Threesome – Step by Step


You may think the hardest part of having a threesome is finding the perfect person to join in your couple’s sex life, but it’s even harder to handle all the emotions involved, namely jealousy and insecurity. So what’s the best way to go about it?

First, know the reason. You need to figure out as a couple why you want to try having a threesome. Is this his fantasy, or hers, or something you’ve both wanted to try together? Are you pushing your own limits to explore who you are sexually? Do you want to add a new, maybe bisexual, dimension to sex? Are you easing into the concept of sharing your partner or having group sex? Is this a purely physical/sexual experience, or a gateway to a ménage à trois/polyamory relationship? Whatever your reason, be aware that it won’t save a troubled relationship, as it invites hurt feelings, can do irreparable damage to a couple’s intimacy, and potentially leads to a love triangle that could tear the couple apart. Be sure you both want to do it. A threesome requires a high level of openness and trust to work.

Second, find someone suitable. Decide whether to choose from your close friends (such as sorority sisters you’ve already partied naked with), acquaintances (they’re probably sane, STD-free, approachable, and not a great loss if it doesn’t work out), or a total stranger (easier to find online, for a one-time thing, or to keep private from your social network), but not exes (due to their emotional baggage). Whether you pick another female or another male, make sure you both find her/him attractive, or it could hurt your sexual performance and pleasure. If they’re too attractive, you might need to deal with your own insecurities first. To entice the third person, you might need to coyly ask them out to put them in the mood. Make sure they’re ready, willing, and able to have sex with you as a couple, and you’re not making them jump through hoops or suffer delays as you vet them together, or they will lose patience and not take you seriously, and the threesome fantasy will not become a reality.

Third, set the ground rules and boundaries. Make sure all three of you provide input and come to an agreement on everything. This isn’t just for physical safety (doing it at a hotel for comfort and privacy, using separate condoms for various sex pairings) but also to protect your emotional well-being (communicating what you’re not okay with, who can/can’t kiss and touch, who can/can’t penetrate whom and where orally/vaginally/anally, and what three-way sex positions will make you feel left out). Figure out all the nitty-gritty details, any uncomfortable scenarios that could arise, and how to resolve them. Take this opportunity to imagine and describe all the wild positions and sexy things you can do with three bodies instead of just two. The more you discuss and plan beforehand, the more ready and eager you’ll be, and the more you’ll get out of this experience. If you’d rather be totally spontaneous, you risk unnecessarily offending someone, showing up with no idea what you should do with yourself, and having regrets later. To prevent any confusion, also plan how it should end, like taking a cab home afterward (to mark the end of the shared physical experience, so it’s not weird when you wake up). Figure out if the threesome should be a one-time thing or potentially ongoing.

Fourth, meet and progressively increase sexual tension. It might be easier to break the ice at a café or a lounge, with just one person of the couple initially meeting the third person, then flirting and complimenting them. This way the third person can feel safe in public, not feel like a third wheel, and can quickly build rapport one-on-one. If their chemistry together is good, the other person of the couple can join, and the first person of the couple can facilitate their getting to know each other, keeping the tone upbeat and humorous with light teasing. Everyone should divide their attention with the other two, with a focus on the less enthusiastic person, so nobody feels left out. From chatting, gradually increase skin contact and touching, like: stroking their arm, patting their shoulder, combing strands of hair off their face and tucking it behind their ear, and hugging. When everyone is physically comfortable with each other, and sexual tension is getting unbearable, they should proceed to a private room with a bed. Savor the foreplay. Circle each other, hold hands, gently but firmly rub up on each other, slowly undress each other, and give each other massages.

Fifth, maintain intimacy with your partner while having sex. The greatest danger in a threesome (after the physical ones of pregnancy and STDs) is jealousy and insecurity. A couple just focuses on each other with their full body, mind, and feelings. An orgy is a confusing tangle of body parts experiencing simultaneous sex from everywhere from anyone. But a threesome uniquely challenges intimacy in the constant threat of making one feel less desired or left out as the third wheel, so be attentive to both. Don’t let the novelty of a new third person get you carried away. You need to reassure your partner that she is still your focus, and this is all just a physical experience, not a relationship with the third. You don’t have to always be working on both people like in a game of Twister, but frequently touch or gaze at your partner. Be creative and spontaneous within the group’s guidelines, and always ask first if you want to try something they didn’t ask for so you have continual affirmative consent. If anyone’s ever uncomfortable and wants to stop, everyone should stop, and not rudely continue without them.

