Stef Woods

Playing hooky

It was a cold and rainy Tuesday in late March. I was lounging on the couch in my Old Navy sweats when my phone vibrated. It was a text from Mr. Exec:

Morning. What are your plans for today?

Me: A whole lotta nothing!

Mr. Exec: That sounds nice. Up for some company?

Me: Sure :)!

Mr. Exec: I might need your help with an article for a newsletter for [an organization that had a similar mission to a nonprofit for which I used to work]. Would that be okay?

Me: Of course!

Mr. Exec arrived at my place a couple of hours later. He has his nickname for a reason so I was surprised that he barely looked at his Blackberry all day. He fully committed to playing hooky with me and being a sloth. I hadn't expected him to be able to decompress from his job the way he did, and it was nice to see.

Even though Mr. Exec hadn't even kissed me at the end of our first date or even come upstairs, it felt like he had been over my place many a time. I poured him a glass of Chardonnay. We relaxed on the couch, watching Sportscenter. He put his arm around me and made sure that my blanket covered my feet. I hadn't thought about what this embryonic thing called "us" would turn into, but we interacted like we were a couple.

That afternoon, ESPN kept replaying Tiger Woods' interview.

Mr. Exec: If you were Elin, would you stay?

Me: Hell no.

Mr. Exec: What about for better or worse?

Me: That would go out the window if my husband put his cock inside one other woman — let alone 12.

Mr. Exec: Would you leave a person if he was an alcoholic?

Me: I was in a relationship with an addict and an alcoholic when I was in my early 20s. I became such an co-dependent enabler that I don't think I would knowingly become involved with an addict again unless he was in recovery.

Mr. Exec: Well, what if he didn't have a problem, but a tragic event like a family member's death sent him into a downward spiral? Wouldn't you want to help him?

Me: Of course.

Mr. Exec: Then, how is an alcohol addiction different from a sex addiction?

Me: I don't see what Tiger did as situational or a post-traumatic stress response. Cheating would involve a betrayal of our marriage vows so I see that as different from a substance problem. But, I get your point that if marriage is forever, that includes the worse.

We talked more about our views on cheating and sex addiction. I might not have agreed with all of Mr. Exec's points, but I respected them. I liked his energy and his wisdom. I hadn't dated anyone with whom I felt such physical and intellectual chemistry since Lawyer Boy.

Mr. Exec suggested that we take a nap, but I decided to crack the metaphorical whip and get the article done before we went to sleep. I felt flattered that he trusted me to help him with it, and we worked well together. I had a thought that if we continued dating, there would be a lot more of this. I smiled to myself in front of the laptop (much like I'm doing now). I had definitely missed being able to professionally connect with someone.

When we finished the article, we began talking about upcoming events in town. That made me think of his friend, Jenna, who I had met last year.

Me: How is she? She was so much fun.

He commented that he hadn't talked to her in a while, noting that he received a lot of flack for bringing her to the event in Georgetown.

Me [surprised since I thought that they were just friends]: Was she there as your date?

Mr. Exec: Well…we were hanging out.

Me: Wait a minute… you were flirting with me and asking me out right in front of her? And, she was there as your date?

Mr. Exec: Yes.

Me: What kind of guy is on a date with one girl and asks another girl out right in front of her?

Mr. Exec: Well, Jenna and I weren't serious. We didn't have that much in common. She's nice, but I didn't see it progressing so I didn't view it as a big deal.

Me [laughing out loud]: Seriously? I actually wondered why I had never heard from her since we had gotten along so well. Now I know why. I would have walked out of the restaurant if you had done that with me.

I rolled my eyes and thought to myself:

What was I getting myself into?

Tea for two

As my date with Mr. Exec approached, I found myself a bit giddy. Mr. Exec was handsome, successful and intriguing, and I was looking forward to spending more time with him. I could tell just how excited I was by the fact that I told my friends about my plans.

JD: Where did you meet him again?

Me: At a charity event last year. He had asked me out back then, but I was still with "Buckeyes" Boy. I'll guess we'll see if our timing is better now.

JD: So, where is he taking you?

Me: Out for tea.

JD: Tea? [Laughing out loud.] He's taking you out for tea? What straight guy invites someone out for tea?

Me: Come on. That's his thing. He mentioned that to me last year. I don't drink coffee anyway so what does it matter?

JD: Is he black?

Me: Yeah. Light-skinned.

JD: British?

Me: No. Enough! It's not a big deal, k?

JD found the whole "tea" meet-up to be suspect, but I chose not to over-analyze our plans for the evening. Mr. Exec and I had also been texting about watching the Georgetown-Marquette game afterward. I liked the idea that the date could be tea and more.

I wanted to look cute without being overdressed. (This was just a casual date, after all.) And, as is often the case in March, it was raining outside. I chose a red sweater, my skinny black Twenty8Twelve jeans and my black Burberry jacket.

