Humiliating Nightmare
Bdsm Story

Humiliating Nightmare

by Lynussmall 19 min read 4.1 (7,100 views)
sph humiliation cucold
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Sorry about the typos. I have to drink to get this out. The story continues. This is painfully true. All participants were over 18.

Lisa and Jay were out partying, but Lisa was living with me! I'd failed to please her a few times but seemed eager to help me with my penis problem -- "prejack" as she calls it. Most importantly, she liked me. She'd moved in, and told me we'd work together to get me to last. Before she left for the weekend with her best friend Jay (who had incriminating pictures and videos of me) she'd instructed me on things to do, such as unpack her clothes and put everything away. She'd also told me not to jack off, as she was going to work with me to make me last. She didn't seem to mind that I was small.

Her friend Jay was another story. She just seemed sadistic. I couldn't believe I had all this drama with hot girls; they were both way out of my league. The morning that Lisa took off was very busy for me. I worked all day. I incorporated her stuff into mine, unpacked all her clothes, and stored a lot of my clothes in a big trunk to make room for all her sex clothes. I put away her panties, her dildos, everything! It was great. All her stuff was so girly, so f*&king sexy.

It was great until 2:00 A.M. that evening. I got a text from Jay. She'd text me before with an address and a time to arrive, in 8 days, and she'd said she'd share the pictures and videos with all our friends if I didn't show up when instructed. 9 PM on the 28th at an address a few blocks away. I knew about that complex because it was famous for partying at our University.

The cops were there all the time, and there'd been a few riots at group parties where the whole complex would throw a wild multi-party. What in the flying f&$k was going to happen on the 28th.

Her 2:00 AM text read, "So I heard Lisa has moved in with you. Is she your girl friend now?!"

Me: "I really like her. She moved in yesterday."

Jay: "So is she your girlfriend? Tell me the truth. I've a group text for most of the people that were at that party. Answer or I'll send that group the VIDEO of you jerking off with your best friend's gym pants around your extremely LITTLE d!cklet. IS LISA YOUR GIRLFRIEND OR NOT? Answer me now!"

Me: "Yes. I think she is my girlfriend."

A few mintues past. Why was Jay asking that? It was weird. Of course I didn't trust her. She was blackmailing me.

2:30 AM

Jay: "Lisa said you're putting all her clothes away in your apartment. Have you finished? Is your apartment clean?"

Me: "Yes. All her clothes are put away and I've cleaned the apartment, and decorated it with her stuff like she asked me to do."

Jay: "Lisa is so drunk. We're coming over. Want to see your girlfriend?"

I was both excited and nervous. Mostly nervous. Lisa was a nice, but when she drank, she was a little less nice, and when she was with Jay, there was a side of her that scared me a bit. Not as much as Jay, but still.

Jay: "Answer me please. Do you want to see your girlfriend?"

Me: "Yes, please come over. I'd love to see Lisa. Your always welcome." Maybe I could make friends, be really nice, and get on Jay's good side. It appeared Lisa was my girlfriend, so maybe I had an in with Jay.

Jay: "Here she is!" A moment later Jay text me a video. It was Lisa dancing with Paul no less. Paul had been in the room when Lisa had made me come with 1/2 pump in front of Jay and not one but two freaking Lisas -- the Lisa that was living with me and, the other Lisa, my best friend and crush from highschool. All of them had seen me come immediately when Lisa touched my little d!ck at the party, and I was pretty sure Jay had videoed it, amongst other humiliating adventures that occurred the next morning (also in front of Paul after he had f*&ked Jay all night with a tree truck d&ck).

Anyway -- the video had Lisa dancing, or more accurately gyrating, against Paul. Paul had screwed Jay in front of Lisa and me, and had brought Jay to at least three organisms. His d!ck was long, but even more, it was very thick. It made me look really small in comparison. I couldn't believe the video, Lisa was acting so sexy. You could tell she was drunk and had very little inhibitions. Her top was sliding down on both shoulders, and Paul's hands were on her hips as she gyrated against him.

Jay: "So what do you think? BTW -- Lisa told me you're not her boyfriend but that she is helping you with something. What is she helping you with? Don't lie. I will know, or I can find out. Lisa spills it all when she drinks."

I searched my brain for a lie, then realized if she didn't believe me, she'd ask Lisa. When Lisa is drunk, she is loose lipped as hell.

Jay: "Answer me Lynus! I'm not appreciating this attitude. I think I'm going to text a pic of you coming on those running shorts. I better like your answer, and it better be true."

F*&K I didn't want to say it.

Me: "Lisa is helping me with my premature ejactulation problem."

Jay: "I knew that. He he. She said you're a "pre jack! She actually googled that sh!t. Ha ha."

