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100 NSFW Asks (a shy guy's world mlm edition)
I mixed nsfw ask games I found online together and filled the holes with some of my own questions. Everyone who asks off anon can get a free nude (dick or hole). This generousity is a result of me reaching the 1500 followers mark. (Yay! \o/) This offer ends on sunday, 06.09.2020. Letâs begin!
1: When did you lose your virginity?
2: When you lost your virginity, was it intended or spontanious?
3: Do you like rough sex or soft sex?
4: What was the weirdest place youâve had sex?
5: Whatâs your favourite sex position?
6: Do you like to be dominant or submissive?
7: Are you a top, a bottom or verse?
8: Do you prefer sex on the bed, couch or the floor?
9: Have you ever had sex in a public place?
10: Have you ever sent someone a dirty text or picture?
11: What does your favourite sexy underwear look like?
12: How often do you have sex?
13: Is there anybody right now youâd like to have sex with?
14: Do you prefer giving or receiving oral sex?
15: What was the most embarrassing thing thatâs ever happened to you during sex?
16: Name a song youâd listen to during hard, rough or kinky sex.
17: Name a song youâd listen to during soft, slow or passionate sex.
18: Are you into dressing up for sex?
19: Would you prefer sex in the bath or sex in the shower?
20: When was the last time you masturbated?
21: Have you ever been caught masturbating?
22: Have you anonymously sent a sexual ask to someone on tumblr?
23: Do you like using sex toys?
24: How many different men have you had sex with?
25: Is there anything you do after sex? (for example, smoke, eat, drink)
26: What is something that will never fail to get you horny?
27: Do you prefer early morning sex or late night sex?
28: Whatâs your favourite body part on men?
29: What is menâs favourite body part on you?
30: Is there something that you have hidden in your room that you donât want anyone to find?
31: What was the weirdest sexual act someone has performed (or tried to perform) on or with you?
32: Have you ever tasted yourself? If no, would you? If yes, what did you think?
33: Is it ever okay to not use a condom?
34: Is there food that you would like to use during a sexual experience?
35: Whatâs the worst possible time to get horny?
36: Do you like it when your sexual partner moans?
37: How much fapping is too much fapping?
38: What was the best sexual compliment you ever got?
39: What are your favorite foreplay activities?
40: Would you wear lingerie?
41: Is there a fictional character you would have sex with?
42: Do you have any masturbating pictures or videos of yourself?
43: When was the last time you had sex outside?
44: Would you ever have sex in public?
45: Would you ever have a threesome?
46: What is one random object youâve used to masturbate?
47: Do you watch porn?
48: Do you like oral sex?
49: How do you feel about tattoos on someone you are interested in?
50: How would you feel about taking someones virginity?
51: Is there any food you would NOT recommend using during a sexual encounter?
52: Would you rather be a pornstar or a prostitute?
53: Do you have a sexual fantasy you would never act out?
54: Have you ever been called a freak? Why?
55: Do you feel comfortable going âcommandoâ?
56: Would you have a problem with going down on someone if they hadnât shaved their pubic hair?
57: If you could give yourself head, would you?
58: Do you prefer booty or boobs?
59: Have you ever cheated on someone? Why?
60: Have you ever watched someone masturbate?
61: Has anyone ever watched you masturbate?
62: Have you ever seen someone have sex with their permission?
63: Have you ever seen someone have sex without their permission?
64: Have you walked in on someone masturbating or having sex?
65: Have you ever had an erection and someone noticed?
66: What is your method of masturbation?
67: What is your penis size?
68: What is the strangest thing you have ever put up your ass?
69: When was the last time you masturbated?
70: When was the last time you had sex?
71: When was the last time you watched porn?
72: Have you ever bought a sex toy? If so, which one did you buy last? What was your first sex toy? If not, which one do you plan on buying when you do?
73: Are you circumsized?
74: Which not-genital part of your body do you like being touched?
75: Which genital part of your body do you like being touched?
76: Do you like reading erotic stories or comics?
77: When was the last time you have had a wet dream?
78: Have you ever had sex with a woman?
79: Is there a friend you would willingly have sex with?
80: What do you think about group sex?
81: What are your hard limits when it comes to sex?
82: Do you like being called a slut or whore in bed?
83: Are you into any BDSM?
84: Have you ever wanted to have sex with someone but knew you couldnât for any reason? Why?
85: Do you like dirty talk?
86: Are you loud or quiet during sex or masturbation?
87: Have you ever been inturrepted during sex or masturbation? Who or what interrupted you?
88: What kind of porn do you like to watch?
89: Have you ever confessed to someone that you got an erection over them?
90: Have you ever masturbated because your sexual partner wasnât there when you needed them?
91: Have you ever had a one night stand? Do you still keep in contact with them?
92: Have you ever had a friends with benefits? Are they still beneficial?
93: Do you like being called a slut or whore in bed?
94: Do you like dirty talk?
95: Do you like edging?
96: What was the weirdest thing that has ever turned you on?
97: Have you ever posted a nude of you on a website? Did it include sexual actions?