When I arrived at Teaism Dupont, Mr. Exec was out front. He gave me a kiss on the cheek to say hello. When we noticed what the other was wearing, we started to laugh out loud. Mr. Exec had a black Burberry jacket and jeans on. We looked like twins!

We went inside, ordered tea and headed upstairs to a table. It didn't take me more than a few seconds to remember what a smart guy he was and how easily our conversation flowed. Mr. Exec and I talked about the usual topics that a couple does on a first date: education; places we've lived; work and family. The more he spoke about how he was raised, the more I smiled. It was clear that Mr. Exec was a total Momma's Boy.

After an hour at Teaism, he said,

Shall we go to a bar to watch the rest of the game?

Me [smiling]: That would be great.

He suggested that we head down to South Dupont and watch the game at a bar with more of a sports vibe. While we were walking, we heard Bell Biv Devoe's "Poison" coming from a bar below Darlington House.

Me: Is it 1990? What's next? Someone will start doing the running man?

Neither of us said anything to each other, but there, in the middle of the sidewalk on Connecticut Avenue, we both broke out into the running man. I switched it up to the slide move that BBD was known for as Mr. Exec worked the Cabbage Patch.

When we finished our dance break, we laughed so hard that I had tears in my eyes. Mr. Exec then commented,

We have to go into that bar now.

We walked inside and realized that was the perfect place to watch the game. We bellied up to the bar to order drinks and some appetizers.

Mr. Exec: So, I have to admit that I haven't looked at your blog.

Me: That's not necessarily a bad thing. (I don't care for a guy to read about the explicit details of my past relationships anymore than I care to read about theirs.)

Mr. Exec: Well, I wanted to go to your Blog Party to show you that I support you, but I didn't fully understand what happened with "Buckeyes" Boy. Are you comfortable talking about it?

Me: Sure. I didn't do anything wrong so I'm fine talking about him.

I condensed my relationship and the aftermath into a seven-minute conversation. I didn't want to belabor the situation or raise concern that I might not be over "Buckeyes" Boy. But, Mr. Exec had several questions about my relationship, and I wanted to answer them honestly.

Me: This is a small town. "Buckeyes" Boy has lied to numerous people in the Twitter community, a recruiter and people in his workplace. It's only a matter of time before he lies himself right out of this city.

Mr. Exec: Definitely. People don't realize how it all comes out eventually. DC is too small for it not to. For instance, Nikki [a friend of his who I had met] was telling me about this guy who kept asking her out last year. He said how much he liked her and that he wanted to take her to dinner. She considered it, but then she told me his name. I was like, 'There's no way you can go out with The Baron. He's a crook.'

Me: The Baron?

Mr. Exec: Yeah, do you know him?

Me: Umm…yeah…we went to law school together.

I figured that was easier than saying,

Oh, you mean the guy who I spent New Year's with?

Yeah. My world is way too small.

Wrapping it up

I recently received the following question on Formspring:

I have had unprotected sex a couple of times, and I know it's a bad idea for the future. How do you bring it up without ruining the mood? Also, who should carry the condoms: the man or the woman? (I don't know how to pick them out since each guy is different.)

To state the obvious, few people enjoy using condoms. But, there is a key difference between wanting to use a condom and needing to use a condom. Unless you and your boyfriend are in a monogamous relationship and have both been tested for HIV and STDs, he should be wearing a condom each and every time you have sex. (I'm sure I'm not telling you anything that you don't know, but it can't hurt to be reminded again.)

Since you have had unprotected sex, have you made an appointment to get tested yet? If not, I recommend doing so in the near future. Most major health insurance companies cover an HIV test as part of your annual physical, and you can be tested for STDs at your annual OB/GYN appointment. If you are attending college, confirm that you can get tested at your school's health center. If your school doesn't offer those services, then check online to find out where the nearest Planned Parenthood or women's center is.

Since you don't care to have unprotected sex in the future, how can you bring up the topic without ruining the mood? Well, that depends on the nature of the relationship:

1. A one-night stand or more casual relationship. You aren't seriously dating anyone and are meeting your girlfriends for drinks. You're open to wherever the evening takes you if you meet a fine guy or receive a text from Mr. Right Now.

Be prepared before you leave the house. Buy a cute condom compact and a box of condoms. Keep the box at your house and before you go out for the evening, place a few condoms in the compact. Throw the compact in your purse along with your keys, phone and lip gloss, and you're ready to go!

Prior to having sex, I imagine that the guy will reach for a condom. If he doesn't say or do anything, put your hands on his face and look into his eyes as you say:

I want you inside me. Do you have a condom?

(If you like to talk dirty, feel free to substitute the first line with any variation of "I want to fuck you.")

If he has a condom, then let him use whatever condom he prefers. If he doesn't have one, then you can reach over and grab a condom out of your purse. It doesn't need to ruin the mood since using a condom is a means to a hopefully enjoyable end! If the mention of the word, "condom," makes the guy less excited (as in, less hard), then take a few minutes to get him just how you want him before he puts on the condom.

