The un-Tentacular Date

The un-Tentacular Date

HOME/Dear Prudy: Advice on manners and morals.

Willow Rouge
Photo by Teresa Crustacean

In a live chat, Prudy advises a woman whose cute date just can’t stay focused.


By Willow Rouge|Posted Tuesday, June 6, 2013, at 2:30 PM

Willow Rouge, aka Dear Prudy, is on weekly to chat live with readers. An edited transcript of the chat is below. Dear Prudy delivers erotic advice and stories throughout the year. To send questions to Dear Prudy, visit the Eroticwriter Contact Page.

Q. Tentacularly Confused: I went on a date with a man who lives in my building. He’s always been quiet and keeps to himself, but he’s also always been nice and helpful to his neighbors. Last week he asked me out on a date. As I’ve always thought he was kind of cute, if a little eccentric, I accepted. He was wonderful. He was funny. He was polite. He was considerate. But then when we were sitting at a booth having dinner, I noticed an Asian girl sit at the next booth, right behind him. She was peitite and wore a short skirt and tight top, the kind of girls guys always notice. I didn’t think anything of it until I heard the clatter of her silverware on the plate. I could see behind him that something had surprised her. She pressed her back against the bench. She looked down.

We were around the corner. It was late, so it was just us and the woman. We were around the corner from the front door. She looked that way, like she was going to call for the waitress, then she gasped. Her hands grabbed the edge of the table, and her head flipped back. She let out this choked little groan. I couldn’t see it all, because my date was opposite me and in front of her. Her back was to both of us. I knew what was going on but he talked to me like nothing was happening.

the un-tentacular dateBut we both knew. The girl has reached between her legs like she was trying to hold something, maybe to keep it from going deeper, or to pull it out. Her shoulders were hunched and then shes’d fling her back. mouth open, eyes half-closed. All of a sudden she let go and grabbed the edge of the table again. This time she stooped over, until her head almost touched the table, and I just knew was adjusting, opening her legs, helpless as the thing just kept sliding in and in, stretching her more nad more. My date had quit talking. He was just smiling at me, watching me. I didn’t know whether to be hurt, or jealous, or turned on. I kept looking over his shoulder. Dear Prudy, I know it was wrong. No, this was terrible, a terrible thing to happen to a poor unsuspecting woman. But I couldn’t stop. My own legs were open and I was touching myself.

That’s when the girt turned around, just her head. She looked right at me. Her little face was a mask of agony, that kind when a girl is totally full, and stretched, and short of shocked. It’s that feeling when you just know you’re going to give in. You just know there’s no escape. He’s deep inside you’re going to come with his semen. She saw me. She knew I was masturbating. She turned. She awkwardly slid out of the booth and feel to her knees, her hand on her belly. That’s when I could see it all. Her back was arched and her ass was sticking out, you know? The way girls do when we’re being fucked from behind? – when we’re, like, hooked on a boy’s cock. She pressed knees together., but most of the tentacle was inside. The thick part was stretching the lips of her pussy into a big O, like you wouldn’t the un-tentacular datebelief a pussy could be stretched. She had been wearing these tight black panties and crotch was pushed to one side. She pressed on her belly and pushed back with her ass, like she was trying to push it out, but just a little trickle of moisture dripped down the tentacle.

The tentacle had these beautiful, greenish, iridescence scales. I could tell he was proud of them. He was kind of showing off.

The Asian woman tried to crawl forward a little, but his tentacle stayed inside her. She crawled maybe a yard on her hands and knees. Just seeing her back arched like that while she crawled, seeing her hips lift left, then right, then left, all while this huge tentacle was penetrating her from behind, almost made me come. The lips of her pussy were completely stretched and her clit stuck out like a little cock. I wanted to touch it so much.

The girl had sort of given up. Her chin was on the floor. She had widened her knees and her mouth was open. She was gazing toward the front of the diner, her forehead creased. Both hands were palm down. One was at her side, elbow up, the other was stretched ahead of her, like she pull herself just with the tips of her fingers. The tentacle pushed just a little inside her, rippling like a snake, and she froze. She lifted her pussy, her belly bowed downward, and she widened her knees like she was bracing herself or submitting.

Another of his tentacle slithered over her spine, twirled in her hair, then yanked her head back.

the un-tentacular date

I couldn’t help myself. I went over to her. She was in a daze. I put one finger in her mouth and she began sucking. I had to touch her clit, her little cock, stretched, sticking out, and jutting downward because of the tentacle stretching her. I touched it, ever so lightly, with the tip of my finger. Her eyes rolled and she spurted, a hard spurt that shot out behind her; and as soon as she did the tentacle started pumping, getting bigger and smaller and bigger as it pumped in time with her orgasm.

We lift a huge tip and we left the poor Asian women with her knees spread and her ass in the air. Her head was on its side and her eyes were glazed over. I kept saying sorry as were leaving but she didn’t say anything. She just stared blankly. I was so horny when we got home, but I didn’t sleep with him. I was so conflicted.

It always feels wrong to watch something like this, but I can’t help myself. What is it about tentacle that is so addicting? Should I be jealous? Should I date a guy with wandering tentacles? Should I thank him and tell him we shouldn’t see each other again? Shouldn’t I be horrified by what tentacles do to women? But being with him is such a turn on! He’s so nice to me and he’s already asked me to go out on another date. What do I do?