Sixth, follow up. Message the third participant the next day, so they don’t feel used and ignored but rather valued as an integral part of your threesome experience. You can decide whether to see each other again or just keep it a one-time thing (you’re not dating, after all). Hopefully everyone had an exhilarating, stimulating, mind-blowing experience that affirms your vibrant sex life together.

Stay tuned for the next article on threesome sex positions.



Anal Sex Advice (Continued)



How to Have Anal Sex by Nymphenomenal

This continues my previous post, “On Anal,” which covered: Considerations | Prep days before | Ready to start when | General arousal and vagina first | Anal tease | Use plenty of lube

Anal entry by fingering:

Anal sex should start slow and small. Slowly insert a lubed pinky finger into her anus. (Make sure his nails are short and smooth so they don’t scratch her inside.) If she can’t tolerate a finger in her ass, she won’t like anal sex. If she’s ready for more, you can work your way up with anal sex toys like butt plugs to gradually stretch open her anus. It may be uncomfortable at first, but it shouldn’t hurt. Stop if it ever starts to hurt! If she starts to bleed rectally, stop and wait until it fully heals before trying anal sex again. Done correctly, she may feel sore but she shouldn’t bleed. However, slight bleeding and spotting is very common, and usually clears up within a week. If it doesn’t heal in a week, or it hurts a lot, go see a doctor right away.

Anal sex positions for penile insertion:

If neither sex partner has tried anal before, the woman should start on top. If she has had anal sex before, you should start with her preferred sex position for anal entry. If he has had anal sex before, but she hasn’t, and she trusts and prefers him to lead, then he can start on top. Being on top gives her more control, though being on the bottom may make it easier for her to relax her anus. Try these four positions to get started on anal sex:

With her on top, try (1) the cowgirl position, so she can ease herself down onto his penis and go at her own pace. When she’s ready, he may flip her over to a better position for him to thrust or do what he wants.

With him on top, try these positions, from least to most uncomfortable for her: (2) lying face-down flat on her stomach (with her butt up), then (3) doggie-style position (with her butt out at him), and then (4) missionary position (with her lying face-up on her back, with her legs tucked up to expose her butt).

Anal technique, pumping, and sensation:

GO SLOW! Even if she’s aroused, relaxed, and lubed up, she may still feel a lot of discomfort, so he should be patient and go slow for her. Her anus may be very slippery and feel very good so tight (especially compared to the vagina), but he should control himself to enter gradually and carefully, especially if it’s her first time ever trying anal sex, as accidentally slipping in can be traumatic for her.

Insertion of the whole tip of his penis may be the most uncomfortable for her, as it stretches open her anal sphincter up to the size of his shaft. Slowly dip his penis in and out of her, starting with shallow thrusts and slowly pumping in his penis a little deeper every time. Whenever his penis slips out of her anus, be careful to reinsert it without touching her vagina, to avoid introducing fecal germs into the vagina, and to avoid spreading fecal matter that could stain your bed sheets. His angle of insertion can also hurt her if the angle is too sharp. She might feel slightly sore from anal stretching at first. As his penis goes deeper into her anal canal toward her rectum, she may feel like she’s pooping, though she isn’t pooping. If she enjoys taking a good dump, she may find this sensation very pleasurable. After a few minutes, her anus should feel adjusted and relaxed, and then she may find it comparable to vaginal sex but in an adjacent bodily cavity. It’s a thin wall between the anal canal and the vaginal canal, so your dick could be indirectly stimulating her g-spot on her front vaginal wall. Some women can even orgasm through anal penetration, especially with simultaneous stimulation (of her clitoris, vagina, mouth, and skin/whole body). Note that men who are anally penetrated can have their prostate stimulated and massaged, which is not only pleasurable but also healthy, as it deters prostate cancer. Best of all, the man penetrating can cum in her anus without the risk of pregnancy (though anal sex still risks transmitting STDs, plus anal warts and anal cancer, plus fecal infection, so condoms are still highly recommended).


After he cums and finishes in her anus, his penis (or his condom sheath) will be covered in fecal germs (invisible) and also possibly some poop (visible). This is harmless as long as: the used condom is thrown away, and his anally inserted penis is immediately washed off with warm water and soap (and NOT reintroduced into a vagina!). Remember to never reinsert anal probes back into a vagina without first cleaning up and at least putting on a new condom!

After sex, she should cup under her genitals on her way to the restroom, in case his cum drips back out of her. Like for vaginal sex, she should immediately pee to avoid UTIs. She should queef any air pumped into her vagina and/or anus, try to drip out his cum, and possibly even poop. Remember to only ever wipe front to back (never back to front), due to fecal germs! Even better if she can also wash the area with warm water and soap or take a shower.