Most guys in this day and age should realize that it's dangerous to have unprotected sex. But, there are still those guys who will break out a line to try to convince you otherwise. Be prepared with your responses. For example:

Guy: I'll just put the tip in.
Girl: We both know where that will lead.

Guy: I can't feel anything with a condom.
Girl: I bet you will. I'm very wet.

Guy: I don't want to use a condom.
Girl: We can just mess around without having sex, but wouldn't sex be more fun?

Guy: Aren't you on the pill?
Girl: That's not the point. We don't know each other well enough to go raw.

You can use whatever words you wish to get the point across. Just know your limits and stick to them.

With respect to ruining the mood, I would try to reframe your thoughts on that. Using a condom when you have sex should be viewed as Standard Operating Procedure, not a buzz kill. Unless you and the guy are in a monogamous relationship and have both been tested, then the risks of not using a condom FAR outweigh the 60 seconds it takes to bring it up and put one on. (Please realize how much of an understatement this is and that I could go on and on about how testing positive for HIV or dealing with an unplanned pregnancy could really ruin the mood.) Just view using a condom as a normal part of the routine of having sex.

What condoms should you buy? You could buy a Variety Pack from Durex or Trojan or pick a lubricated, latex condom that you like. Choose latex over lambskin since lambskin does not prevent again STDs.

If you want to cover all your bases, you can also pick up a box of Trojan Magnums for larger men and throw one of those condoms in the compact. Trojan's bestseller is the lubricated, ultra-thin ENZ condom, but the company recently came out with an ultra-ribbed Ecstasy condom. (The Ecstasy claims to let you feel all of the pleasure without feeling the condom. Has anyone tried one of these condoms? What was your experience? Please comment – anonymously if need be – and let us know.)

2. If you're in a relationship, then the topic of condoms becomes part of a larger discussion of past sexual history and birth control. I think it's easier to have those discussions out of the bedroom so that there's less pressure. But, if you prefer to have that conversation in the bedroom, that's fine, too. (It's more important that you talk about it than where you talk about it.)

If you care about this person, then it's worth communicating about the following things:

Are you using condoms for birth control and STD/HIV prevention or just the latter?

What condom does he like best? Will he be providing them or do you need to stock up, too?

Will you be using condoms in the early stage of your relationship with the intent to get tested later on?

Are you both monogamous?

Can you orgasm with condoms or will you need additional clitoral stimulation?

You might address all these issues in one fell swoop or discuss these matters over time. If you are in a relationship with someone, then it's appropriate and necessary to broach all of these topics. Just remember that communication and honesty are keys to a healthy relationship in all senses of the word!

Have fun and be safe! xoxo

How have you broached condom use with a partner? What's your brand of choice and why?

Teddy Ruxpin

Last Friday morning, I was trying to motivate out of my warm bed and into the shower when the telephone rang. I looked at the Caller ID and saw that it was Philly Matt. Given the timing of his call, I realized that he had just read my latest post about us.

When we spoke earlier in the week, Matt had told me about Tammy, a girl he recently met. His voice was giddy when he talked about her in a way that I hadn't heard since he and I had dated. I was excited for him on the phone, but when we hung up, I felt melancholy. What would happen to our friendship? How would our relationship change with a girlfriend in the picture?

I thought about texting or calling Philly Matt that evening, but instead, I just wrote a post about it. In retrospect, that was a passive-aggressive move on my part since I know that Philly Matt reads my blog regularly. But, I figured that the conversation would come soon enough, and it did.

Philly Matt [hearing the groggy tone in my voice]: Did I wake you? I'm sorry. You can go back to sleep and just call me later.

Me: No, I'm good. Just waiting for my migraine meds to kick in. What's up?

Philly Matt: So…I read your post.

Me [with a bit of nervousness in my voice]: Yeah, I figured.

Philly Matt: I read everyone's comments, too. I thought about writing one of my own as Philly Matt, but I decided that I should just call you.

Me: Okay. You know you can write one anytime you want, though, right? Even if I disagree with it, I'll still approve it.

Philly Matt: I know that, but it just made more sense to talk to you directly.

Me [exhaling]: K.

Philly Matt: I want you in my life until the day I take my last breath. You are a very important person to me and anyone I date will need to know that and be okay with that. If you call me in the middle of the night and need me, she's going to need to understand that I have to go. Staying friends with you is not negotiable.

I paused for a few seconds after he said that because I had tears in my eyes. (And, yes, being the sap that I am, I have tears in my eyes again as I'm writing about this.)

Me: Thanks. I figured that's what you would say, but it means a lot to me to hear that. I couldn't imagine my life without you.

Philly Matt: And you won't have to.

We talked for a while about how our relationship doesn't make sense to most people.

Philly Matt: Maybe they haven't found a way to make it work. Or didn't break up amicably.

Me: Well, it's not like we were friends right after we broke up so I understand. But, I feel closer to you now than I did when we were a couple. We've been through a lot over the past few years.

Philly Matt: Exactly. I know that no matter what, you're there for me. And, you know that the same is true with me. Anyone we date will need to understand that, too.

