it. “You’ve had an hour to rest, now it’s time for you to please me again.”

A flood of memories came rushing back. My night with Maddie hadn’t been a dream, it had really happened. My dream girl was no longer only a dream.

“You’ve got dried sweat, drool, and cum all over your face. How about we take a quick shower and then start round two?” She purred into my ear.

“What time is it?” Was the only thing I could think to say.

“Two a.m.” she said. “I set my timer for an hour after you passed out. I figured you needed a little sleep to recharge.”

I tried to put my arms around her but found that my wrists were still tied to the foot posts of the bed. I grunted in frustration, causing her to giggle.

“I left you tied to help you remember Rule #1. By the end of the week, I’m hoping it’s no longer necessary, but for the rest of tonight, don’t expect to have much freedom of motion.” She kissed the tip of my nose. Quite possibly the only clean part of my face. “Don’t go anywhere” she giggled, knowing I was tied up. She got out of bed and rooted through her suitcase, pulling out a few items and taking them into the bathroom. She ran the faucet for a while and returned with a clear plastic bottle that had a tapered straw built into the top. It held no more than a cup of fluid. She put it on the nightstand and untied my wrists. Her soft cock swinging near my face as she did so, making me horny and my penis’s attempted erection reminding me that it was securely locked in her pink Holy Trainer. My arms were sore from being held up and away from my body for so long. I had to massage the muscles and flex the joints to help the stiffness disappear.

“The bottle is an enema for you to clean yourself out. First, go to the bathroom and take a shit. When you’re done, insert the nozzle and squeeze the contents into your rectum. Hold onto the water inside you while you wash and refill the enema in the sink. The go back to the toilet, let the water go, and when you’re empty, reinsert and cleanse again.” She handed me the bottle of silicon lube as well. “Just use a drop per insertion, that’s all you need.”

“You’ll probably need to flush five or six times to make sure your colon is completely clean. If the expelled water is anything except clear, keep repeating the process. I’m going to finish unpacking while you’re cleansing yourself for me.”

I did as she instructed and it took eight flushes to make sure I was totally clean. The time in the bathroom also gave me a chance to finally look at the chastity device that was locked over my penis. The two pieces interconnected pieces fit me so well it was as if they had been built specifically for me. The ring was ergonomically molded. It was surprisingly comfortable around my scrotum and over the base of my shaft. The tube that housed my penis was silky smooth in texture yet unyielding to any attempt to give stimulation. When I was in 8th grade, I had broken my wrist and the chastity device reminded me of the cast that was on my arm. I absolutely couldn’t feel anything on the other side.

Washing up after my cleansing, I saw what Maddie meant about the dried drool and cum on my face. I had faint white streaks all over my lower face from drooling through the ring gag and a couple of thicker spots of white that must have been Maddie’s left over cum. I washed my face clean and dried it with a fresh hand towel. Then I folded the towel, leaving it at the corner of the counter along with the washed and emptied enema bottle and the lube bottle.

I left the bathroom and saw Maddie on laying spread out on the bed. She had taken off her lace teddy and was completely nude and unbelievable gorgeous. She had no hair on her body, except for her head. Her taut, muscled body looked like it belonged to a professional trainer. Her face looked like it belonged to a Greek Goddess. Her perfect breasts looked like Michelangelo had painted them on her. And her semi-erect cock was already at seven inches and slowly growing. I hadn’t had a good view of it in the light before, but from prior experience, I was certain it would get to about eleven inches when she was fully excited.

“Oh you look much better.” Her wicked smile made a quick return and her fingertips went up to fondle her nipples. “I think a little blow before we shower is a good idea, don’t you Sweetie?”

Once again, I lost my voice and could only nod. I don’t remember how I crossed the thirty feet from the bathroom door to the bed—I only remember sliding her growing monster into my mouth and down my throat in one smooth movement. My nose rested against her pelvis once again, as I now knew that’s where it belonged.

“Ooooo-ahhhh.” She said. “Damn, you’re good.” She paused to catch her breath, “I’ve only had one other that could deep throat me, but with her, it was always a struggle to keep her from choking.”

