sleepy's day 2/2 (smut)

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Nightmare pov:

We all got ready and headed to outertale. The second we walked through the portal sleepy looked around mesmerised alone with the tentacles. I chuckled. They had been to outertale a few times with me and everytime stared at the stars. "Heh can't take your eyes of em huh?" I said bumping sleepy's elbow. He shook himself out of his daze and looked at me and smiled. We all began walking around looking at the stars and enjoying ourselves. We kept asking sleepy questions about his life as a tentacle "ok I got another one. Do you look at the other tentacles as like boyfriend's oooor?" Killer said "eeewwww! No way. We call each other brothers since we are stuck together and all appeared at the same time in the same place" he said "in that sense... Wouldn't nightmare be more of a dad?" Horror asked. I thought for a second "hmm nah" sleepy said.

We all continued untill we reached the end of the floating rock and stared out at the endless space. "Uhh why don't we go get some nice cream and leave these two be?" Error suggested. Everyone agreed and left leaving me and sleepy alone. We sat at the edge of the cliff and began having a nice chat about things that have happened to us personally in the past. "Hey I wanted to ask something kinda personal..." I said rubbing my neck with a blush "shoot" sleepy said "... What's it like going umm... Inside me?" I said. I was genuinely curious about it and knew he would have no problem answering. He smirked at me "throat or pussy?" He asked. I hesitantly said pussy "well at first it's like a big warm wet blanket and when you start thrusting it tightens around you. I don't think you realise it but you are extremely good at clenching and crush us slightly, especially when you cum. It's really hot~" he said grinning. I blushed madly "when you cum it feels like being squirted with warm mayo kinda. We normally end up absorbing your cum because it tastes really good~" he said. I felt myself get aroused and was worried the others would try something but they seemed to leave me alone "alright now you tell me what's it's like having us in you?" He asked. I paused for a minute trying to think of an answer "well... It's a lot different to a penis, it's way better. It's more directed and a lot more aimed. When you have sex normally it's kinda willy nilly since you don't know where your going or what your really doing but you guys get a front row seat to what your doing and can go exactly where you know I want you to go. There is no teasing or anything in it... Well unless you purposely tease me" I said. I looked and saw sleepy almost drooling "I really hope I get to be a tentacle again" he said. I chuckled before taking his hand and holding it. We both stared at the stars for a few minutes taking in the piece full moment "the stars are beautiful" sleepy said "yeah..." I said. He leaned on my shoulder and I wrapped an arm round him "not as beautiful as you tho" I was thrown of by the compliment but enjoyed it anyway. After a little longer everyone came back and gave us both a nice cream. Sleepy ended up getting brain freeze from it since he is a dumbass though.