Me: Thanks. That makes me feel better. I still feel bad that I even considered not having you come on the ski trip with "Buckeyes" Boy.

Philly Matt: Well, you guys were in a serious relationship. You couldn't make him uncomfortable. I knew that you and I would stay friends no matter what, but I just felt bad that I wouldn't be able to go on the ski trip or see everyone else [in our group] anymore.

Me: Yeah, I know. I'm glad that didn't happen, and I've learned my lesson for next time. I don't want to lose you or isolate you from the group. The Crew wants you around, too. And I also realize that I'm acting pretty selfish to be whining about a girl that you haven't even really started dating when I've called you about several guys over the years and you've always rolled with it. I guess I just worried that I would lose you if you got serious with a girl…that she wouldn't understand.

Philly Matt: That's never going to happen with us. She's going to know about you. I feel closer to you now than I did even a few months ago after having met your Dad and Rhea [my Dad's girlfriend at my birthday party in April]. . . .And, you realize that I've barely spent any time with Tammy one-on-one. I don't even know if we'll start dating!

Me: Yeah, I know. It just caught me off guard to hear how you talked about her. Tammy's your first crush since me, and I guess I got a little jealous and a little confused, even though I'm happy for you. [Pause.] I'm okay with us never hooking up again, but losing your friendship would be too tough for me. You know me better than any guy I've ever known. [Pause.] But, I will miss snuggling with you. You are very snuggly.

Philly Matt: I'm a regular Teddy Ruxpin! [We start laughing hysterically.]

Me: You pulled out Teddy Ruxpin?!? Hahaha!

Our conversation shifted gears to work, friends, his kids and my latest guy adventures. When I hung up the phone 30 minutes later, I had a huge smile on my face and wiped a few more tears of joy from my eyes.

I wish I knew the secret to how Philly Matt and I have managed to make our friendship work. (Trust me, I would bottle that formula if I could.)

As I texted Philly Matt this weekend,

I love you, Teddy Ruxpin!

And, I do. With all my heart.

Did you try it out and then the friendship fizzled over time or when a new significant other came into the picture? Do you regret not maintaining a friendship with any of your exes?

In like a lion

Last October, I attended a charity event on the Hill. When I walked into the venue, I immediately noticed Mr. Exec, a very successful business consultant. He's 6'1" with an athletic build and light black complexion. His most striking feature: his blue-green eyes that sparkled like the water off of Seven Mile Beach. A close second: his impeccably tailored designer suit.

At the event, Mr. Exec took me under his wing. If I wanted a drink, he made sure that I had it in less than a minute. If there were A-listers in the vicinity, he introduced us and told them about my blog. If the photographer was nearby, he made sure that she took several pictures of me.

Mr. Exec: Are you going to the after-party?

Me: No, unfortunately, I have to go home.

Mr. Exec: Would you like to go out for tea sometime?

Me: Sure! That would be great!

Mr. Exec sent me an e-mail after the event. I indicated that I was open for grabbing tea, but he never threw out a specific day or time. I didn't pursue it since I was busy with my thesis and was living with my then-boyfriend, "Buckeyes" Boy.

A month later, the charity held another event in Georgetown. Mr. Exec and I texted each other beforehand to confirm that we both would be attending. Mr. Exec showed up at the event with his friend, Jenna, yet he still paid a lot of attention to me. He reiterated his offer to have tea together and also mentioned grabbing a meal at National Harbor.

Mr. Exec, Jenna and I spent much of the event talking to each other. For some of the conversation, Mr. Exec had his arm around my waist. But then, he moved it to my ass. That caught me off guard. I had always felt a friendly vibe between us, but my judgment might have been clouded by the fact that I was in a serious relationship. I waited for the next appropriate moment to mention that I had a boyfriend, hoping that would eliminate any further ass grabbing.

After that event, Mr. Exec texted me about getting together on Sunday. We were trying to coordinate plans, when he made a comment about wanting to give me kisses.

Me: Hugs – yes. Kisses – no.

Mr. Exec: Why not hugs and kisses?

Me: Because I'm living with my boyfriend and that wouldn't be right.

Mr. Exec: Oh, I didn't know that.

Me: Yeah, but I would love to go out for tea with you as friends :).

Mr. Exec suddenly became much less available for tea, but I couldn't blame him. I didn't hear from him again for over a month, when he texted me to wish me a Happy New Year.

We then began to text more regularly, but it was tough to find a time to get together. (I was in thesis mode in January, and DC was covered with snow for most of February.) When Mr. Exec heard about my Blog Party in March, he told me that he would love to come to support me. That made me smile.

In the same text conversation, he also asked me out for tea on the Friday after the party. I said yes without hesitation. As the week progressed, I got more and more excited. I wasn't able to be more than Mr. Exec's friend five months ago, but maybe our timing was better now?

When Mr. Exec walked into Black Finn for my party, a huge smile came over my face. I was able to look at him now and feel an attraction. We talked for a few minutes before I went to mingle.