I slowly pulled her now nine-inch member from my mouth and looked Maddie in the eyes, “Her?” I asked, then took her deep once again.

“Mmmm.” Again, she needed a moment before she continued. “I’m more attracted to boys than girls, but last semester, my dorm-mate must have caught wise that I’m trans and surprised me one night by giving me a blowjob while I was asleep.” She give a little laugh, remembering the scenario. “It was the Sunday night after the first week of class. It was late and dark and we didn’t talk, but I knew she knew I was awake. It didn’t stop her from making a valiant effort though. After a few minutes of just using her mouth, she tried deep throating me, but gaged me back up. I could tell she wanted more, but when she tried to keep it deep, she would choke me back up.” Maddie moved her hands from her breasts to the sides of my face, helping to guide my head up and down on her still growing shaft. “Finally, I had to take control—just like this.” She squeezed her fingers, indicating that she had held her dorm-mate’s head in the same fashion. “And I fucked her face like she wanted…” As she took control of me and jammed my head up and down on her now fully engorged cock. Each stroke forced her cock down my throat. I got into the same breathing method as before, in breath on one stroke, out breath on the next.

I had thought this was just going to be foreplay, but she keep up her motions, running my mouth down to her pelvic bone for more than ten minutes. Her grunting and pumping started getting even more vigorous and I knew she was getting close. “Get ready to drink my cum, Sweetie.” She said between her jagged breaths and I mumbled back my willingness to accept her liquid gift. She jammed my face hard against her pelvis and bucked her hips as she deposited stream after stream of cum deep into my throat. My need for air started as an itch but quickly become immediate. I fought the urge to pull off her beautiful cock and within moments she release my head and I slid off her member, panting for breath.

She sighed deeply, then continued her story. “When I had finished giving her my load—like how you took mine just now—I sighed, rolled over, and pretended I went back to sleep. I didn’t say anything or even acknowledge what she had done. She went back to her bed and I could hear her masturbate herself to sleep.” She paused to look me in the eyes with her supermodel smile before continuing, “The next day she never mentioned anything about it. We continued the facade that nothing happened until the following Sunday night, when she came to my bed and did it again. The only difference the second time was when I had given her my cum, she whispered, ‘Thank you,” before she retreated back to her bed and frigged herself until she passed out.”

Maddie reached down and touched my cheek which was resting on her thigh. “That continued the rest of the semester. It was always on a Sunday night and she would wait until she thought I was asleep. Then she would blow me to completion, thank me, then frig herself to unconsciousness.” She blew me a kiss. “I think she was a virgin. She ended up getting engaged over the Christmas holiday and moved out before the next semester started. I think she was using me as practice for her soon-to-be fiancé. Not that I mind, two-birds with one-stone and all, but I did miss the deep throating… until you came along, Sweetie.”

She rolled around on the bed and came up face to face with me. She give me a quick, but deep kiss then jumped from the bed with her still erect monster bobbing between her legs, “Time to shower.”

Maddie adjusted the twin shower heads to the temperature she preferred. It was a little on the hot side for me, but not uncomfortably so. She put her head under the bigger of the two heads and started wetting the mane on her gorgeous head. She picked up the bar of soap and handed it to me, “Wash my back, Sweetie.” I lathered up and followed her instructions as she worked a liberal amount of shampoo into her hair. She turned around to face me, her eyes closed against getting shampoo into them, “And my front.” I happily complied again. The Holy Trainer effectively keeping my excitement contained. “Mmmm…” she hummed, “A little more attention on my nipples, please.” I carefully made sure her pert, perfect nipples were absolutely clean. “Good. Now my cock. It’s been in some dirty places—make sure you do a good job down there too.” My breathing quickened a bit as I felt her massive erection in my hands. Her cock was easily four times the volume of mine when fully aroused. I could just barely wrap my hand around her girth, touching the tip of my middle finger to the tip of my thumb. Covered in foam and lather, I started to slowly jack her off and she she moaned in pleasure. I was about to put more soap on her when she turned around and let the water wash the soap from her front.