98: Whatâs your favorite porn category?
99: Do you have any kinks or fetishes?
100: Has any of your partners had sex with someone else?
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Stories are fiction and intended for readers 18 and up. All pretend characters are assumed to be legal, consenting adults.
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Shawn awoke on top of Derrick with the morning light penetrating through the hotel window. They were still entwined in an embrace, their scruffy beards pressed together. Shawn softly kissed the nape of Derrickâs neck just as a piercing cacophony of beeps echoed through the room. âFuck,â Derrick moaned, rousing himself from tranquil slumber. âThatâs either your wife or mine texting. Either way, letâs ignore it.â
It was a week before the Sigma Epsilon Chi fraternity alumni weekend when Shawn sent out a request on the alumni list serve: âHotels near campus all booked for the game. Anyone willing to share a room? My wife canât make it, so itâs just me.â Derrick saw the request and immediately offered up his hotel room. âMy wife is pregnant and staying home,â he emailed Shawn. âPlus, it would be great to catch up with you.â
Derrick and Shawn were fraternity brothers. They had been in the same pledge class, but were otherwise in different circles. Derrick was more of a party jock back then, whereas Shawn was a bit more studious and reserved. Although they werenât best buds, they did share one unique bond â they were âbate buds.
Shawn was on his bed and jacking off to porn late one night as a reward to himself for finishing a rather laborious paper for his Poli Sci class. Derrick could hear the soft moaning of pussy porn coming from Shawnâs room and barged in the door. âFuck, man! Donât you knock?â Shawn admonished while quickly covering his hard cock with a pillow. Derrick was trashed and ignored the reprimand. âScoot over, bro,â he ordered while parking his ass next to Shawn on the bed. âI need to bust a nut.â
Derrick then pulled out his huge cock and began to openly jack himself. âMan, Iâve seen this bitch before,â Derrick commented while gesturing to the porn slut on the screen. âIn one of her other films, she fucking took two cocks in her pussy and another up her ass at the same time. Sheâs hardcore, bro.â Shawn didnât react to the bitch on screen and kept staring at Derrickâs big cock. âWhat, bro?â Derrick asked. âYou act like youâve never jacked with a guy before. Come on. Itâs fuckinâ weird if you just watch me. Join me, bro.â
Shawn uncovered himself with the pillow and started to jack his cock simultaneously with Derrick. Watching Derrick jack his cock made Shawnâs dick rock hard. âDamn, bro,â Derrick observed, âYouâre thick as fuck. I bet the bitches love that. Can I feel?â Shawn removed his hand from his cock as Derrick gripped it hard around the base. âFuck,â he exclaimed. âLook how big your head gets when I squeeze like this. Damn.â Derrick began to slowly stroke Shawnâs cock. Shawnâs head rolled back in ecstasy. Girls had never been able to jack him satisfactorily, but Derrick seemed to innately know just how Shawn liked it.
Shawn was enjoying the expert stroking, when Derrick paused and asked, âYou wanna feel mine? Itâs cool, bro.â Shawn crossed his arm over Derrickâs and began to jack Derrickâs big dick. Shawn had never touched another guyâs cock and was mesmerized by the experience. Derrick was cut, like Sean, but there seemed to be more glide to his skin. Derrickâs big, floppy balls rose up and down in unison as Sean worked Derrickâs big dick. He was clearly doing something right, as Derrick soon began to moan, âAww, fuck. Iâm gonna bust, bro. Keep going. FUCK.â Shawn angled Derrickâs cock upward and watched in delight as Derrick sprayed his load all over his bare chest.
âFuck that was hot,â Derrick exclaimed. âNow itâs your turn, bro.â Derrick swiped some of his own cum off his chest and began to jack Shawnâs dick with it. The feeling of being jacked with another dudeâs load was intense, and Shawn was soon blasting his own load. It went airborne and rained down all over his cock and Derrickâs hand. Shawn reached for some Kleenex on his bed table and they each cleaned off their cocks. Derrick stumbled out the door without a word.
Shawn didnât see Derrick at breakfast the next morning, nor at any point during the day. He was nervous about how they might react around one another. Derrick was so drunk, Shawn wondered if heâd even remember what happened between them. Shawn feared that their âbate session would just be a one-off, but soon realized he had no reason to worry. Just before midnight that night, a knock sounded at his door. It was Derrick. He craned his head in the doorway and said, âHey, bro? Feel like jacking again tonight?â
And so began a mutually satisfactory relationship that lasted until graduation. The porn may have changed up from night to night, but their shared objective did not. Each night they jacked each other off â and nothing more. Shawn often thought of sucking Derrickâs cock or, even better yet, bending over for it. But Shawn was too chicken to make a move, and too afraid of fucking up a good thing with Derrick. Shawn regretted not doing more with Derrick back then, and that regret was eating him up when he laid eyes on Derrick at the first night of alumni weekend.