When it came time for me to make a speech, I talked about why I started blogging and how my relationship with "Buckeyes" Boy ended. As I told the group, I was going to pursue my goal to adopt a child, but I also had a lot more dating — and more blogging — to do!

When I saw Mr. Exec later on in the night, I jokingly asked him:

So are we still on for Friday night?

Mr. Exec: Of course we are. Why wouldn't we be?

Me: I didn't know if I scared you off with anything I said.

Mr. Exec [smiling]: Not all all.

Me [smiling]: Good.

I was ready to date again and was looking forward to getting to know Mr. Exec better. March was definitely roaring in like a lion, and that was a good thing!

Somewhat Delightful

Are you looking for a toy for G-Spot stimulation that's a better quality product than the Rabbit? 

The women at Lotus Blooms recommend Lelo's Iris and Fun Factory's Delight because of the caliber of their products. I chose Fun Factory's Delight since that toy also provides clitoral stimulation. The Delight is made from 100% Medical Grade silicone so it's good for your skin and your body. (Phthalate-free is the only way to be!)

The Delight comes in a carrying case with an external charger. There are no batteries required, which is a huge plus! The case is so discreet that you'd expect to find a pair of sunglasses inside.

The Delight is available in black and white or pink. I chose pink since it seemed feminine. I also felt like the shape in black and white reminded me of a small whale, which just isn't sexy to me.

The toy is S-shaped so that you can easily insert it so it hits the G-Spot just so. It was made with ergonomics in mind so can grip the toy with your index finger and thumb. You then move your thumb on the top of the toy to operate the controls.

There is a positive sign and a negative sign where your thumb rests, and the control panel illuminates when touched. You may need to touch the positive sign up to four times in a row before the toy turns on. (For those of us who expect instant gratification, it helps to know that in advance to avoid getting frustrated. When I first used the toy and couldn't figure out how to turn it on, I was cursing at it for a few seconds. That's never fun!)

The Delight has eight (8) speeds. Press the positive sign to increase the intensity and the negative sign to decrease. Once the toy has been on for a few minutes, you can then continue to press the positive sign to change from constant vibrations to varying speeds.

It's most comfortable to use the toy if you are lying on your back or on sitting on a couch with your head and back upright and your legs out in front of you. Feel free to experiment on your own, but it was awkward to use the toy face down.

This toy features an added piece of silicone for clitoral stimulation. However, one size does not fit all! I had a hard time positioning the toy on my G-Spot and my clit simultaneously. I wondered if that was just how my body is shaped, but a friend who owns the Delight had the exact same problem. The product can give amazing G-Spot orgasms and is sleeker than most adult toys. But, I wouldn't pitch the Delight as dual-purpose since the clitoral stimulation is minimal at best.

The toy is very quiet and doesn't look like your typical, dildo-shaped vibrator. (That's a plus for those of you who don't want to wake up roommates, kids, parents or significant others.) The Delight is also aesthetically-pleasing and wouldn't be intimidating to pull into the bedroom for use with your partner.

There is one big negative to the product, though, and that's the price! The Delight retails for a pricey $109.99.

The Delight was the first toy that I paid more than three figures for so my expectations were higher. I wanted more bang since I shelled out so many bucks. And, I have to say that the Delight came up short. Fun Factory's Delight is a great toy for finding your G-Spot, but the toy has gathered a lot more dust than…

Have you tried the Delight or a similar high-end sex toy? What was your experience?

Are You Ready To Lose It?

I received the following question on Formspring last week:

Hey City Girl!! I wanted your advice on losing one's virginity. How do you know when the time is right? I have an amazing bf but am still worried about my first time and don't want it to be a bad experience. Any advice?

Here are my thoughts:

The short answer to your question is that I can't tell you whether to lose your virginity or not. That's a decision for you and your boyfriend to make. (I've said the same thing when readers ask me about trying anal, a threesome or having sex shortly after ending a serious relationship.)

With that disclaimer, there are definitely factors to consider as you make your decision. Here are a few that come to my mind:

1. Why have you waited up until this point? If your interest in losing your virginity is based on pressure that you feel from your boyfriend or friends who have already had sex, then you might want to wait to be sure that the decision is yours and yours alone. If you've waited until your relationship has reached a certain milestone (three months of dating or an engagement ring, for example), then have you reached that milestone? If so, do you still feel the same?

2. What expectations do you have about your first time? I loved my high school boyfriend, Boston Christian, with all my heart. I've never regretted losing my virginity to him for a second, but the act was also incredibly painful. Sharing that experience together was wonderful because we loved each other as much as two teenagers can, but the sex wasn't.

Are you close enough as a couple that you could make it past a bad experience? Would you be okay if it doesn't turn out perfectly? What are your expectations of losing your virginity? Are you both on the same page in terms of how you feel about each other so that adding sex to the mix won't complicate things?