“Sweetie, wash my bottom too.” Soaping up, I rubbed my hands along her cheeks and down her crack. I repeated the process again a little slower, rubbing my fingers in the flesh of her buttocks. She arched her back and bent forward a bit, rinsing her hair and saying, “My anus. Don’t forget to clean my pretty little anus.” I didn’t need to be told twice. I carefully ran a soapy finger up and down along her pink puckered flesh. I was swiftly rewarded with a moan of pleasure. I started to make little circles around the outside and teased her entry.

“Madeline, may I clean you on the inside as well?” I asked.

“Mmmm… yes, but not with your finger.” She turned to rinse the soap from her rear and then spun to put it back in front of me, “Use your tongue, my Sweet.”

My penis twitched uncontrollably in its pink sheath as I knelt down and buried my face in her crack. I attacked her ass with my tongue and forced my way through her sphincter. It was depraved, yet I couldn’t get enough. A day ago I would have never thought of doing this to another human being. Now I couldn’t get enough of pleasing the Goddess in front of me.

“Yes. Fuck my ass with your tongue.” She pushed back on my face, making my tongue penetrate her deeper and deeper with each push.

After a few minutes she stood straight up and turned around. She put her hands under my arms and lifted me to a stand. She wrapped her arms around me and kissed me deeply. “That was very nice.” She said between her deep kisses. She nodded toward the vanity and said, “Get the lube, my Sweet.” As I exited the shower, dripping all over the floor of the bathroom. She started applying conditioner to her hair, “Hold on a moment.” She said as she massaged it into her locks. “I like to let the conditioner stay in for a while, so we’ll occupy ourselves another way while it does its job.” Rinsing her hands, she took the lube bottle from me and put a few drops onto her massive hardon. She motioned for me to turn around and then put a free hand on my back to get me to bend over a bit, “Good boy.” She said when I did. I could feel her slippery finger spreading lube around my ass and the surrounding flesh. I heard the flip lid of the bottle close and felt a slight pressure on my anus. “Since you’re clean inside, we won’t need a condom. I get to feel the real you this time.” She pushed a little harder but not hard enough to enter me yet. “I’m very excited to feel your flesh on mine.”

I groaned in anticipation. “Me too.”

With a little more pressure, the head of her cock popped completely into my ass. “Ooh, that’s good.” She said and held me there for a moment. “Jacob Dear, don’t forget that when I get ready to cum, it will be in your mouth.”

“I can’t wait.” Was my reply.

“I’ll let you know when I get close, then I want you to spin around and deep throat me in one gulp. Can you do that for me Sweetie? Can you take my cock directly from your ass and into your throat?”

I shivered at anticipation at the thought, but quickly answered honestly, “Yes. Yes I can.” As soon as I said it, she impaled me to her hips. I cried out in complete surprise, a little pain, and a lot of pleasure. My right hand instinctively went to my crotch to jack my penis, but it only found plastic. Thwarted, I put both hands on the shower wall ahead of me and let her pound her naked cock into my only available sex organ.

“Mmmmm. That feels much better without a condom, don’t you think so?” I tried to answer, but between her pounding thrusts, all I could muster was a series of grunts that could have meant anything. “I’ve cum so much the last few hours… to get another load out of me may take a while.” She teased me and I responded with another round of positive sounding grunts.

Her hands rolled over my hips so she could get a better grip on me. With the increased leverage, she was able to pound into me harder, deeper, and with less effort. It also changed her angle a bit and I could feel the tip of her cock vigorously plowing directly into and across my prostate. I could tell her conscious mind was fading away as she was calling out, “Yes,” “Fuck,” and “Ass,” with each powerful thrust into me.

My conscious mind must have been fading as well, because I was replying back, “Harder,” “More,” and “Fuck me,” without even realizing it. This continued for what felt like an hour, both of us lost in the pleasure of our physical carnal act, when all of a sudden I felt like I had to pee. I had to pee really bad. It made me start to clench my anus tightly around her thrusting meat.

“Maddie…” thrust, “I have to…” thrust, “pee…” I was barely able to squeak out. My knees were getting weak as I was panting due to this new form of sexual distress that was unknown to me.

