FREQUENTLY ASKED QUESTIONS
How did you get into ass-play with men?
How did you end up doing this website?
How long have you been doing this?
Why are you interested in this?
Do you have a girlfriend or boyfriend?
Who do you like more, men or women?Why my butt?
Doesn't ass-fucking hurt?
Does wanting this make me bisexual or gay?
What is prostate milking? What is prostate massage?
Do I need to clean internally to prepare? Should I give myself an enema?What to (and Not to) Expect from a Session
How should I address you?
What do I need to do before we can schedule a session and meet?
What might happen during an ass-play session?
Are you an escort? A “full service” or oral provider?
Will you jerk me off?
Don't you want to make me cum?
So can I cum without touching my cock?
What if I discover, or already know, that prostate stimulation doesn’t feel pleasurable to me?
Can I cum more than once in a session?
Do you have a favorite dildo?
May I pleasure you?
Do you enjoy fisting?
May I buy you presents? Where are your wishlists?I’m a dominant man; would I still enjoy this?
I’m a submissive man; will you dominate me?
Will you dominate me verbally?
Why don't you call it “training?”
Do you play with women too?
Do you offer services for couples?
Miscellaneous FAQs (including "Where are you located?")
How did you get into ass-play with men?
When I was an undergraduate at MIT, my friend asked me to take her shopping for a harness to use with her boyfriend, because I was the kinkiest friend she had. Her boyfriend was already into ass play, but she needed a harness for the toy he wanted to use, which was not small. She bought a harness and, for her birthday, I bought her the instructional video Bend over Boyfriend under the condition that I could watch it before I gave it to her. I watched it, and found it informative, but didn’t feel compelled to start fucking guys in the ass with my strap-on (that I used occasionally with women). When my friend ended up marrying aforementioned boyfriend, I gave them a His and Hers matching dildo and butt plug set.
Two years later, when I was getting my master’s degree in social science research, I hooked up with this one guy who just went wild when I started playing with his ass. He was so into it that eventually I had practically my whole hand in there, and, over the course of several hours, he had five orgasms without ejaculating, each one lasting forever, with rolling waves of pleasure. I thought: “GODDAMN! I need to do more of this! I need to learn how to harness (pun intended) this powerful mojo.” So I read The Ultimate Guide to Anal Sex for Men and “practiced” whenever I hooked up with guys who already knew how much they loved ass play. “Practicing” was fun!
How did you end up doing this website?
When my fiance and I broke up, I went on AdultFriendFinder. My profile there said explicitly that I was looking for really hot, G.Q. or Abercrombie & Fitch-looking, tall, muscular dominant men who already know how much they like having their asses played with. I got a ton of responses—many more than I expected—from attractive "normal" guys who already enjoyed ass play. I hooked up with many of them. They would say to me afterwards, "I've never had it done properly like THAT before!" which made me realize that I had quite a talent for it. I felt it was a bit of a shame that only hot dominant guys got to experience my talent, so when I found myself without a job, I decided to make this more widely available by charging for my time. I'm much happier now than I was as a statistician. Now I spend my whole day talking about and having ass sex instead of trying to pretend that I am vanilla and "normal" in a 9-to-5 job.
How long have you been doing this?
I've been playing with men's asses since 2002. I made my talent more widely available in April 2007.
Why are you interested in this?
When the chemistry is right, I do enjoy the power exchange / role reversal, but more than anything, I love giving such intense pleasure; pleasure that the people who visit me usually can't get elsewhere, and therefore makes them really appreciative. I like making you writhe on my hand (or cock) and watching you enjoy yourself. It can be tender and intimate, and intense. I like intense. I find it sexually satisfying to give people this much pleasure, in the same way that I find it sexually satisfying to perform extensive cunnilingus on a woman.
Do you have a girlfriend or boyfriend?
I have various playmates of all genders available for live sex shows with me sometimes, as well as two boyfriends who are not available for live shows. Don't ask me if you're my type and can get fucked for free; it's just insulting. And PLEASE do not send me (or any other woman!) pictures of your cock, however big and lovely it may be.
Who do you like more, men or women?
For what? For casual sex, I prefer men because men are (usually) easy and women are (usually) more difficult. For relationships, I like both equally.
That's how I get access to your prostate, silly. Also, you have tons of yummy nerve endings there....very sensitive.
Only if it is done wrong. And I do it oh-so-right.
Does wanting this make me bisexual or gay?