3. Have you discussed all the possible ramifications of pregnancy, STDs and AIDS with your boyfriend? If you don't feel comfortable talking about these topics with him, then I would question whether you are ready to have sex. Are these issues easy to bring up? No. But, they are necessary. Are you both going to be in a sexually-monogamous relationship? Will he be wearing a condom? Are you on birth control? Has he been with anyone before you? If so, do you want him to get tested first?

I addressed some similar issues in last month's post about: How soon is too soon to have sex with a new guy? Determining relationship expectations and discussing birth control and STD/HIV testing need to happen whether it's your first sexual partner or your 50th.

Please take this post as friendly advice, rather than encouragement or discouragement. If you read through this and decide that you're ready, then you are! But, if the post raises more questions for you than answers, then you might prefer to wait. You can always decide at a later point that you're ready. There's no right or wrong so just follow your heart, use your head and be safe! xoxo

Readers: What would you recommend? How was your first time?

My thoughts on Boobquake

In 1953, a young woman evaluated her options for going to college. She was an Honor Roll student and wanted to apply for a scholarship to the state university. Her guidance counselor told her:

You shouldn't apply since you're just going to get married after high school anyway.

She refused to be undeterred, working at the local YMCA to save money for night school. After college, she secured a job, managing an advertising agency in Manhattan. Her managerial style was no-nonsense, but effective. Her co-workers called her, "Dragon Lady," and rather than run from that title, she embraced it.

In the late 1960s, she was one of the charter members of a local NOW (National Organization for Women) chapter. And, she didn't follow the path that her guidance counselor predicted. She married at age 34 and had her only child, me, two years later.

My Mom raised me to believe that I could do anything and be anything. She hoped that I could be respected for being a strong and educated person. She taught me about equal rights and feminism when I was in elementary school.

The world in many senses was my oyster. Nonetheless, as far as women's rights had come, I learned at an early age that being a girl wasn't the same as being a boy. (And, no, I'm not talking about biology or anatomy here.) Two examples:

In fourth grade, I was the Teacher's Pet. (If you knew me then or know me now, that shouldn't be hard to picture.) When I finished my work, I would grade everyone else's papers in class. I knew that I had the elementary school equivalent of straight As, and that one boy in class had one B and the rest As.

However, when report cards were issued, he had all As, and I received one B. My parents asked about that in their conference with my teacher and were informed:

Boys need encouragement, and girls shouldn't have things handed to them too easily.

In high school, I went out one night with a guy, Golf Boy. He proceeded to tell the entire school what we did and even lied about having a videotape of our evening. I tried my best to ignore him after that. But in History, he came over to my desk, got on the floor in front of me, and put his hands up my poof skirt to touch my underwear.

Several other people in the class laughed, and I yelled a few expletives at him. The female teacher saw what had happened, and made me put 75 cents in the curse jar for saying three bad words. She didn't punish him at all.

When it came time to select a college, I chose a woman's college. My school allowed all of us to shine in one way or another, and I grew without having to worry about sexism holding me back.

I took several classes on women and the law. Sexual harassment in the workplace was brought up in the curriculum on more than one occasion. We were taught that harassment wasn't to be tolerated in any circumstance.

Those lessons and the relevant case law were in the back of my head when I began my first job out of college. As a legal assistant, I worked long hours and would often go to a club afterward.

Since sexual harassment was wrong, I thought that meant that I could dress however I wanted to at work. If my dress was a little short or my blouse was a little too tight around my chest, then who had the right to care? I should be judged solely on my work performance. And, besides, I really didn't want to go home at 11pm to change.

I started to notice something, though. As smart as I was and as strong as my work product was, the partners in the law firm felt like they were justified in making inappropriate comments about my dress or me.

"Your guy couldn't hold onto his balls this weekend," one attorney said after my then-boyfriend fumbled in Sunday's NFL game.

"You're a sexual harassment law suit waiting to happen," another partner told me in my first job after law school.

"The things I could do to you," my boss informed me.

I realized that there was a correlation between how I dressed and how seriously I was taken professionally. I'm not saying that was right. (In fact, I think the comments that were made to me were incredibly inappropriate.) But, the adage, "boys will be boys," has been around for such a long time for a reason.

With the first two examples, I was offended, yet I never filed a complaint. By the third, I was confident enough in my work abilities to call my superior out on his behavior directly:

"You wish you could handle this, but we both know you can't. Can we get back to the case now?" I told him with a firm attitude and a big smile.

He never made a comment about my appearance again.

I also reevaluated what I could do to be taken more seriously in the workplace. I left my mini-skirts and tight sweaters at home and invested in a lot of Ann Taylor and Tahari suits. I noticed how people responded to me differently. My opinion and my accomplishments were more respected. I liked that.

Why am I writing about all of this on a relationship and sex blog? I love my sexuality and my curves. But, I also love being taken seriously as an attorney. If we lived in a society that didn't view women as sex objects, then I could be both a lawyer and a sex blogger. But, that's not the reality. Double standards may not be as overt as they once were, but that doesn't mean they don't exist.

I, thus, didn't feel comfortable participating in Boobquake today. (For those of you who are unaware about what Boobquake is, read here.)