“That’s a…” thrust, “prostate…” thrust, “orgasm…” Her pounding got even harder. “I’m…” thrust, “going to…” thrust, “fuck the…” thrust, “cum out of you!”

Knowing that something exciting was about to happen made me even more horny for her rock hard cock to keep penetrate me. I felt the urgent need for more pressure on my prostate, so I arched my back and rolled my hips a bit more. The result was immediate. Her next thrust smashed directly against my prostate and made me feel like my bladder had let go, but without urine actually coming out. “Ahhhhh…” I cried as my legs went rubbery. I would have fallen if Maddie didn’t have a solid hold on my hips. Something warm and pleasant was going on with my penis, but I couldn’t tell what. I looked down between my legs, and a thin stream of white semen slowly seeped out of the opening of the Holy Trainer. “Ahhhh…” I continued, uncontrollably.

The slow seeping seemed to go on and on, never ending. It wasn’t the type of orgasm I was used to, but it was a pleasurable release in a different way. A deep soul-cleaning release that made my whole body tingle. And it didn’t stop! Unlike a normal orgasm, where the crescendo last for a few seconds, this kept going as long as Maddie kept pounding my prostate. I secretly wished she would never stop—that she could hold off cumming for at least another week. I was in a blissful state that I’ve never ever experienced before and didn’t ever want to end.

“Ahhhh…” I continued to moan. Time had no meaning and the most amazing sexual experience of my life continued as my semen collected on my right thigh. I heard Maddie huff, “I’m close… get ready… get ready to throat me!” Gripping my hips and pulling my ass off her massive dick, she spun me around and grabbed me with one hand behind my neck and the other on top of my head. I was barely able to get my mouth open before her cock head was touching my lips. In a single swift motion, she forced herself down my throat until my nose smashed against her pelvic bone. She jerked twice and then unloaded her sticky cum into my hungry stomach.

I was still in the bliss of my prostate-induced orgasm and must have passed out from lack of oxygen with her cock pulsing her cum down my throat. I awoke on shower floor, her pulsing member pulled from my throat but still resting in my mouth. She was at the end of her orgasmic climax and all that was left were a few drippings that dribbled out with her final contractions. She finished by using a finger to milk the last of her cum out of her urethra from the base of her member to the tip. Of course, I greedily accepted it all. The knowledge that this beautiful cock had just been in ass just moments before I swallowed it was intoxicating. As my own orgasm subsided, I started to suck on the monster dick that lay in my mouth, hoping her erection wouldn’t subside and that she could give me more of what I wanted. More of what my prostate needed.

“Jacob, Darling,” she patted my cheek, “You really are a cum slut, aren’t you.”

I replied by gripping the base of her member with both hands and jacking her off in my mouth while my tongue traced circles over that wonderful crown of her beautiful penis.

“Okay, okay…” she said, making a long exhale. “That’s just a little too much… give me a minute.” She moved to pull out of my mouth, but left my hands wrapped around her girth. “Whew.” She breathed, “That was more than I expected for your second time.” She started to get up and helped me up as well. “I’ve only had one other lover who was able to have a p-gasm, and we had to fuck two dozen times before he was relaxed enough to have it.”

She reached down between my legs and scooped up a mix of semen and pre-cum that had exited the Holy Trainer and was stuck to my leg. Mixed with a little runoff shower water, the scoop entirely filled her cupped palm. “Open up Sweetie.” She said and I did. She fed the mix of my own making to me and I gulped it down. “How was your first sissygasm? I think you really liked it.”

“It was amazing… sissygasm? You don’t think I’m a sissy, do you?” I was concerned she wanted to dress me as a girl and parade me around. I knew that I loved her girl-cock, but it didn’t mean I wanted to be a sissy.

“Of course not. It’s just another name for a prostate orgasm. A way for you to obtain sexual pleasure and satisfaction without direct stimulation to your penis.” She dug her pinky into the open slit at the tip of the Holy Trainer, collecting two more drops of my concentrated cum on her fingertip. “Since you appear to be able to have them so easily, there’s no reason to ever remove your chastity device, what do you think?” She placed her fingertip in my mouth and I greedily sucked the last of the cum from it. The taste of cum was rapidly becoming a necessity to me.