First of all, there is nothing wrong with being bisexual or gay! Heck, I'm bi! Yay, queers! That said, are you attracted to men? Then sure, you may be bi or gay. Not attracted to men, but just want a cock in your ass or mouth? Want the person to be putting the cock in your ass to be a woman only? You're probably not bi or gay. Also, transsexuals (TS) are women who have cocks. Wanting to be fucked by a trans woman doesn't make you less straight, just more kinky. Referring to transsexual women as "shemales" just makes you an asshole, despite the fact you see that offensive term everywhere online.
What is prostate milking? What is prostate massage?
For the most part, they are the same. Milking is mainly just domme-speak for prostate massage and alludes to the fact that, for some men, prostate massage can cause some fluid (often only a few drops) to come out of your cock without orgasm. Prostate massage is the male version of manually stimulating the female G-spot. In fact, some people call the prostate the “male G-spot” or the “P-spot.” Others know it as the spot that, when stimulated, makes a pleasurable tingling sensation go all the way through their cock. Not everyone responds to prostate stimulation in the same way. Some people enjoy light prostate stimulation, some enjoy very firm pressure, others find contact to be painful, and yet others only feel like they have to pee.
Do I need to clean internally to prepare? Should I give myself an enema?
Tristan Taormino (the anal sex for women guru) addresses this question very well, so I will direct you to her comments instead of repeating them here. She explains how, when, and why to do an enema as well as why, depending on the consistency of your shit, you probably don't need to do any kind of internal cleansing.
Her short answer is "if you have a bowel movement before you have anal sex, there should only be trace amounts of fecal matter in the rectum[...]provided that you are a relatively healthy person with a good diet, normal bowel habits, and no gastrointestinal problems."
Just “Jo” is fine. If you feel the need to use a title with me, I prefer the authority of “Sir.” Depending on the depth of our relationship, you might eventually be allowed to call me "Master.” But “Jo” is my preferred form of address. Call me “Mistress” or “Ma’am” at your peril, and not a sexy kind of peril.
What do I need to do before we can schedule a session and meet?
Follow the directions on the Contact page. I only schedule appointments after we do a phone screening, so please allow time for this process.
What might happen during an ass-play session?
To be clear, when you give me money, you are doing so as a gift in return for my time and companionship only. The acceptance of this money does not obligate me to participate in any type of activity. You must understand and agree that any money exchanged is for time and companionship only. Legally we cannot and will not discuss or agree to any type of solicitation. No fees or tips of any kind will be quoted, negotiated, assessed, or collected in exchange for sexual conduct.
The following description is of my fantasy and not contracted for informally or formally: When you arrive, I greet you with a big hug, during which your hands do not wander to my ass, and we synchronize our breathing, taking a few deep breaths together. You then take off your clothing and lie face down on my massage table (in Boston) or hotel bed (when traveling). I give you a regular massage and we chat, getting comfortable with each other, connecting. I'm great at deep tissue work and pretty damn good at less deep relaxation massages. After massaging the rest of your body, I massage your anus, on the outside. When you're excited and ready for more, you lie on your back with your knees bent, feet on the bed, and legs spread. I have on my panties only. I sit between your legs and put on latex gloves. I use lots of thick lube that cushions your sensitive ass skin. I caress the outside of your asshole. I then wait for your asshole to relax and let my one gloved finger in. I don't push my way in; I'm very patient and go very slowly. I require that you communicate clearly with me and let me know if it is even uncomfortable, not waiting for it to be painful. I want to make sure that it feels good the whole time. There is no "grin and bear it" with me.
After your ass lets one finger in, I massage your prostate, figuring out what type of stimulation your ass likes best, trying several different techniques including a vibrator. You might ejaculate at this point in the session and choose to wait until your next visit to experience my strap-on. You might have orgasms without ejaculating and, after a few minutes of relaxation, be ready to keep going. Most likely, you will feel pretty good but not have an orgasm at this point. Then, depending on what my fingers tell me about your ass, I choose which dildo to use in my harness. I get off on making it feel good, not on using as big a dildo as possible. (If you are interested in using increasingly large dildos, I can do that, but I suggest allowing for a longer session, so that it can be done slowly as your ass relaxes and expands naturally.) I then put on the harness with that dildo and sit between your legs again. I slide forward with my legs under your knees, my feet next to your torso. I enter you and slide in and out according to what feels best for you. It can be as vigorous or tender as you would like. After I become familiar with how your ass likes to be fucked and know that I am not hurting you, if you would like to, we can change positions to doggy style, you on top, or any other configuration. At some point during all of this, you can no longer keep your hands off your cock, and you finish yourself alone or with my help.
Are you an escort? A “full service” or oral provider?
I am not an escort in the traditional sense, but rather a "top-only" escort. I am not a “full service” provider. Additionally, I will not blow you, nor rim you, and only maybe will jerk you off by hand (See next question). You may finish yourself off while I take care of your ass.