Note that she may feel a bit sore, and even bleed or spot a bit, which are normal, shouldn’t hurt, and should go away within a week. However, if you: have heavy bleeding, are hurting, feel like you have a tear or cut, feel itchy, or have sores, lumps, or unusual discharge, see a doctor as soon as possible, in case you need to clear up an infection. Make sure the issue is gone, she’s not spotting, and everything is back to normal before you resume having anal sex.

Keep in mind that anal sex may be uncomfortable but should never hurt! A woman may not enjoy it her first time or two, as her anus may need to be stretched out (like a virgin’s hymen may need to be torn from the first few times she’s been vaginally penetrated). But, if after a few tries, a woman still finds no pleasure in being rimmed, fingered in the anus, or having anal sex with you, then anal sex probably isn’t her thing. Then you should stop suggesting it, but give her plenty of credit for having given it a shot and trying something new to spice up your sex lives. Here’s hoping you both discover the joys of anal sex! –Nymphenomenal


Nymphenomenal: On Anal


Sex through the back door has a reputation for being one-sided: fun for men penetrating, but not for women penetrated. This misconception comes from women who have had bad anal sex experiences, most likely from her man: pressuring her into it, not using enough lube on her, and not going slow enough to minimize her pain while maximizing her pleasure. For anal sex to be good, you both have to want it, be prepared, and trust the penetrator to be careful with your anus to avoid pain, injury, and infection.


Pros of anal sex: better for smaller penises, tighter than a vagina, edge of anus full of sensitive nerve endings, different feel than the vagina, women and men both have anuses, and he can cum inside her without the risk of pregnancy.

Cons of anal sex: may be more uncomfortable than pleasurable, can cause rectal tears and bleeding, can still get STDs (same ones as vaginal sex, plus anal warts and anal cancer), and can also get fecal germs, infections, diarrhea, and bloody stools.

Prep days before:

Men planning to have penetrative sex should: keep up their cardio (like running) to build stamina, keep hydrated (drink water instead of alcohol) to get it up and finish, and refrain from masturbating (in the days before sex) to prevent wearing out and desensitizing the penis.

Women planning to be penetrated anally should: stay hydrated and eat plenty of fiber (like fruits and vegetables) for healthy regular bowel movements (anywhere from every 3 days to 3 times a day), not hold in her poop (to avoid constipation), and not strain when pooping (to avoid causing fissures or small tears in her colon, as well as pushing her colon out).

Ready to start when:

Men should provide: towels (a large one to have sex on, and a small one to wipe away sweat), condoms (same type but use separate ones for anal and vaginal), baby wipes (to clean up his penis and balls), and lube (plenty of it, with a lube shooter/launcher if possible). If no lube, make sure his saliva isn’t contaminated, by cleaning his mouth of sugar and spicy residue, and keep hydrated (drink water).

Women: should not be currently feeling the urge to poop (can have just pooped), so the anal canal should be clear (poop is stored further up the colon, though fecal bacteria are still present throughout). She should have a clean outer butt (just showered, or wiped to the rim clean with water), but can do an enema (if she’s feeling self-conscious about her poop residue, or if he also plans to rim her with his tongue). Like the vagina, no hair waxing is necessary. She should not have any anal bleeding or spotting when she’s about to start anal sex.

General arousal and vagina first:

The woman should be very aroused and relaxed when she’s penetrated. So it helps to start with foreplay, stimulating her clitoris, and entering her vagina to build her up. When she’s ready, then he can start entering her anus.

Warning: just like only wiping your genitals from front to back, you can only go from vagina to anus (never anus to vagina)! Don’t let any finger, sex toy, condom, or penis that has been in the anus enter or even touch the vagina again without first being washed (with warm water and soap) and sanitized (disinfecting sex toys in boiling water). This is because even if you don’t see any poop residue, the anus is full of germs and bacteria that can wreck havoc in the vagina, causing vaginal and urinary tract infections. Rectal bacteria can also infect the inserted penis (through the open tip, or weakened skin), so it’s better to wear a condom (even if you’re monogamous without STDs). It’s best to try anal sex at the end before cleaning up after sex, but if he really wants to reenter the vagina, first wipe the sex toy or penis and balls thoroughly with baby wipes, then put on a new condom, before reentering her vagina.

Anal tease:

Her man should start by teasing the edge of her anus, which is full of sensitive nerve endings and where the erotic sensation is. He can even try licking and tonguing the rim, called rimming.