“Mmm hmm.” I hummed enjoying the cum. But I think she took it as my answer to her question… which was probably okay with me as well.

“Good. Actually, it’s great! While we’re in Bangkok, let’s look at some more secure chastity options to make sure you can only find satisfaction with my cock deep in your ass—all the more sissygasms for you, and all the more boi pussy for me!”

More Secure, I thought, wondering what that would be. However, did it really matter? I told her what I was thinking at that particular moment, “Madeline, as long as you can make me feel like that again, any chastity device you want to put on me is just fine.”

“I knew you would agree… though it’s not like you really have much of a choice.” Her wicked smile returned again. I was starting both love and be afraid of that smile, but it was certainly beautiful. Realizing my fate for the week, I felt a warm tingle feeling of being owned by such an amazingly beautiful and sexually aggressive woman.

“For as long as you’re with me, you’ll be locked in chastity. No ifs, ands, or buts.” Her tone serious, as if she were dictating the terms of a contract, which is what it felt like she was doing. “Do you understand? Do you agree to this condition?”

“I do.” I whisper back, feeling like it was a vow.

She smiled her radiant, heart warming smile at me and then nodded to the still running shower heads. “I need to get this conditioner out of my hair and let’s get cleaned up before our next round.”

We did and she left her hair wrapped in a towel as we got between the sheets. It was the only thing she was wearing and the pink Holy Trainer was the only thing I was wearing. She set her phone to wake us again at 5:00am, giving us just under two hours of much needed sleep before she would wake and ram her monster phallus into my hungry orifices again. She lay on her back in the middle of the king-sized bed, demonstrating that it was hers, not mine. She motioned for me to snuggle with her, to rest my head on her shoulder as she wrapped her arm around me. She had me on my side and guided my hand to hold her warm, soft, deflated member. “Just hold it as we sleep.” She said. It was much larger than an average flaccid penis, probably just over five inches long and an inch and a half in diameter.

“How do you hide it?” I asked. “I mean, when you wear tight jeans and skirts?”

She laughed, “Very carefully.” She slid her legs apart a few inches and reached down to her groin. She stretched the soft flesh down toward her toes and then pushed it underneath her, seating her flaccid cock between the globes of her buttocks. I could feel that her testies were separated to each side of her shaft and could imagine that they look would look like her labia, when she had panties on. “I use body tape to keep it in place and to cover the head so I don’t get too excited by the friction of walking around. You’ve seen me with tight jeans on… what did you think was under there?”

“Uhh.. I always thought you had a pussy.”

“Worked pretty well then, didn’t it?” She asked rhetorically. “The bigger problem is that I’m always horny, something about the testosterone levels I produce are significantly higher than most women.” She must have felt my alarm, as she giggled in response, “Don’t worry, my estrogen levels are even higher, so I’m not going to start growing a mustache or get male pattern baldness.” I relaxed again against her, and she let her member out from it’s trappings, placing my hand back on it. “As you can imagine, when I get too horny during the day, a little bit of body tape isn’t going to hold back this python.”

She yawned, but continued. Her voice was softer and slower and I knew she was tired, but she wanted me to know this part of her story. “I was lucky in high school. You remember Todd? My boyfriend when I was a sophomore?” I nodded, my nose rubbing agains the side of her breast, “He was a senior at the time and since we were both honor students, we got the period before lunch for remote access AP studies. Todd and I were the only honor students to choose math for AP, so we got a small class to ourselves and would remote into the University’s lecture hall for calculus class. At first, he would only blow me during our daily time together, but he finally worked up the courage to let me take his virginity and to routinely fuck his ass.

“It worked out better that way, since it turns out that calculus is hard, and when he would blow me, he would miss most of the lecture. When we moved to fucking, I would take him from behind, so we could both watch the lecture and at least get the gist of what was going on—even while my dick was a foot up his ass.” She turned to me for a moment, “He was the one that took over a month to have his first sissygasm. The trick, as it turned out, was to deny him regular orgasms, which is how we found chastity play. It was a game changer for both him and for me.” She kissed my forehead, “And now I won’t play without it.”

