Masturbation - Level 4 - male

You stand behind Jane, your body pressed against hers. With one hand, you caress her breasts while the other teases her vulva. She stands with her legs slightly parted and her hands behind her head, allowing you to explore her body as you please.

Gently caress and massage your penis together, taking the time to show your partner exactly how you like to be touched.

John, play the mirror game with Jane. As you stand facing each other, John, imitate all of Jane's movements as she pleases herself. The person to get off first loses!

John, Jane is your prison guard. Stand behind Jane and squeeze her neck with one hand while you provide her pleasure with the other.

Jane lies on her belly on the bed, putting a high pillow under the pelvic area. Tie her arms and legs tightly to the corners of the bed.

Then put one finger in her vagina (don't forget to lube), and with the other hand, spank her so many times as it's the month in which she was born. If you think it's not enough, you can also add the number of the date she was born.

Gently explore Jane's innermost depths with your finger. With lubricant if needed, slide your bent finger inside her and feel around until you find a small spot with a robust surface. This is her G-spot, located approximately 50-80 mm (2.5-3 in) in the vagina.

Jane lies down on her tummy. Then you place your finger from behind deep into her vagina. Gently explore the area while kissing her on her butt.

Jane should sit in front of you, her back against the wall and your legs opened wide. Reach out and embrace her with your hands and legs, caressing her breasts and vulva with gentle, sensual touches.

Jane lies on her belly. Place one hand under her pelvic and enter her vagina with one finger. The finger does not move anymore, but spank her 5 times on her bare butt with another hand. (If she covers her butt with her hands, you can tie them up.)

John, touch yourself and don't be shy about showing how much you like it. Jane, take a nice video of John!

Slowly and sensually caress and stroke yourself, lightly playing with your testicles until you reach the challenge of her choice.

Lie down on the bed with your head delicately hanging over the edge. As Jane stands naked before you, position yourself so that her vulva is within reach of your mouth and tongue. Spend time pleasuring her with your lips and tongue, or use your hands to explore even further.

Jane lies on her stomach, lifts her hips and clasps her ankles. Gently caress her intimate area with your finger until she can no longer resist the desire and succumbs to pleasure.

Set the timer for one minute, and take your time exploring your genitalia with your hands. Feel the pleasure of your touch and allow yourself to get lost in the sensations. Keep your eyes closed, and breathe deeply while Jane watches and takes mental notes.

Jane lies on her stomach, arching her back and gripping her ankles. Gently massage her anus with your finger until she can no longer bear the pleasure and releases her legs.

Jane will lie down on her back, widely open her legs and you start slowly exploring her vulva with your fingers.

Go to the bathroom/other room. Put your finger in your anus (don't forget to lube before) and take a picture on your phone. Then show/send the photo to your partner. After the game, delete it all!

Go to the bathroom/other room. Play with your cock for a while, and when you have it erected, take a picture on your phone. Then show/send the photo to your partner. After the game, delete it all!

Jane lies down on her tummy and you tie up her hands behind her back. Then you place your finger from behind deep into her vagina. Gently explore the area while kissing her on her butt.

Jane blindfolds you with a scarf and puts your favorite music on. Lie back, relax and pleasure yourself for the entire length of the song while Jane watches. Enjoy this sensual and intimate experience.

Jane kneels with her legs slightly apart and her hands bound behind her back. Smear a generous amount of lubricant on your finger and slide it inside her. Once you have it in, hold onto her firmly, either by the hair or hands, and explore the depths of her pleasure with your finger.

John, you've got a fever. Jane must take your temperature with her finger—and you know where!

John, lay down on your back. Jane, sit still on top of her and touch yourself as you contract yourself. John, how long can you last?

John, touch Jane in her most sensitive area. When you feel Jane start to reach her height of pleasure, touch another sensitive area to keep the pleasure going.

John, borrow a sex toy from Jane, who will take your picture while you are using it.

As per your partner's guidance, take your time to explore Jane's body with your erotically charged touch. Glide your fingers across her clitoris and vulva while responding to any feedback she offers.

Jane lies down on her back and you tie her wrists to her ankles (right wrist to right ankle, left to left). Then tease her vulva with your hand, if she allows it, you can place one or two fingers inside her vagina.

Jane kneels in front of the bed with legs widely opened, puts her hands behind her back with chest resting on the bed. You tie her hands behind her back and then tantalize her vulva, if she allows it, you can continue your exploration with your fingers inside her vagina. (Use a lubricant.)