Access to my asshole, pussy, nipples, or face/mouth is not available, so don't ask. Don't grope anywhere else on my body either...if I want to be touched somewhere, I will invite you to do so. Specifically asking is less likely to have the outcome you want than if you wait for me to ask.
When people try to get what I don't offer, it makes both of us uncomfortable.
Short answer: Maybe. Probably, but no guarantee. I may stroke your cock if it is hard and I feel so moved, but do not expect it or ask for it.
Long answer:
1.Jerking you off while fucking you is a little like trying to rub your belly and pat your head at the same time. It requires slightly more coordination than I have, and I prefer to do a good job fucking your ass than a half-assed job (so to speak) on both your ass and cock. The motions are not necessarily the same, and the two body parts often require different rhythms; it depends on the person.
2.Prostate stimulation tends to result in a limp cock. You may doubt that, but it is a biological fact. It happens to most guys (except in strap-on porn because they only hire guys who stay hard, not because all guys stay hard). It's not a failing of your manhood or anything. You can still cum with a limp cock, but it’s even more difficult for me to try to coordinate fucking your ass with working a limp cock.
3.I get off on giving you the most intense orgasm possible. I know how to work your ass just right for that. You know how to work your cock just right for that. Combine those two forces, and you will probably have a much more intense orgasm than if I fumble around with your cock.
Don't you want to make me cum?
Considering that most of the stimulation comes from what I do to your ass, I am making you cum; I’m just doing so via your ass. You have no idea how intense I get about it. I have a giant grin on my face the whole time I'm in your ass, from fingers to vibrator to strap-on. I figure out what movements and motions are most intense for you, and work you into a frenzy. I play you like an instrument, have you writhing on my finger or fingers.
So can I cum without touching my cock?
Some men can, but is it really that important a goal, when you might have a much more intense orgasm as a combination of prostate and cock stimulation?
What if I discover, or already know, that prostate stimulation doesn’t feel pleasurable to me?
I can help you discover what does feel pleasurable to you. You can still enjoy anal play because of the abundance of sensitive nerves in and around your asshole. Some people like feeling full or stretched, some enjoy the sensation of something moving in-and-out of their ass, and others like primarily external stimulation like stroking, licking (I don’t do this with you!), or vibration. For many people, the eroticism results from the psychological aspect of being penetrated or playing with a previously off-limits part of their body.
Can I cum more than once in a session?
If you often cum several times in a short time span, I recommend you choose a longer session. That said, almost everyone who asks me that ends up deciding after one really huge orgasm that they’re quite satisfied for the session, and all set. Some people discover with me how to have non-ejaculatory orgasms, of which you can sometimes have several before an ejaculatory orgasm.
In my private life, I usually use the red semi-realistic one that I used in my videos. It's definitely bigger than many of my other dildos, but it gets plenty of action in my private life, so I don't feel compelled to use it with you. Honestly, my favorite dildo to use on you is whatever one feels best for you; one that allows me to fuck you properly without causing any pain or stinging.
By entrusting your ass to me, you give me pleasure. You may watch me pleasure myself. But you may not touch my body without explicit invitation from me, which will never be an invitation to touch my genitals, asshole, nipples, or face with any part of your body. No, you can't pay extra for it.
I know that some of you reading this find the idea of fisting to be extreme and/or scary. Don't worry....I have no interest in fisting someone who is not comfortable with or prepared for this activity! However, I do get asked this question, so I will address it here. I love fisting. I love the feeling of my entire hand slipping inside you and being encased so tightly by your ass muscles. I love rubbing my knuckles back and forth against your prostate. I love the collaborative aspect of fisting, requiring even more communication than other ass play. Believe it or not, I sometimes have (tantric/breath) orgasms while fisting you!
Just because you find the idea of fisting to be a turn on, may have taken 4 or 5 fingers before, or were even fisted a few months ago do not mean you are ready to be fisted by me right now. Fisting is something that you must prepare for on your own, using thicker and thicker toys every 2-3 days over several months until you can easily take a toy 3" in diameter. Once you can take a 3" diameter toy, you are ready for my fist. Sorry, but as much as I love fisting, I can't magically fist someone who hasn't done their own preparation.
May I buy you presents? Where are your wishlists?
Of course you may buy me presents, and you don't even need my shipping address! I have a wishlist at amazon.com that contains limited sex toys, lots of sex related books, and miscellaneous technology to make my life better. My kinky wishlists are through stockroom.com. Here is my wishlist for sex toys, my wishlist for BDSM toys, and yet another wishlist for latex clothing. [A note about the latex clothing wishlist: I don't want all the latex clothing to be black, which is the default on the site. To order different colors, you don't have to call them like the page says; just put the color requests in the "notes" field of the order. Colors I want are: Pearl Purple, Royal Blue, Red, Pearl Pewter, or Black.] If you buy me clothes, you can have a private webcam fashion show for free! The same applies for sex and BDSM toys.