She took a deep breath and continued, “But school ended, and his parents insisted he go to the same private college they went to, so now he’s at Pepperdine. We don’t keep in touch, but it’s likely living a bi lifestyle. He’s into women, but like you, he’s also a huge cum slut.” I felt her kiss my forehead again. “My first week as a junior was a problem, since I didn’t have a good way to sate my desires during the day. I doubt you’ve ever been in a high school girls’ bathroom, but there’s not much privacy to jack off in a stall. It got so bad that first week, that I went to the school nurse and asked if she had anything to tamp down a hyperactive sex drive. I didn’t realize it, but I was showing under my skirt. Nurse Nguyen took a seat beside me on that ugly yellow vinyl couch in nurse’s office. She started to talk me through my sexual desire problems, but I told her that I just needed some kind of anti-horny medication and I would be fine. That’s when she rested her hand on my half-hard cock poking out from under my skirt. I froze, never having been exposed before, and not knowing what to do. Nurse Nguyen started rubbing me, right there in the nurse’s office! She gently pushed me over and had me lay down as she gave me the most unexpected blow job of my life.” She paused to laugh at the unbelievability of the situation. “One thing led to another, and my remote AP courses for Junior and Senior year ended up being organic biology, hosted by Nurse Nguyen. She never let me have her ass, but between her skilled mouth and her shaved pussy, she was able to give me the daily draining I needed.”

“College has been much easier. It turns out there’s an endless supply of college-boy bottoms that advertise on anonymous hook up sites. They set themselves up in dark rooms, pre-lubed, ass-up, and blindfolded. It took me a while to find my favorites, but I’ve got ‘Tom’ on Tuesdays and Thursdays, and ‘Wendell’ on Wednesdays and Fridays. I go through a lot more condoms, but in case you haven’t noticed, my family is rich—so buying rubbers by the gross isn’t much of a problem.”

“‘Tom’ and “Wendell?’” I asked?

She giggled, “That what I call them. You don’t need to worry about competition—they really are just cum buckets for me. A means to an end to cull my daily urges. I call my Tuesday and Thursday appointment ‘Tom’ because the name and the days start with a ‘T.’ All I really know about him is that he’s a skinny, soft femboi that weighs maybe 120 pounds. Wendell, ‘W,’ is a redshirt freshman basketball player. He can’t get what he wants in public for obvious reasons, so I give it to him in private—from behind—in the dark.” She turned her head to me and whispered, “He thinks I’m a guy. It’s actually hilarious.”

“Okay, enough stories. We have more to discuss, but let’s get some sleep first.” I nodded against her breast and she said, “Good night, Sweetie.”

* * *

I woke up with an urgent need to empty my bladder. We were in the same position as when we fell asleep, so I had to carefully untangle myself without waking Maddie up. My hand had still been on her lovely, prostate-orgasm inducing cock. But unlike the softness of when we fell asleep, she was in the middle of her morning woody. Half walking and half running to the bathroom I stood in front of the john and realized that I wouldn’t be able to aim very will with the pink Holy Trainer locked on me. Not having the time to figure out a better method, I lowered the seat and sat down to pee. The feeling of relief over then next fifty-two seconds was wonderful. Looking at the clock, I noticed it was 10 minutes until 5:00am.

In the mirror, I saw a naughty little smile cross my lips as I stood and took the enema kit and cleaned myself out again. I must have done a thorough job last time as it only took three flushes until my colon was ejecting crystal clear water. The clock now read five minutes to 5:00am. I grabbed the still full bottle of lube from the shower and took it back to the bed. First, I moved her phone from the night stand to nearby her right hand—so she should be able to reach it when she woke. Then, very quietly, I applied a few drops around my anus and the surrounding flesh. I then carefully pulled back the sheet from Maddie’s sleeping form and slowly but carefully applied drops of silicon lube to her rock hard cock. I put a few extra drops on the head and then put the bottle on the nightstand. Very carefully, I straddled her hips without touching her, I hovered over her, not wanting inadvertent contact to wake her. Then I slowly lifted her massive, eleven-inch long dick by the base, holding it straight up—pointing it directly at my quivering asshole. Hovering there, I waited for the alarm to sound.