She should try to relax her anal sphincter, which is the round muscle at the edge of the anus. It tightens to hold in poop, and needs to be relaxed to open. Relax like she’s going to poop, but without pushing out any poop (don’t worry, no poop should come out). She doesn’t want to loosen her anal sphincter by getting penetrated when it’s closed tight, which could be painful and difficult. If it feels loose, she can strengthen it with Kegel exercises (which strengthen pelvic floor muscles, and also help with urinary incontinence and childbirth recovery). She should also consider the girth size of her poop logs. That’s the size her anal sphincter comfortably stretches to. If her man’s penis has more girth size, she may want to practice with fingers and anal toys (like butt plugs) to work up to his size.

Use plenty of lube:

Unlike the vagina, the anal canal has fragile walls and lacks natural lubrication, making it very susceptible to tearing and infections. Thicker water-based lubes (like KY Jelly or Durex) are best, as they: don’t dry out as quickly, work well with condoms, and clean up easily. Oil-based lubes (like Vaseline or Crisco) are less good, as they: weaken latex condoms, and are harder to wash off afterwards. Saliva is a last resort (say, if you run out of lube), as it: isn’t as slippery, dries out quickly, and can cause irritation if contaminated by certain foods. Saliva itself is totally safe (assuming you don’t have STDs), especially if you just brushed your teeth and used mouthwash. However, if he just ate or drank sugary stuff, his saliva in her vagina can increase her likelihood of getting a yeast infection. And if he just ate spicy food, his saliva in her anus can cause a slight burning sensation for her anus and for his inserted penis.

Whatever you choose, make sure her anus is well-lubricated. Before penetration, you can slowly squirt lube in (with a lube shooter/launcher), to pre-coat her anal canal. At the least, lube anything before its insertion, to help it glide in.

Check out my next upcoming column, which will cover: Anal entry by fingering | Anal sex positions for penile insertion | Anal technique, pumping, and sensation | Cleanup



How To Get A Female To Orgasm

146446519830450 Artwork by Ketza

How To Get A Female To Orgasm

If your exposure to female sexuality is limited primarily to pornography, you might get the impression that women just need to touch a big hard dick to get aroused to orgasm. But we all know in reality that most women are much more complicated than that.

Compared to women, most guys are pretty straightforward. They see a sexy body, they quickly get horny, their dick gets erect, they pump their dick, and they orgasm with a squirt of cum. That’s the usual pattern when they masturbate or have sex. Their main goal is to orgasm, and their secondary goal is to get their partner to orgasm.

Women, on the other hand, don’t really fit a single pattern. Some arouse quickly from touching a sexy body, while others arouse slowly from building an emotional connection over a deep conversation. Some women are always horny and wet, while others seem to never be in the mood. They may prefer deep vaginal or anal penetration, firm oral or clitoral stimulation, or just a tight hug and slow full body massage. They may hope for multiple orgasms or expect none at all. So when a guy initiates sex with a new woman, how does he get her to orgasm?

First of all, realize that although women like to orgasm as much as men do, many women have difficulty reaching it, and some just don’t orgasm. But that doesn’t mean you shouldn’t try anyways, because she still might orgasm, and at least she’d enjoy your seduction. If she doesn’t orgasm, don’t take it personally as a failure, because it may be nobody’s fault, and that will totally ruin the mood.

Unlike the male orgasm process which is mostly visual and physical, the female orgasm process is more mental than physical. In a penis-in-vagina scenario, the guy will feel good mostly from the physical act, but the woman will only feel good if she’s in the mood. Try to put her in the mood by making her feel sexy and desired. Tell her you want her now, but you can wait until she’s ready. That way you tempt her without pressuring her, so she feels safe and in control. Also try to make her feel respected, relaxed, comfortable, and warm. Skin contact is very telling. If she avoids your touch, she doesn’t want to have sex with you. If she likes it and wants more, you should keep pushing the boundaries until she stops enjoying it or tells you to stop there for now. Take full advantage of foreplay to get her aroused and wet for you

When you start having sex, ask her what she likes and wants from you. Even if it’s weird, don’t mock her, and try to deliver. She may be able to build an orgasm only in a certain way, be it: a specific sex position, prolonged amount of pressure or motion, simultaneous stimulation of various parts, having rough or kinky sex, or using vibrators or toys. Most women also need to visualize horny thoughts, which could be aided with dirty talk, acting out scenes, and props, or just hearing your heavy breathing and wordless moaning. If she doesn’t state any preferences, take control and proceed with how you want to have sex with her, and switch out anything she dislikes to something else she might enjoy.