About twenty minutes passed. There it was in writing. 1 -- Lisa said she wasn't my girlfriend, 2 -- Had told my secret, and 3 -- I'd admitted in writing that I was premature ejactulator. How did I get here?!

3:00 AM

Jay: "We're coming over. Lisa is hammered. Dress in those little green shorts. Wear nothing else. Don't argue. Don't beg. We'll be over in about 15 minutes. Lisa doesn't have a key. You'll answer the door in those little green shorts. You won't tell them I made you do it. You'll tell them that it makes you feel sexy. You will be convincing or the group text will go out with your little perv show."

3:10 AM

Jay: "We're in the cab. Better get ready. We're bringing Paul! See you soon STUD! Ha ha! I have got you by the little balls Lynus! Ha ha!"

I was in a cold sweat. She had me. But what was worse, that video going out to everybody, or wearing those shorts and suffering a little embarrassment in front of Lisa, Jay and Paul! Again!

The video could NOT GO OUT. It was the worst. I decided better to be embarrassed in front of Lisa, Jay and Paul, then for the video to go out. Especially since on that group text was my best-friend/crush, "the other Lisa."

I know it's confusing with the two Lisas. But there really were two, and yes it was confusing. Both hot blondes. Both lived in the same apartment for aobut a year. And both had seen me prejack -- as Lisa calls it - on myself after a 1/2 pump. The confusion between Lisas resulted in another humiliating experience that ended my friendship with "Highschool Crush Lisa." But that is a story for another day. I'm sensitive on that subject, I still miss her terribly, and can't get myself to write it out right now. My therapist says I need to work on that and put in on paper for our sessions. I'm just not there yet.

Anyway, I depressingly digress, I decided I really didn't have a choice. I stripped down and put on the little green women's running shorts. They were so tight on me and outlined my little d!ck. I rubbed it and got semi hard, trying to look better in the shorts. It looked a little better with a half chubby, but not that good. I looked more like a girl; an ugly girl.

3:15 AM

Jay: "Picked up some wine. Remember, tell them you're wearing it because "it makes you feel sexy." And be convincing. DON'T tell them I made you do it. Or else. Tell me you understand pin d!ck."

Me: "I understand. I'm wearing the shorts."

Jay: "I'll bet you rubbed your little d!ck trying to make it look bigger in the shorts. Am I right? Don't lie."

How the hell did she know? I found myself answering honestly. "Yes. I rubbed it to make it look bigger in these shorts. They are very tight on me."

Jay had a power over me know. It was almost like I couldn't control my own actions. I just did what she said, and didn't dare lie to her. Somehow I knew she would know. How the hell did she know I was rubbing my d!ck to make it look bigger in those shorts? Damnit! I was lost in thought, and a surreal real-time panic that is hard to put into words. I felt so damn naked in those green shorts -- more naked than just naked.

A knock on the door shook me out of my panicked fog. I could barely move. I stood frozen in front of a mirror in the hall looking at the tiny bulge. A second knock was louder and I could hear giggling on the other side of the door.

I opened the door. I wanted to cover up my shame but I somehow knew that would antagonize Jay. She wanted to utterly humiliate me. And I knew I had to say the green shorts made me feel sexy. I was shaking.

Lisa was standing at the door.

Lisa: "Wow! Somebodies partying. We have wine! Why the hell are you wearing those Lynus? Wait, look out, I have to pee. You are so crazy. You look ridiculous."

Lisa brushed past me and walked briskly to the bathroom, giggling all the way.

Paul: "What do we have here? Dude! What are you doing? Why those... oh my god... those are the shorts you had that morning when you... I need a drink. Dude, what the f*&K?"

Paul brushed past me. I didn't answer his questions. I hoped to skirt the issue.

Jay stood in the door way with a huge grin on her face.

Jay: "Hey sexy! Why don't you answer Paul's question. He asked you what you are doing?"

Lisa responded from behind be. You're little but looks so funny in those shorts. They actually kind of fit you. Turn around. Let me see you from the front.

I slowly turned around. I wanted to cover up the front. My d!ck looked tiny. I couldn't look down at it; I knew it was a little outline of an even littler nub. God I'm pathetic. I couldn't get hard. This was not sexy. This was terrifying. I turned around to a click of Lisa's phone.

Lisa: "Ha ha. You are crazy Lynus. What's with those shorts?"

I knew how I had to answer.

Me: "They make me feel sexy." Jay, now standing behind Lisa, gave me a serious glare. Like she was threatening me. I knew what she wanted. She wanted me to sell it.

Me: "I like to wear them because I feel very sex."

Lisa was swaying back and forth, looking like she was going to fall. She was hammered.

Lisa: "Oh my god Lynus. You were jerkin' your little girkin weren't you? I told you not to jack off, "PreJack", so we could work on your problem. This is not helping. Were you jacking off?"