Trill, Trill. Her phone sounded and I took the plunge, dropping straight down to her hips. Unexpectedly, all the air came out of my lungs. In two short hours, I had forgotten how much larger she was than my colon seemed to have space for. Her eyes flew open as I lost balance and started to fall forward. She reached up and held me in place with her hands on my shoulders. At that moment, I was aware of two things: making short, panting breaths; and an all-encompassing feeling of fullness in the pleasure center deep within my loins.

Trill, Trill.

Maddie started bucking her massive cock deep into my body. Pushing the breath out of me with each thrust. She was deeper in me than ever before and I was paralyzed by the sensation. What had seemed like a good idea moments ago now seemed like a recipe for my own abuse. I wasn’t in pain, per se, but I was completely overwhelmed by the enormity of her presence within my body. I was unable to move, think, or apparently breath.

“Oh you naughty slut.” She said as she continued to buck her hips, thrusting deep enough into me to compress my lungs.

“Ughh.” I panted, over and over as the head of her rock hard cock deflected my diaphragm. She pushed me into a sitting position and I was temporarily able to keep my balance, my arms dangling uselessly at my sides.

Trill… I heard the phone stop making noise and somewhere in my head realized that she much have turned the alarm off. My battle with keeping my balance ended in failure and I collapsed backwards, but not before she reach out to my thighs and held my lower body in place. As she was becoming more and more awake, her bucking thrusts became deeper and harder. From this new angle, where my torso had fallen on top of and parallel to her legs, I could feel her cock distending my lower abdomen. The shift in assault gave me the chance to breath somewhat normally again, but my body was still like a rag doll due to the intensity of physical intrusion I was undergoing. I could feel my anus start to spasm. Grabbing and releasing Maddie’s cock multiple times a second.

“Yes!” She hissed, pleased at the reaction my body was giving her endless assault. “Give me that assgasm.” Impossibly, she was bucking me even harder, “Milk my cock with that pulsating anus.” She was using her hands to pull an push me in conjunction with her thrusts, maximizing the depth of her stroke. “I love your cum-hungry ass!” She nearly screamed.

The assgasm, as she called it, gave me a warm, pleasant feeling throughout my entire lower abdomen. It wasn’t a release, like the prostate orgasm from earlier. It was a feeling of intense bliss. Fulfillment. A euphoric state of being where nothing at all mattered except the physical and emotional bliss I was currently experiencing. If Maddie had asked my name at this moment, I likely couldn’t have answered.

She continued for at least another ten minutes, ravaging my quivering hole, keeping me at the pinnacle of my assgasm the entire time. She was saying something, but I couldn’t hear her through the sounds of internal euphoria. I did feel her push my body off her magical, assgasm-inducing appendage and scramble around on the bed. My rag-doll body was shaking uncontrollably as she quickly draped my head, backwards over the edge of the foot of the bed and mounted my mouth. In one quick stroke, her balls were resting on my cheeks. She roughly pounded my throat another dozen stokes or more then filled my stomach with her gift of sticky cum. I don’t even remember her pulling out of my mouth, but I do recall coughing a little as I tried to breath in a thin stream of cum that she left as her massive cock pulled out of my mouth.

I tried to speak, but my stretched and sore throat couldn’t produce any sound above a whisper. Maddie bent down to put her ear closer to my mouth and I was able to whisper, “Thank you for my gift.”

Maddie laughed and hugged my body. The quivering had nearly stopped, but I could still feel the spasms in my anus and the warmth that spread from that center of pleasure through the rest of my body. She broke our encounter and disappeared for a moment—or I passed out—I don’t know which, but she returned with a warm wash cloth and was gently cleaning my face and neck. She then reached down and cleaned my bottom before she scooped up a pool of my pre-cum that had leaked all over my legs and groin. She fed it to me and I happily licked her fingers clean. “Thank you…” I croaked before the darkness took me and I passed out.

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