I'm thankful that women in the United States have countless freedoms that women in so many other countries do not. I admire the idealism and social media savvy of the college senior, Jennifer McCreight, who came up with the idea to for women to wear low-cut tops. The goal of Boobquake: to test (mock?) Iranian Prayer Leader Sedighi's theory that dressing immodestly causes earthquakes. I vehemently disagree with religions, cultures and regimes that try to suppress women educationally, economically, politically and personally. But, I've learned that I can be a better advocate for those women and myself, if I keep my revealing attire out of the workplace.

I support those of you women who wore low-cut tops today in protest of Sedighi's misogynistic and misinformed statements. But, I hope that you'll also support me. I'm the woman in the black Ann Taylor pants suit with sensible heels to your left. Yeah, that's me. I'm Dragon Lady's daughter and proud of it.

Did you celebrate Boobquake? Was it just a college joke, in spite of the media coverage and massive on line support? With an estimated 200,000 participants, how can this event turn into something more to advance women's issues?

How soon is too soon to have sex with a new guy?

When I was in NYC recently, I had lunch with an old friend. In less than a month, her long-term boyfriend had broken up with her, and she met a great new guy. We started discussing her current relationship, and she asked me:

How soon is too soon to have sex with the new guy?

I'll gladly tackle the question with the disclaimer that there's no right or wrong answer here. I know couples that have had sex the first night they met and are happily married years later. There are also women out there who have waited to have sex with a guy, thinking that he was "The One," only to have sex with him and find out that he wasn't.

With that in mind, what factors should you consider before jumping in bed with a guy?

1. What are you looking for?

Sex: More than a few young women are raised to feel like it's wrong to view sex or want to hook up like men do. There are many double standards when it comes to relationships and sex, but that doesn't mean that those standards are right. What's wrong with using a man for sex like a man might do to you, provided that you can emotionally handle a connection that's purely physical? If what a girl wants is a one-night stand or casual sex, then there's no need to wait. Practice safe sex every time, find a place that is comfortable for you both, and make sure that you know the guy well enough to know that if you set boundaries, they will be respected. Beyond that, have fun!

Love: If you are looking for a relationship with a solid, emotionally-based connection, then I recommend waiting before adding sex into the equation. Give yourself time to make sure that you both are on the same page in terms of compatibility and what you are looking for out of the relationship. Focus on activities outside the bedroom to really get to know each other. Enjoy kissing and other non-sexual forms of affection and romantic expression. Make sure that you both are equally as invested in the relationship and that you are spending regular amounts of time together.

If you are always waiting for him to call and don't see each other with much frequency, then you might not be on the same page. If you feel anxious about when you will hear from a new guy or how to define your relationship before you have sex, that feeling will only magnify after you have sex. You can't expect that sex will change a guy's behavior so why not wait to see if you're both looking for a serious relationship before you jump into bed with him?

Discuss birth control, condoms, STD-testing and whether or not you both are in a monogamous relationship before you have sex. If you are waiting to have sex until you're in a long-term relationship, but you don't feel comfortable discussing any of those topics with your man, then you aren't on the same page. (I'm not saying that these topics are fun or easy to bring up, but they are necessary if you're in a monogamous relationship.)

Something between Sex and Love: If you aren't sure of what you're looking for or whether a new guy has long-term potential, then wait until you know or your relationship has been defined. Once you have sex, you can't go back to the beginning stage of the relationship and get to know the guy without sex being part of your normal routine. Remember that there's no harm in waiting.

2. How long should you wait?

I've noticed that I have more clarity about and peace regarding a relationship when I wait to have sex with a guy. I look back at several relationships and was glad to realize before I had sex with a guy that we weren't compatible. Likewise, I could tell which guys truly cared about me because they were interested in more than just sex.

I can't tell you if four dates or a month or Steve Harvey's 90-day probationary period is right for you. What can I recommend then? Take your time, trust your intuition, and do only what makes you feel comfortable. Make sure that you know  If you have concerns that you're having sex too soon in a relationship, then you probably are.

3. How can you tell if you're over your ex?

For my friend, this is integral to the issue of when she should have sex with the new guy. She was in a serious relationship, and her heart was broken. Understandably, she might need time to process that before having sex with the new guy.

When you bounce from one serious relationship to the next, you don't always look at the new partner as purely for sex. But, if you haven't healed from your previous relationship, the new partner ends up being a transitional guy by default.

How often do you think about your ex? Do you find yourself looking at old photos, cards, e-mails or his profiles online with any regularity? Are you still crying or angry about the relationship? If you knew that he would be at a certain place on a given night, would you feel the need to go there to confront him or would you avoid the place altogether because seeing him would be too painful? Are you waiting for him to call, text, IM or e-mail you just because? Are you preoccupied about that one small thing of yours that is still over his place?