Paul: "Dude, WTF... this is too much Dude, too much."

Again, Jay was glaring at me. It was so threatening. I knew what she wanted. I answered Lisa and was mortified by the waves of humiliation I felt as things seemed to be getting worse and worse.

Me: "I'm sorry. Yes I was jacking off. I feel sexy." I was hoping I was selling this.

Lisa: "Paul. Can you help him? I can't seem too. He couldn't get hard this morning, then when he got a little hard he came immediately!"

Paul: "This is between you two. I'll stay out of it. Didn't your promise me a lap dance by the way? I did when the game. You did promise sexy."

I couldn't believe it. Jay was going to give him a lap dance. I felt a stir in my d!ck.

Lisa: "Fine... fine. Let me get some wine."

WTF -- Lisa was going to give him a lap dance. WTF!

Lisa was so drunk and spilt wine as she poured a full glass of red. "Lynus I need you. Can you clean this up? I made a bet and lost and know I have to give perv here a lap dance. You don't mind do you Lynus? Maybe you could learn something from your friend."

"Friend I thought, yeah right." I guess I couldn't blame Paul, but I did feel serious resentment, mixed with envy, regret and humiliating.

Me: "Not at all. I'll get a towel," I answered Lisa as I began cleaning up the wine.

Lisa: "No. I mean you don't mine me giving your friend Paul a lap dance. This is your apartment.

But it's Friday. Let's party. Woohoo." She was so hammered.

Jay: "Well Lynus. You don't mind do you? You feel sexy in your little shorts don't you. You want to watch Lisa give Paul a lap dance don't you?"

Me: "Yes, please. I don't mind."

I cleaned up the wine as Lisa put on a one of my old records. She was swaying too and fro and was looking sexy as hell, although obviously hammered. Lisa started dancing sexy in front of Paul who was sitting in on the couch. Lisa looked so hot and Paul had a huge grin on this face as he watched Lisa gyrate in front of him. He looked so confident. My envy was raging.

Jay: "Lynus... they can't have all the fun. Take off your shorts and show me your little d!ck. I want to take of picture of you while you watch Lisa. You look so silly. Take them off."

Paul: "Don't do it Dude. You'll regret it!"

Lisa was now sitting on Paul's lap. Jay was swaying to the music. "Take them off Lynus," Jay commanded as she glared at me. Lisa was rubbing her hot little short dressed ass on Paul. Her skirt was pushed up her hot, long and muscular legs. I felt a stir in my d!cklet. Lisa and Paul were no longer paying Jay and I attention. They were staring into each other's eyes with lust.

I turned around to take off the shorts (to give my self just a small bit of privacy). I knew I didn't have a choice. Jay whipped off her top and threw it at me. "Turn around and show me that little d!ck." I turned around to see Jay pointing her phone at me, wearing a sexy bra and tight skirt. I didn't want to give her more ammunition to blackmail me, but what choice did I have. "Look into the camera and take off your girly little shorts."

I glanced over at Lisa, hoping maybe she would defend me. What I saw made my stomach drop. Lisa and Paul seemed oblivious to my situation, and Lisa was biting Paul's lower lip. Paul had his hands up Lisa dress, she was sitting on his lap and facing him. Paul was clearly rubbing her ass.

Jay: "Lynus!"

I slowly slid the shorts down. Jay's camera light was in my eyes and very bright. I squinted past the light to see Jay's huge grin. She stumbled back on her high heels and kicked them off in a drunken dance like motion.

Jay: "Give our viewers a show Lynus! Rub your little d!ck." Viewers?

Lisa looked up from Paul's lap. "What the hell are you two doing? Lynus, are you getting frisky with Jay. You know that you're just going to blow your load prematurely don't you Prejack. Can you even get hard this time." Lisa seemed to like the name "Prejack."

Me: "Yes, I mean know..." I was lost in thought. I felt dizzy with humiliation and fear. I felt ill.

Jay: "Rub your little d!ck Lynus." I glanced back at Lisa and Paul. Paul was amazingly taking down Lisa's panties while she was sitting on his lap. He looked so happy. He looked so confident. And Lisa looked liked she was lost in lust.

Lisa was staring into Paul's eyes. "I've wanted this Paul. I'm sorry, but you have a beautiful d!ck."

Jay snapped me out of my leering. "Rub that little d!ck Lynus Small." Jay was dancing in her bra and a sexy mini skirt.

Lisa: "It's ok Lynus. It's a party. You can get with Jay. Just try not to prejack." Lisa turned back to Paul, "fuck me Paul. Jay can't stop talking about you. You are so damn hot."

I was rubbing my flaccid d!ck. Although I couldn't get hard, the girls looked so sexy. Both of them looked slutty, but good-slutty. My d!ck remained soft as I pulled my little d!ck, and massaged the head trying to get hard.