We whent home after a few hours and started watching movies but I was to distracted looking at nice places to take sleepy out on my phone. I place that seemed alright that I could book for tonight. I booked it and continued to watched the movie. Sleepy leaned on my arm and I got an idea. I picked him up and sat him on my lap wrapping his legs around my waist. He seemed surprised but I just layed his head in my shoulder "you can rest if you want" I said rubbing his back. He let out a small human before relaxing and falling asleep very quickly. I continued to watched the movie with everyone for a while untill time came for the date. I woke sleepy up and let him know. We both got up and I grabbed a few things before we left. We arrived at a restaurant I had booked and sleepy looked impressed "woow I've never been to one of these before" he said. I chuckled and took his hand walking inside. We whent to our seat and began chatting. I taught him a bit about how to order food and what the food were and we managed to order our door without drama. I could tell sleepy was a bit anxious about all the people and took his hand "hey... It's ok. I got you" I said. He looked at me with with a warm smile and I felt my heart melt into it. He continued the date having fun and then I asked if he wanted to try alcohol, he hesitated but agreed and by the end of the night we were both a bit drunk. We headed home and when we walked in my room I pinned him to the door "huh- nightmare?" He asked confused. I lifted his chin and kissed him. We started a passionate kiss with each other. Eventually I licked his lip and he caught on opening his mouth. I shoved my tongue in his mouth feeling his long tongue wrap around mine. His tongue reminded me a lot of the tentacles but not as goopy. I moved my hand down to his waist line and slowly slid then under his shirt. He seemed to get a little worried and pulled off "did I do something wrong?" I asked worried "I'm top" he said sternly. I chuckled bending down slightly and bit into his neck "your not in a situation to bargain~" I said. He let out a small whimper "f-fuck you" he said. I thought for a second "tell ya what. Since you have no clue what your doing I'll ride you once then after you let me fuck you?" I said. He thought for a second "yeah that sounds fair" he said "great" I said picking him up. I threw him in the bed and crawled onto his lap. I could see a huge blush on his face as he smirked "fuck that's hot~" he said. I smirked lifting his shirt off. I took mine off starting to summon my female body. He started to summon a dick "huh. Looked like he have similar ecto magic" I said a little surprised "what you think I was just gonna pop a dick out from under my skin?" He said bluntly "I mean some monsters do it that way" I said Shrugging. He gave me an annoyed look. I pulled his pants and boxers down letting his cock spring out and I was shocked when I saw it, he seemed a little surprised too. It wasn't a normal dick it was just a tentacle looking thing? I blushed seeing it "like what you see~" he said teasingly. I smirked at him before getting off and taking my clothes off. As soon as I was completely naked and had my body summoned I crawled onto his lap again and without any warning slammed the entire thing inside me. "Aahhh~! f-fuck~" I moaned throwing my head back. He was surprised let out a moan to "f-fuck~ is this w-what it feels like~?" He asked curiously. I smirked nodding. He gripped my hips and I slowly started bouncing. He let out a surprised moan not knowing what to do. I layed him back on the bed so he was laying on his back and began rolling my hips and bouncing as much as possible. He didn't really know what to do but seemed like he was enjoying it "ngh~ t-try thrusting your hips up~" I said wanting more of him. He grabbed my hips and thrusted up into me. I let out a loud moan and continued to bounce. I felt his tentacle dick begin to wiggle around in me and let out a cry of pleasure. "Hold on- I wanna try something" he said. He concentrated for a second and I suddenly felt his cock begin to vibrate. I moaned loudly tightening around him as much as possible. We continued for a while untill sleepy for a little finicky "you alright?" I asked "can we change the position?" He asked. I thought for a second before rolling as over so he was top. He sat up and wrapped my legs around his waist. Bent over and bit my neck beginning to thrust. He kept getting faster and faster and I kept moaning louder and louder untill the room was drowned out with the sounds of blissful screams and creaking of the bed. He started pounding me like a wild animal. I whent limp letting him take whatever he wanted from my needy hole. I came pretty quickly but he didn't seem to notice to much, he was to busy trying to cum himself. After a little longer he did cum but kept going even harder. I wasn't ready for it and was a little surprised but liked where this was going. He made me cum multiple times very hard and every time I felt a little more bliss. He came in me a few times as well, I was glad I had taken a pill because I had no clue if he would get me pregnant or not. After a few hours he had finally had enough and pulled out. You could see a small white blob in my stomach you could see through my ecto body where he had filled my completely full of his cum. I looked down and took pride in it slightly. He fell back panting like a mad man. We both layed there for a few minutes getting our senses back "that was awesome" sleepy said. I chuckled "yeah it was" I replied. We both sat there for a little longer untill I sat up "you gonna let me fuck you now?" I asked he sat up and looked at me slightly surprised "forgot about that-" he said. I laughed before jumping on him and summoning me male body. He was a bit surprised but I didn't care "summon a female body" I said. He paused for a minute and then his dick disintegrated revealing a pussy for me to pleasure~. I began kissing him. I slowly lined my dick up and with one thrust whent all the way in. He let out a cry of pleasure and I used it to shove my tongue back in his mouth. I began thrusting and let me tell you, I've never felt a more pleasurable cunt then his~ he was extremely wet and slimy inside and it felt like it whent in forever. He was extremely tight without clenching and when he dick clench I struggled to pull out slightly. I became addicted to his needy hole and began fucking him as hard as possible. I wanted to fined his g-spot but he was so deep I knew I would have trouble.  I tried changing my position slightly to get inside him more. I lifted his legs over my shoulders and began pounding with full force at his tight hole. He layed there moaning and screaming for more trying his best to keep up. I kept going feeling him become insanely wet. The way he was clenching around me I felt myself become close very quickly. I kept going for a little longer before cumming in him. I panted for a second before continuing. Because he was clenching so tight my cum didn't leave his cunt instead stayed inside it along with me and helped as a lube. I continued to pound into his small figure untill I felt him cum aggressively onto my cock. He let out a loud shout and began twitching. I gave him a minute to calm down and continued to fuck him. I kept trying to push deeper and deeper to fined that one little pleasure button, after a couple more attempts I hit something and felt him clench insanely tight, I'd don't know it was possible to go that tight. He let out an even louder scream and I felt him cum again. I grinned knowing I had found it and began trying to aim for it. I pounded into it making him cum every couple thrust. I loved seeing the look on his face as he lost grip of reality and drowned in his own orgasms. I decided to let myself cum one more time before pulling out. I whent as hard as I could untill I felt a second knot build up quickly and squirted into him again. I stopped and took a second to catch my breath. He had gone limp and stopped clenching me. I slowly pulled out and heard a slight pop as I did. My two loads leaked out of him into the bed and I was slightly annoyed since I knew I had to clean it up. I picked him up and layed him in a different spot of the bed and layed next to him letting him cuddle up to me. He passed out almost immediately and I chuckled slowly falling asleep.

A/N

Hope you enjoyed!

(16 July)

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