Try to help her reach orgasm before you do, as she might need your dick to be erect, though she might not need it at all. Try to last as long as possible, in order to pleasure her, not just so you can brag about your stamina. If she orgasms, keep trying to give her more orgasms. If she doesn’t orgasm, keep trying to help her until you’re too tired. If you orgasm first, or your dick goes limp, keep trying to build up her orgasm by stimulating the parts she’s focusing on. You may need to replace your penis with your hands to apply pressure to her clitoris and your fingers to throb her vagina. There’s no excuse for you to stop until she’s had enough or you pass out from trying. After sex, most women enjoy cuddling or being spooned until they fall asleep in your arms. This is important for building that connection so when she wakes up she’ll want to have sex with you again.

Most importantly, keep in mind that women have a different goal than men when it comes to sex. Her goal is for you both to enjoy the experience—both the physical sensation (having sex) and the emotional connection (being in the mood, being intimate together, you trying your best to pleasure her)—which hopefully lead to orgasm but often don’t. In the end, it’s more important that she felt sexually pleasured the way she wanted you to than for her to have simply orgasmed. And making her happy increases your odds for having sex with her again.


How To Do Me Properly by BaBsTyLe

    Have you ever had sex so good that it made your dick hard thinking about it? Now, you might think I am freak and that’s okay because I am. Everyone has a little freak in them and I know I am not the only one that gets wet from thinking about how good I was fucked. I am not any sex expert, but I know what I want, need and like. I had my fair share of addicting sexually pleasure that would make me phene for more and sex that was so bad, that I wanted to kick my own ass for allowing me to let him waste my fucking time.
    There’s a difference between getting fucked by a man and getting fucked by a boy (18 years old and up). Age is not a factor, just because you think of yourself as a man, doesn’t mean you know what the fuck you are doing.  A man takes the time to learn your body, knows how to handle your body and will wait until you are completely orgasmed out before he cums. Where as a boy is usually fucking a woman with no plan, no sense of direction, and would orgasm before her. He might even hit you with that, “I’ll get you next time.” If you are not able to get rock hard after 10 minutes to finish her orgasm, then you should take yourself and your little man out the door and don’t come back.
    Women love when a man is able to satisfy her, I know I do. I am not for a second saying that pleasuring your partner is a one-way street because both people should take the time to learn and teach each other their pleasurable ticks. I know I am dealing with a man when I am thinking about how he fucked me makes my pussy soak and when I want to talk to him about how he was handling me so well. Sometimes if I have been fucked right, I can feel the penetration as I am thinking about it. When a woman is getting good dick, she doesn’t want to fuck anyone else but him.
Turn on/off for me and many women. Turn on, when a man washes his body and ass correctly, because there is nothing more gross then a women witnessing your shit stains on her clean blankets after she just slopped down or fucked your hard cock. A man knowing how to foreplay is a big turn on for many women, it’s the warm/ build up.
First, have fresh breath, because she might like to kiss. The main kissing points that gets me wet when it comes to kissing is lip pressure, meaning the pressing of both lips firmly against each other, but not causing pain. When he pulls me into his body tightly but gently while he is kissing me, feeling how horny he is and his hard dick against my body lets me know how bad he wants me. Regular kissing can get the job done if that’s what she likes, but it’s a plus when the man knows how to French kiss without causing pain,  breaking her teeth, eating her face, assuming that she is thirsty and providing lots of his silaba for her to drink.
    Great French kissing to me is when he is able to follow my lead (tongue) or being able to guild me. The move that gets me wet all the time is when he bits my bottom lip, it’s sexy as fuck and turns me on. A little pain feels good when I am horny. Bitten too hard is not good and you don’t want to bite to cause irritation or bleeding, because that’s a turn off.  Biting too much can be a turn off, once or twice is good and when she is not expecting it.
    When a man is not scared to have her coochie dripping in his mouth, is a big turn on. I love it when a man asks me to sit on his face until he can’t breathe and to ride his fucking filthy mouth until my soaking wet coochie cum all down his fucking throat. Anyways, you have to figure out how she likes it, ask her to direct you or some women like me, will direct you while you are sucking and stoppering all over my clit.   It’s a turn off when I say, “right there”, “that feels good”, “don’t stop” , I am moaning and the guys stops what he is doing and start doing something else. This do not only frustrates me but frustrates a lot of women, because we have to start building up our orgasm again and sometimes the man can’t always find that sweet spot again as quick as it was lost.
    When a man knows how to talk dirty to me while he is fucking my little tight bald wet pussy with his big swollen cock real deep and firm. He whisper in my ear, “Bitch, you are mine to use, you are my cum whore.” Sometimes I am in a sluty mood and that’s what I need and usually it makes me orgasm a lot quicker. You have to know her moods and what type of sex she is wanting or need at that time. –BaBsTyLe