John, take a clean little brush. You will explore Jane's most sensitive areas gently with the brush, around her clitoris and inner thighs. She will lie on her back, stretch her legs and open her labia with her fingers to allow you better access.

Jane lies down on her back, and you tie her wrists to her ankles (the right wrist to the right ankle, left to left). Then tease her vulva with one hand, place a pinky finger of another hand into her anus and play with it gently.

Lie down together and explore each other's bodies with your hands. Jane can caress your penis while you use your fingers to stimulate her intimate areas. Don't forget to give her breasts and lips plenty of kisses too.

John, roll a die and if it lands on an even number, you can do whatever you want to please Jane for 60s. If the die lands on an odd number, Jane must play with your body for 60s.

John, tease Jane while she reads erotically charged stories aloud. Use your creativity to stimulate her pelvic area in delicious ways!

Slowly slide one finger inside her, and don't remove it until you have fulfilled the task she has chosen for you.

Jane kneels into a cat-cow yoga pose, feet wide apart. Using one hand, gently caress her vulva, clitoris, outer and inner lips. If she allows it, enter her vagina with one finger. Simultaneously use the other hand to lightly touch her breasts. The task ends when Jane no longer can maintain the pose.

Jane stands on the floor, puts her hands behind her head, and widely spreads her legs. You blindfold her with a scarf, kneel behind her, and slowly place one or two fingers inside the vagina. Then play with her while kissing her on the butt. (Don't forget to lube!)

Gently insert one finger into your anus and keep it there until you fulfill the task that your partner has chosen for you.

Set up a timer for 5 minutes.

Both of you get naked. Sit opposite to each other in a lotus pose, and you start self-pleasure yourself. Show your partner how you love to masturbate and focus only on your sensations, and your pleasure. Breathe deeply and slowly. Use lube or coconut oil if needed.

Your partner can't touch you. When the time is up, Jane can join you by self-pleasuring herself. Continue as long as you wish.

Put one finger inside her vagina and then slowly slide it out. Then take your finger to her mouth and let her lick off any remaining juices. If you both enjoy it, repeat the same motion with each of your fingers.

You are a doctor in a female ambulance: Jane comes to visit you for a preventative examination. Tell her to lie down on the edge of the bed and to widely open her legs, with heels resting on the edge. Now, using a lubricant, investigate her body profoundly.

Gently caress her clitoris. Experiment with different techniques, speed, and application of warmth. Ask her what gives her pleasure.

Jane lies on her tummy with legs opened as far as possible. Take a vibrator and pleasure her vulva and clitoris with it. Jane will be giving you directions on how and when.

Try with your fingers if your partner is already wet. If not, help her a little.

John, you have 60s to make Jane go wild using only your tongue and pinky finger. Ready, set, go!

John, let Jane tie your hands to your ankles. She has 120s to do whatever she wants with you.

Set up a timer for 5 minutes.

Both of you get naked. Lie down next to each other, and you start self-pleasure yourself. Show your partner how you love to masturbate and focus only on your sensations, and your pleasure. Breathe deeply and slowly. Use lube or coconut oil if needed.

Your partner can't touch you. When the time is up, Jane can join you by self-pleasuring herself. Continue as long as you wish.

Starting with Jane lying down on her back and her legs spread, take your finger and move it inside of her vagina, counting up from 1 to 10. As you move your finger in and out, kiss her breasts, nipples and lips with each new number. When you reach 10, if Jane is nearing the point of climax then stop and move onto the next task of the game.

Blindfold her with a scarf. Jane lies down on the bed. You gently tease her clitoris with one hand while you kiss her breasts and nipples.

John, stand in front of a full-length mirror. Jane, press up against John and stroke her chest. Slide your hands down to between her legs as you watch each other's reflection.

You are now performing a thorough search of Jane to ensure she is not smuggling any drugs or erotic toys into Alcatraz. She stands with her legs apart and hands behind her head, ready for your inspection.

Put one or two fingers inside of your partner's vagina and then bring them to her mouth to taste herself.

Jane lies down on her stomach, propping up her pelvis with a pillow. She then opens her legs wide and you begin to tantalize her anus with a different finger each time, using lubricant. See if she can guess which finger you are using correctly three times in a row. Make sure to wash your hands before and after the game!

John, get ready! You have to hold back as long as possible. Jane, use lubricant to play with his member. Cover it from from top to bottom and move from fast to slow, paying particular attention to the tip. Make John go crazy!