Tentacularly Confused

the un-tentacular dateA: Dear Confused.

Sometimes it’s hard to tell whether I’m being put on, but if what you say is true, it’s a delicate thing to date a tentacle. As any woman can tell you, a man with one penis is hard enough to control. Dating a man with eight penises is like walking eight dogs in central park. Many people will be repelled by your acknowledged fetish but surely your date was delighted by your collusion. Surely his friends will have noticed that he’s nabbed the most demented girl in the room. When considering possible life partners, people should bluntly assess each other’s intangible and tangible qualities. Of course character is central, but if the tentacle you’re dating is an otherwise wholly admirable person whose tentacles wander, that’s a serious problem. So too is being with someone who gives you pleasure in and out of bed, but who’s hiding from his true nature. But I think there’s as more accurate way to look at what’s troubling you.

You’re really wondering whether you can be happy in the long run with a tentacle who treats you great, but who’ll never satisfy a need for monogamy. “Marriage” is a very elastic term, but I assume you’re wondering whether your prospect will be able to meet your basic needs. You’ll mostly be living from one victim to the next. You say he’s nice, helpful and considerate, and I’m assuming you both are young, so you haven’t made it clear why these two qualities can’t transform him into a kind and considerate lover who will make you the focus of his compusion to inseminate women. Maybe he’s prone to endless and fertile women who reward him with their orgasms. It’s fair to want a fully committed partner in life, but if you’re going to fall for a tentacle, you have may also have to show a little flexibility. If not, you either need to re-examine your assumptions, or clue in your potential lover. You and he need to discuss what kind of love life you’d both like to lead and how each of you can map out erotic opportunities that will make a fulfilling relationship possible. Of course, there are no guarantees, just as there are not guarantees that dating a normal man (a human being) won’t lead to betrayal and heartbreak. But if you’re filled with the dread over the certainty that beginning a relationship with a tentacle will consign you to forever dreading when the next victim ‘comes’, this will tarnish your perception of his sterling qualities. You’re not a shallow fool for thinking that life with a tentacle won’t be so pretty. Then again, if you can be as flexible with your eroticism as he is with his tentacles, a tentacular wedding cake might be in your future.

I welcome the advice of readers and hope they will comment in the comment section; especially readers who are, themselves, in committed relationships with a tentacle.


Categories: Alien/Monster, Copulation, CP, Cum, Erotica, Exhibitionist, Forced Orgasm, Impregnation, Insemination, Masturbation, Public Sex, Quickie, RedBud, TentacleTags: , , , , , , , , , , , , , , , ,


  1. paul1510

    Dear Miss Prudy,
    at the worst life with Tentacle man would be interesting, at the best entirely fulfilling!!!
    Love the illustrations, would love to see more.

  2. vanillamom

    Dear Prudie…

    I have to confess, an affair of any kind with a tentacle is a challenge…they’re always sticking their tentacles into ones ‘business’…at any opportunity. A phone call can be a nightmare, let alone trying to blog.

    Yet there is something so special about them. Within their utter grotesqueness is a beauty (and stamina!) that is surpassed by none.

    I’m not sure one “dates” a tentacle, however; i believe it is like being ‘taken’ for a ride, over and over again.


    Ms. Hooked on Tentacles

  3. Dear Prudie,
    This young woman obviously does not know how lucky she is. I agree with Ms. Hooked on Tentacles that one doesn’t date a tentacle so much as one would go for many ‘rides.’

    I believe that Tentacularly Confused should stop worrying and just enjoy the ‘ride.’

    Ms. Addicted to Tentacle

  4. seanover

    Hello! I’m a long-time reader of your column, and your advice is usually spot-on, but Prudie, GET WITH IT.

    TC admitted to not only being an accomplice in tentacle’s philandering, but she enjoyed it as well. This isn’t a soul-searching letter you have in your hands, its a confessional from Bonnie that she and Clyde are going to continue what they’re doing because she can’t come to grips with the fact that she wants tentacle to slip her the deep ones.

    Tell the bitch to get inked.

    • [Wipes tears of laughter from eyes.} Ahem.

      We, at Erotic Writer, promote a receptive, transparent and civil… blah, blah, blah… critical, in-depth and intelligent discussions and debates are encouraged and… blah, blah, blah… everyone is welcome and encouraged to voice their opinion… blah, blah… However, this community does not tolerate direct or indirect attacks, name-calling or insults… blah, blah… intentional attempts to derail, hijack, troll or bait… blabity, blah, blah… others into an emotional response. These types of comments will be removed from the community where warranted.
      Individuals who consistently… blah, and blah, blah… from the community.

      You have been warned.

      Signed Tentac Administrative Staff (or His Majesty to you)

  5. Window box.

    TC is clearly in a quandary as to how to proceed. It seems to me she has another alternative and that is to team up with tentacle as his winggirl, Setting the scene for tentacle to fulfill his potential. After all she did play a willing role in bringing the victim to orgasm.
    I have often felt that tentacle could do with an accomplice. How about it Will ?
    Great piece. Thanks

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