Paul: "Hell yes girl, but not here. I'm not into the Orgy thing. Let's go to my bed. I've got some weed at home too. I will give you want you want. Let's go sexy."

Lisa, looking a little disappointed, "Ok, but we sure as hell can't drive."

Jay: "Naked Lynus will drive you. I'm going to crash here. But Lynus will drive you guys, he hasn't been drinking, and would love to drive you two over there butt ass naked. Right Lynus. You want to drive them over to Paul's house so he can ravish Lisa? Don't you? You don't mind Lisa getting slutty with Paul, do you?"

I'd never felt so naked.

Lisa: "You two are so crazy. You're a good match. It's ok, right Lynus. We're just having some fun. Try not to prejack. Jay hates that."

Me: "ahh...."

Jay: "Get your little gerkin hard."

Paul: "Hurry up you two. I need to take this girl home. Why are you video taping him? You two are nuts."

I was still trying to get hard. Jay sauntered over to Lisa. "Here take this. Video this one. It's hilarious." Jay handed the phone to Lisa. The light was still on -- it was clearly still recording my shame.

Jay walked back over and stood in front of me. My thumb and index finger were frantically rubbing trying to get hard.

Jay: "This is pathetic Lynus. This is just sad. Let me try. But don't come until I say."

While Lisa pointed the phone at us, Jay reached out and slapped my hand away.

Jay: "Let me see that little d!ck Lynus." Paul and Lisa were giggling as Lisa slipped her panties back on. God that was sexy. Paul was now holding the phone, pointing it at us, but he was looking away. He clearly did not want to see this and seemed impatient to leave.

Jay, with my d!ck in her hand, whispered in my ear "I'm going to ruin you."

Jay got behind me, and turned me so I was directly facing the camera, which was now again in Lisa's hands.

Lisa: "Let's hurrying up. Paul and I need to leave." She giggled, "I am so horny she whispered to Paul" I noticed Lisa's other hand was on Paul's pocket, which outlined a thinkness.

Jay, standing behind me, reached around and grabbed my d!ck. I felt her other hand reached between my legs with her other hand. She patted my ball sack, leaned in, and whispered again, "I'm going to ruin you."

Jay started rubbing my d!ck in an incredible way. She really, I mean really, knew what she was doing. It was incredible the way she worked it.

Lisa: "Jay -- do that thing that your weirdo ex always liked. I dare you. I'll bet Lynus blows in under a minute if you do."

Jay, still jacking off my now semi hard d!ck, said "gross, no way you slut."

Lisa: "Come on! I dare you b*&tch." Lisa giggled uncontrollably.

I was now fully hard now. The banter between Lisa and Jay was turning me on.

Jay: "You had to dare me. You owe me for this one. You get Paul tonight and I get this little thing!"

Lisa: "I dare you."

Jay: "Fine. You are crazy girl!"

Jay reached her other hand around my head, and said "open up."

I opened my mouth to ask her what she meant, but before I could speak she slipped her middle finger into my mouth. At the same time she gave my balls and d!ck a little squeeze.

The next thing I felt surprised the hell out of me. With my package in one hand, Jay slipped a finger into my azzhole. It hurt and I clinched my butt cheeks. "Don't clench pin d!ck. Push out like your trying to fart, it will go a lot easier."

With that I felt a painful pressure as I felt more finger, or fingers, enter my azz. "Push against it pin dick, it will go easier."

Lisa: "Yeah Jay! Fuck that little pin d!ck. Ha ha! Just kidding Lynus. It's a party!"

Despite the pain, I was hard as a rock. Lisa being mean was turning me on. Jay was still holding my d!ck and balls. She wasn't rubbing me but she was fingering my asshole.

Jay: "Tell us how much you like it."

Me: "I really like it." I lied. This was humiliating and painful. I was aroused, but the fingers in my butt was too much. Jay gave me balls and d!ck another squeeze.

Jay: "No. Tell the camera." I'd almost forgot, and turned back to Lisa filming with Jay's phone and giggling. Not a nice giggle, a little sadistic sound to it.

Me: "I like it."

Lisa: "You like what Lynus. Tell us."

Me: "I like that Jay is holding my penis. She is very sexy."

Jay: "No. Tell them what you really like." I knew what she was talking about.

Me: "I like you fingering my butt."

Jay: "Then you'll really like this." With that I felt a sharp pierce at my ass, and then the sound and feel of vibration. I realized Jay had somehow grabbed Lisa's pink dildo. She must have gotten it when she went to the bathroom. She was planning this! My ass felt a pain I'd never felt before. "Take it b!tch. Now rubbed your little d!ck Prejack!" That nickname was catching on.

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