An attachment to your ex or a lack thereof might depend on who initiated the breakup, why you broke up, and/or how difficult the latter part of your relationship was. I can't tell you if you're over someone or not, but if you aren't truly sure, then it might make sense to wait to move forward with your new relationship. You owe it to yourself and your new partner to make sure that you're approaching things honestly and openly. Otherwise, Mr. New Guy automatically becomes Mr. Rebound. If that's what you want, then fine. But, if you don't feel certain or you think that the new guy could become something serious, then err on the side of caution and just keep waiting.

Do you have any rules when it comes to having sex with a new partner? How long do you recommend waiting? How could you tell that you were over your ex?

Around the rim

A reader sent me an email on Twitter last month, asking me about rimming.

(For those of you who don't know what rimming is, it involves oral-anal play. Rimming occurs when one person licks, tongues or eats out the other person's asshole. It's also called a rim job, analingus, or tossing salad. The act can be used as foreplay before sex or by itself. There is a misperception that oral-anal play is just for gay men. That's just not true. Rimming is anyone who enjoys anal play irrespective of sexual orientation.)

Here are my two (or 200) cents about rimming:

1. Does your partner want you to lick his or her ass? I don't think that's a given since I know quite a few friends of mine — men and women — don't enjoy anal play at all. Treat rimming much like anal sex and evaluate on a partner-by-partner basis. The majority of my ex-boyfriends have (thankfully) loved anal sex as much as I do, but only one of them wanted me to give him a rim job. There's not necessarily a correlation between whether a guy wants to have anal sex with a woman and whether a guy wants to be on the receiving end of oral-anal play.

2. So…how do you find out if your significant other is interested in rimming? Communication! I never recommend going into any type of anal play blindly since not everyone enjoys that. Pick a time to broach the subject when there is no expectation of sex. Openly talk about likes, dislikes and concerns.

a. How do you or does he/she feel about fingering the anus? If you are or your partner is open to that, how much of a finger feels pleasurable? Sometimes a little goes a long way. Does saliva provide enough lubrication or do you need to use lube for finger-anal play?

b. How about licking? How much tongue is too much? Does it feel comfortable to have some or all of the tongue inside the anus or is just the outside better? (Some of this is trial and error when you are in the moment, but it helps to talk about the act in advance.)

c. Is your partner open to using anal toys? Is there an interest in having a finger lead to a tongue and then lead to a bead or butt play? What are the limits?

d. If you are a man trying to gauge if your woman is interested in having anal sex, it's helpful to talk about what she does or doesn't feel comfortable with. Does she view fingers and a rim job as part of the process to become more acclimated to anal play or does she view those acts as unrelated from anal sex?

e. Are there health concerns here? Make sure that your partner has gone to the bathroom and fully cleaned out his or her system before you head in that direction. (That seems like Rim Job or Anal 101 to me.)

But, there's another, far more serious layer here. There is a risk of hepatitis from rimming. Are you and our partner exclusive? Do you want to get tested for hepatitis, other STDs and parasites before you explore the fine art of salad tossing? Will you be using a condom before you engage in rimming?

Since it's worth noting, yes, you can just let your fingers do the walking or tongue do the talking when you are engaging in hand or oral play. (I actually didn't know how much I enjoyed rimming until a one-night stand with Dominican Boy .) If you care about the person you are with, though, I think that communicating in advance strengthens both your emotional connection with your significant other and the pleasure during the act itself.

3. Now, what if you like to receive a rim job, but don't want to give one to your partner? (That was the second question that my friend on Twitter asked of me.) A few clichés come to mind:

Tit for tat;
What's good for the goose is good for the gander;
Giving is better than receiving; and
You gotta suck it up.

I realize that none of those are particularly eloquent, but I think you get my point. I believe in reciprocity in the bedroom. It doesn't need to be 50-50, but if you want to receive something in the bedroom, it's only fair that you also give.

Think about what doesn't appeal to you about the act and try to remedy the situation. Maybe you first try licking your partner's ass in the shower after you've made sure the area is clean? Or, you could start with a finger before you move on to the tongue? You also don't need to stick your whole tongue inside of your significant other's anus. You can start with just the tip and ease both of you into the act. For those who like anal play, using the tongue on the outside of the anus — back and forth like a paintbrush or in a clockwise motion — can be extremely pleasurable.

You might also want to see if your partner would be open to using a toy in lieu of or before your tongue. Would you feel more relaxed doing it if you've already gotten off or had a glass of wine first? Or, can you please yourself with one hand or a small toy while licking your partner's ass?

Once you do bring your mouth down to the anus, don't do so begrudgingly. If you focus on the negative, it will be less enjoyable for both you and your significant other. Try a few mind over matter tricks. Remind yourself that you enjoy pleasing your partner. Feel sexy because you are doing something that turns him or her on. You might also feel differently if you try to give someone you love a rim job versus engaging in oral-anal play with someone with whom you are in a more casual relationship.

You might enjoy rimming. You might not. But, keep communicating with your partner and experimenting in whatever ways makes you both feel comfortable!

PS Part II to this post about what to do when you are engaging in oral-anal play coming soon.