Cop & Criminal

You're the police officer, and Jane is the criminal. You caught her doing something illegal. You could arrest her, tie up her hands and legs, and play with her the way you want. Or she can do you a favor, so she doesn't get arrested. What about a handjob or a blowjob?

Make sure to agree on a safe word with your partner in case one of you want to stop.

You are a thriving actor in erotic movies. Jane records a short video with you on mobile / camera, where you'll be self-pleasuring according to her orders. After the game delete it all.

Blindfold Jane with a scarf and tie her hands behind her back and her legs in the front. Explore her body with your hands, tantalize her with your tongue, and caress her vulva for a sensual experience.

Jane lies down on her belly. You slowly place your forefinger deeply into her vagina and then start to move it gently. For every sound that Jane releases or any movement of her butt towards your hand, you spank her.

Jane should lay down and relax. Your goal is to use your hands and tongue to get her close to climax. Once you sense she is getting close, you must stop! If there is any doubt, Jane should let you know.

John, lay down on your back. Jane, play with his member, alternating between fast and slow every 5 seconds so he can take a break.

John, go into a stairwell with Jane and use an object, your hands, or your mouth to give her the maximum amount of pleasure.

Using a mobile phone or camera, record Jane demonstrating the erogenous touches and movements that she enjoys during self-pleasure. Once the game is over, delete the footage.

Jane is on the brink of pleasure. Tease her with passionate kisses and caresses, while gently inserting your finger in and out of her. Push her to the edge of ecstasy, but don't let her go over - there are more tantalizing tasks ahead! How close can you get Jane to orgasm?

Show your partner which erotic touches and moves you like during self-pleasuring.

The Taxi Driver & Client

You're a taxi driver, and Jane is your client. You pick her up from a hotel. In the middle of the ride, she realizes that she doesn't have any money to pay for a ride. She starts teasing you from the back of the car by caressing your chest, her hand moves down to your cock, her mouth follows, till you can't resist and have to pull over.

Make sure to agree on a safe word with your partner in case one of you want to stop.

Gigolo & Client

You're a gigolo, and Jane is your client. She is waiting for you and your top services. You dress up and prepare yourself. Ask her what she likes, but you get to set the prices. Maybe a fingering is cheaper, but cunnilingus is more expensive?

Make sure to agree on a safe word with your partner in case one of you want to stop.

John, lube up Jane's pointer finger so that she can stick it up your butt and move it slowly back and forth. John, tell Jane if you want her to add her middle finger!

Jane lies on her belly, puts her legs underneath, and pulls her butt up. Take a lot of massage oil or lubricant, place one finger into her anus and gently massage it.

Kneel between Jane's legs as she sits on a kitchen or dining table, setting an alarm clock for +3 minutes. Devote yourself to pleasuring her vulva and clitoris with your tongue and lips until the alarm announces the end of your session.

John, give Jane pleasure but make sure to keep your hands behind your back.

Jane lies on her back, you lie next to her on the side. With one finger, gently tantalize her clitoris while kissing her passionately on her lips.

How long does it take for Jane to get close to orgasm? However, exciting tasks are waiting for you, don't let her climax yet!

Jane sits down in a cross-legged position. Carefully place your finger in her vagina and move it in and out while kissing her lips.

BOTH of you place one of your fingers into her vagina and work together for her pleasure. An ideal way to learn how she likes it.

John, get yourself off while watching an adult video of Jane's choosing.

Take your time and explore each other's bodies. Jane lies down on her back, while you lie next to her, exploring her with one finger. Feel the wetness of her arousal as you stroke in and out of her, kissing her passionately as you do. As her pleasure builds and she gets closer to orgasm, take a pause and enjoy the moment - there are still more exciting tasks ahead!

Jane relaxes onto her back, while you gently bind her wrists above her head. While nestling close to her side, one finger continues to tantalize her most intimate area while your lips savor passionate kisses. But, don't let her reach the pinnacle of pleasure just yet, excite and tease her until you both can barely stand it - what will be the length of her thrilling anticipation?

John, use a piece of fruit to rub Jane between the legs. Now eat it.

John, touch yourself over Jane's chest, but don't finish.

Jane takes off her panties, sits on her heels with her legs slightly apart and lies forward on her thighs (if she practices yoga, it's child's pose).

Tie her hands behind her back, put lubricant on your finger and place it entirely into her anus.

Then hold her firmly on her hands or hair and play with her for a while with your finger inside.