If you want to bring me presents in person when you see me, please only bring sex toys made out of silicone, glass, or metal. My collection is pretty well balanced at the moment, so take a look at the picture of it in the gallery before you get me something. My feet are size 7.5 (8 if only whole sizes are available) and NOT narrow width. Shoes in colors other than black are less likely to get worn than black ones. Gift certificates for massages and/or spa treatments in places local to Allston, MA are certainly welcome. For lingerie, bras must be sized 34 or 36 FF with panties being medium or size 6.
I’m a dominant man; would I still enjoy this?
Asses are a way to access tremendous pleasure that isn't inherently dominant or submissive. Being penetrated only makes you submissive if you see it that way. I certainly don't feel submissive when I get penetrated! If it’s important to you to stay in a dominant mindset, you can interpret my confidence the same way you would the confidence of a talented massage therapist; I’ll just happen to be skillfully massaging your prostate. For this experience, you are not required to be in a “submissive” body position, and I don't have to use the strap-on. All it takes is one finger for you to experience it.
I’m a submissive man; will you dominate me?
I am certainly comfortable in a dominant role, but I am not a domme. I enjoy being, but don't need to be, the Top / person in control / fuck-er instead of the fuck-ee / dominant. And sometimes, depending on our chemistry, that role comes naturally to me. But you should know that when I do go there, that I am the sensual sort of domme, not cruel or physically punishing. In my absolute mastery of asses, I exude a confidence that is often interpreted as dominant. I know I can make your ass feel good and I know exactly how to do it. So it is just fine by me if you feel submissive when I’m plowing you or have you impaled on my fingers, turned into my hand puppet. To sum up, I'm an ass-fucker who does a bit of domination, not a domme who does a bit of ass-fucking.
However, even if I do feel dominant with you, I will not humiliate you for being fucked in the ass or humiliate you via "forced feminization" (which is totally different from the cross-dressing support described on the sessions page).
Will you dominate me verbally?
I’m usually quite focused on fucking you and don’t always get verbally dominant spontaneously, even if the chemistry is there. If you want me to be verbal, I encourage you to get the ball rolling by asking me if you are a good little [submissive label of your choice]. If the chemistry is there, I’ll run with it…if not, I’ll still do a great job fucking your ass. I don’t fake it if it doesn’t come naturally, and don’t have a rehearsed script; I’m allergic to cheese. ;-)
Why don't you call it “training?”
It's just play for me. I'm not training you to do anything. Sorry, but it's a piece of domme-speak that I just don't buy into, at least not in the traditional sense of training you to be a good submissive or to serve me. However, I can be thought of as a coach, helping you learn how to get more pleasure from your ass.
Sure! I love playing with women too, including their asses. Some people might think that anal sex for women can't be pleasurable because we don't have a prostate, but G-spot stimulation through the ass is possible; personally, I prefer G-spot stimulation via my ass instead of my pussy. However, the limitations on off-limits parts of my body (pussy, asshole, nipples, and face) still apply.
Do you offer services for couples?
Yup! I can teach a woman how to use a strap-on and/or play with her partner's ass, including prostate or g-spot massage via the ass, depending on whether that partner is male or another female. I can teach a man how to warm up and fuck his partner’s ass. I can help you try several dildos and provide guidance in shopping for a harness. I enjoy seeing couples interacting and expressing their genuine chemistry, but don't watch in a lecherous way. I can coach you with each other or play with one or both partners' asses. An hour and a half is the minimum length session necessary for couples, but two or more hours are recommended.
You’re amazing.
Thanks, but that’s not a question.
Will you marry me?
No.
Where are you located?
When I am traveling, I am located in an upscale hotel in a nice neighborhood in whatever city I am visiting. When I am home in the Boston area, I'm located in Allston/Brighton, near both the B and C branches of the Green Line. I'm in a discreet building with several apartments and a buzzer to let you in. Since parking is notoriously hard to find in this neighborhood, I have a private designated parking space located a 4 minute walk from my apartment. I have a shower that you are welcome to use, equipped with soap, shampoo, conditioner, and clean towels.
Will you come to me?
No. Don’t ask.
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I hope this information has been helpful to you, and I’m looking forward to getting my hands (and other implements) on your ass. If you have any more questions, don’t hesitate to email me at 
or IM me at BostonStrapOnJo on AIM or Yahoo! IM.
