Lately, I’ve been receiving a lot of emails about things like medical conditions and relationship struggles. I am not a doctor, a therapist, or a “sexpert,” though I could probably use the services of all three. But I will do something rare in this month’s “In the Sack” and attempt to address your inquiries with a bit of seriousness. Don’t worry: this is just a phase. At least that’s what my parents keep saying. (All letters and identities have been edited.)
Help! I need advice. I’m dating this amazingly sexy woman. She is off the charts. She’s got this collection of toys, many of which would likely be illegal in most states, that make her bedroom look like a freakin’ sex store. Not surprisingly, she’s absolutely amazing in bed, to the point that I’m reading books just to keep up with her. I’m holding my own, but only barely. So what’s my problem? She is more than interested in pursuing a fling with an incredibly hot friend of hers. Let’s call her Janie Meally. So here’s my question: how do I hook this up?
Struggling Stallion
Dear Struggling Stallion,
Honestly, I’d let the woman take the lead on this one. Otherwise, you might risk coming across as some lecherous boyfriend trying to bed your lover’s pals. Besides, women have this uncanny ability to flirt each other’s pants off when necessary and then completely erase the experience from their minds if it becomes awkward. More importantly, you need to make sure everyone is on the same page. There’s nothing worse than a fun threesome that becomes an uncomfortable twosome that becomes a lonely onesome.
First, I enjoy your columns, except a few that have been really gross. Here’s something I’ve been meaning to write you for months, ever since your column lamenting the lack of women with a 34B chest size. I think 34B is a very nice size. It’s my wife’s size. The only reason I know it is that she has sent me at least once or twice — probably soon after one of her two hip replacements and two knee replacements, when she was having a much harder time than usual getting around — to buy bras for her. She specified the store, the brand, and the model, as well as the size. I think there aren’t many situations more embarrassing than to be the only man shopping in a lingerie or “intimate apparel” department. You have the feeling that every woman there must think you’re some kind of pervert.
Big Boob
Dear Big Boob,
You know what’s gross? The fact that you only discovered your wife’s bra size when the woman was so incapacitated that she couldn’t walk or leave the house in order to buy her own undergarments. What is wrong with you? She probably knows your shirt size down to the millimeter and the number of blades you like in a razor. You, on the other hand, find it “embarrassing” to shop for bras. That poor woman should drag her wobbly self out of bed and leave your immature ass in the dust.
I am in love with your column! [Perhaps I should] thank God you do not write often enough for me to develop a meaningful infatuation with your thoughts, but regardless of frequency, your words have provided me with the diaphanous hope that a sexy and witty lesbian population exists somewhere within 50 miles of 02115. Although I’ve long occupied a doubtful position on the overall attractiveness [scale] of the Boston lesbian community, and have only become more committed to my shallow convictions with passing experience, your words have offered me comfort in suspecting that there is a whole other vibrant dyke scene out there that I have not come across, one full of clever and humorous lesbians like you. (Please spare me the disillusion if you actually believe otherwise. At the age of 24, I am too young to stop hoping.)
Little Babe
Dear Little Babe,
My poor child. You have been misled. Perhaps my sarcasm fell flat or you caught me on an off week. But I will refrain from bursting your optimistic bubble. With all the flack I receive from the lesbian community, it’s nice to know that one young soul remains unscathed by my jaded rants. Dare I say you might even be inspired by them? If I may impart one bit of advice without tarnishing your image of Boston’s lesbian scene, it would be similar to that of my journalistic forefather, Horace: “Go West, baby dyke.”
I am 48 and have no kids. I would not say this was by choice. It just happened that way, as I was busy with a career and all sorts of other things that the priority just seemed to be put aside. Now I feel very different than in my 30s. One thing is that I can no longer have children of my own — whereas in my 30s I remember thinking I always had that choice. Most of my friends are now married with kids, whereas in my 30s, this was not the case. Now I feel differently. Maybe it is when you suddenly see your parents age or when you see your best friend’s love for her children or suddenly all your friends around you are getting married and pregnant. It is lonelier as you get older, as most people’s lives revolve around “family.” I believe we as a human race are maternal. Some more than others, but that instinct is there. Screaming, drooling kids may not be for many, but I tell you, I saw my sister go through it with three kids and I have to say I miss that part of a family.
Fruitless After 40
Dear Fruitless After 40,
Every time I leave my sister’s compound and her screaming brood, I get a little pang of envy as I walk into my empty, silent apartment. No doubt, as I get older I am becoming part of a minority as an unwed, childless woman. Add the gay thing and I’m soon to be extinct. Aside from my biological family, I’ve worked to create a sort of surrogate family of other unwed friends, friends who don’t plan to have children, and married friends who would never treat me differently because I’m the odd number on the dinner reservation. Keep in mind that your more “traditional” friends probably envy your freedom and detachment. But that’s often little consolation when the plane you’ve been jetsetting in comes to a halt on the runway and there’s no one at the airport to help you with your bags. I get it.
Jeannie Greeley is a freelance writer who collects her mail at jeannieg@comcast.net.