They agreed to meet at the fraternity house before checking into the hotel. There was a BBQ on the front lawn with plenty of beer as alumni mixed with current brothers. Shawn spotted Derrick across the yard. Fuck, he looks hot, thought Shawn. A memory of Derrick straddling him and blowing his load all over Shawnâs chest flashed before Shawnâs eyes. Shawn tried to play it cool, but there was no need. Derrick saw Shawn and made a beeline toward him. âThanks for putting me up in your hotel room,â Shawn said while extending his hand to Derrick. âMy pleasure,â Derrick returned with a wink.
The alumni BBQ itself was kind of a bust. Shawn couldnât remember why he hung out with any of his old brothers in the first place. At some point during the afternoon Derrick sidled up next to Shawn. âMan, being here at the old house sure brings back memories,â Derrick observed while gesturing to the ivy-covered facade of the fraternity house. Shawn gave a polite nod as Derrick continued while leaning into Shawnâs ear, âBut my favorite memory is jacking off with you every night.â Shawn could feel his cock hardening. âYou remember that?â Shawn asked in near disbelief. âRemember it?â Derrick countered. âI often think about it when Iâm fucking my wife. Gets me there every time.â
Shawn looked down and noticed Derrickâs pants were also tenting. The BBQ wasnât even half over, but Shawn didnât feel like waiting. âHey, man?â Shawn asked while placing his hand on Derrickâs back, âHow about we skip the rest of this BBQ and head to the hotel?â
Derrick had reserved a small suite, which included a king bed and a sitting area with a couch and television. Shawn immediately suggested they download some pay-per-view porn and jack each other on the couch. âFuck that,â Derrick objected. âWeâre not two naive frat boys anymore. I want you on the bed.â Derrick nearly tore Shawnâs clothes off while shedding his own attire. They were soon naked on the bed with Derrick on top of Shawn.
âFor so long,â Derrick began, âIâve regretted that we didnât do more than jack off back then. I vowed that if we ever had the opportunity to be together again, I wouldnât waste the chance to be inside you.â Derrickâs lips were hovering above Shawn, their breath commingling. Shawn raised his head to meet Derrickâs lips and kissed him deeply. âI want you inside me,â Shawn moaned as he reached down between them and felt for Derrickâs hard cock.
Derrick quickly pushed himself up, pinned Shawnâs legs over his head, and began to probe Shawnâs hole with his tongue. âFuck, man,â Shawn moaned. âThat feels so fucking good.â Derrick gave a chuckle, saying, âJust wait until youâve felt my cock.â Shawn didnât have to wait long. After getting Shawnâs hole wet and open, Derrick began working his big cock inside it.
âFuck,â Derrick exhaled upon getting his cock balls deep inside Shawn. âYour hole feels so fucking good.â Shawn instinctively raised his virgin hole slightly, attempting to take Derrick even deeper. Derrick was giving Shawn some slow, steady thrusts when he reached for Shawnâs cock and began to jack it with a similar rhythm. âDo you remember when we used to cum at the same time?â Derrick asked. âI donât know how you were always able to time shooting your wad at the same time as me.â Shawn gave a little laugh, âIt was easy. All I had to do was look in your eyes and see the intensity on your face when you were about to bust. Seeing that look,â Shawn confessed, âalways turned me on and made me shoot along with you.â
âLetâs see if youâve still got it,â Derrick challenged as he began to jackhammer Shawnâs hole while jacking Shawnâs cock with matched intensity. âAww, FUCK,â Derrick was soon roaring. âIâm feeling close. You ready to shoot?â he asked Shawn urgently. And while looking deep into Shawnâs eyes, Derrick let out a bellowing, âFUCK YEAH. Holy fucking SHIT,â as his balls emptied inside Shawn. Almost on cue, Shawnâs cock erupted and sprayed his thick load all over Derrickâs hairy chest as he hovered above Shawn. Derrick collapsed upon Shawn, mashing Shawnâs warm, sticky load between them.
âDamn, Iâve made a mess of us,â Shawn laughed as Derrick rolled off of him and onto the bed. âHow about we hit the shower and maybe order up some room service. Iâm starving.â It would be awhile until they ate, as Derrickâs cock found its way back inside Shawn in the shower. An hour later, they finally ordered up some food. They ate hurriedly and then fucked again on the bed. Shawn rode Derrickâs big cock cowboy style and then collapsed upon him, their bodies entwined as they fell into blissful sleep.
Shawn was still asleep on top of Derrick when the beeping of a text startled them late the next morning. âItâs one of our wives,â Derrick warned. âJust ignore them.â Shawn sat up and took a quick glance at his phone. âNo,â he corrected. âItâs actually one of the alumni weekend organizers. He texted that the tailgate party has already started and wants to know if weâre still coming to the game.â Derrick yawned and scratched his scruffy face. âFuck âem,â Derrick barked while pulling Shawn back into his arms. âYou are why I came here this weekend. Now letâs break this fuckinâ bed.â
Stories are fiction and intended for readers 18 and up. All characters are assumed to be legal, consenting adults.
I was a frat boy back in college I wish I had a relationship like that with one of my bros