The Single Woman Hiding Her Group-Sex Proclivities From Her Dates

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Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Single Woman Hiding Her Group-Sex Proclivities From Her Dates: Female, 29, West Village, operations manager, straight, single.

DAY ONE

8 a.m. Off to shower. I shaved last Thursday before I attended a fun foursome that my Cute Older Friend organized. I've decided I want to keep it neatly trimmed. I contemplate if guys like this. Seems like the sex is always dirtier if there is hair. Plus, I'm logging in 80 hours a week at work now, so I'm particularly lazy. 

11 a.m. I have a long conversation with my BFF about this new phenomena I've been experiencing the last six months: men who have sex and suck on your toes at the same time and the direct correlation of how incredible they are in bed. Men never did this to me before 2012, so I conclude that Men's Health probably wrote an article about it earlier this year, and men have taken note.

1 p.m. Confirming plans with Jewish Finance Guy, who I used to hook up with over a year ago. He randomly texted me before Sandy saying he missed eating me out. I tell him I called over Sexy Texan (my go-to booty call) to keep me company during Sandy. I expect him to say, "That's hot," as he has in the past, but instead, this jealous flare of disgust appears, which confuses me as we are not dating, nor would we ever, and I'm pretty sure that he's the only guy whose face I've ever hate-sat on. Nonetheless, he presses on that I come over.

1:15 p.m. JFG cancels me for Monday Night Football with the boys. 

1:23 p.m. JFG asks if we can play it by ear for later tonight. By now, I am completely apathetic.

1:30 p.m. Random text message from Sexy Fireman, who I hooked up with twice in 2009. Simply says, “Hi.” I think about that one threesome we had with his best friend, where he couldn’t get it up and simply watched me get it on with his friend. I ignore SF’s text.

3:30 p.m. Meet COF for coffee. COF loves watching me play with men. I share my trimming-versus-shaving theory with COF, who disagrees and wants to see shaved, which makes me even less enthusiastic about the next time we play. He keeps asking when we will play again, and while I know it will be a lot of fun, I'm pretty passive on the offer.

7:55 p.m. Finally home. I masturbate to porn of a woman having sex with a couple while giving head.

9 p.m. Text from Ex-Boyfriend's Best Friend (who's in a relationship) telling me he is picturing me wearing heels while he goes down on me. I respond by asking how his girlfriend is. No response back.

1 a.m. Another text from SF. "Hey. What's up?" I finally respond, "Not much. About to go to bed." "Can I come over?" "No." "Why not?" "I'm exhausted." " … But I want to go down on you." I don't respond, as by this point, I have passed out.

DAY TWO

7 a.m. I take my time getting ready, as I have a date with Strawberry Blond after work that I have been looking forward to since last week, and I've yet to tell him about my group-sex kink, more or less because I don't think he has much experience in that lifestyle and I don't want to scare him away or be judged by him.

9 a.m. I always think about the hot sex I had with Sexy Mediterranean Man that works in the building I pass every day to get to work. Once he rummaged through my toy drawer, pulled out one of my vibrators, and began using it on my butt. He had no idea about my kinks or fetishes at the time, so this initiative was intoxicating. Maybe SB will be like this, too?

11:58 a.m. Reblogged a few sexy, smutty photos on my secret photo blog that lets me express what I find attractive and sexy. My audience is no one in particular, though a few of my most fond and trusted fuck buddies know the domain address to this secret world of mine.

3:13 p.m. SB sends me a text to confirm our date tonight. Instantly get a bit anxious. Feels good. I realize it's been about seven months since I last felt this particular way.

3:14 p.m. Thinking about SMM, upon realizing that I never got butterflies with him a month ago. I think it's because we had sex so quickly and that we did so many filthy things that I've grown apathetic to him because there is zero challenge. Also, I'm almost sure he lied to me (and my friends) about being single so he could sleep with me. I'd be more annoyed if I wasn't always instantly turned on by our rendezvous.

7 p.m. On my way to my date. Funny how New York looks so different when you have a promising date. I get butterflies on my short walk to the meeting place, which makes me incredibly wet as a result. Interesting.

9:30 p.m. Excellent date; dinner at an Italian restaurant by Rockefeller Center. Very dark and sexy place, quite upscale, filled with lots of suits. No kiss, but we did have a good hug as we said good-bye. I really like SB. There will be a second date, but we never confirmed the day. SB mentioned he typically only has sex in relationships, and the last time he did "go past kissing" was in his last relationship several months ago. Makes me wonder if there is an inner kinky guy in there begging to come out or if he just has a low sex drive. I'm insatiable.

10 p.m.  Stumble to my fuck buddy Sexy Texan's place for some sexy time because I'm a bit drunk from the date with SB and frustrated. ST laughs at my predicament, promptly undresses me carefully and starts going down on me. I can hear his teeth hitting my clit ring, and that turns me on more. During Sandy, I showed him exactly where my G-spot is, and now he begins using this information against me. I come about six times and fall asleep in his arms.

DAY THREE

8 a.m. Wake up next to ST, trying to remember how I even got to his apartment. We didn't have sex. I barely went down on him at all. I find this so interesting, as I love giving. Plus, I fundamentally thought blue balls could kill you till I was 19, but ST was perfectly content and happy. Wake him up with a blow job for being amazing, but he never comes, as he only comes through sex. I'm not sure why we don't have sex, but I have to run to work and so does he.

9 a.m. Think about my date with SB the entire subway ride to work.

9:20 a.m. Passing building where SMM works. I'm wet as I enter my office.

10 a.m. Text from SB telling me had a nice time. I reply that I did, too. I like him.

Noon: EBBF won't stop messaging me. He keeps asking if he can come over to touch my boobs. I've entered high school.

2 p.m. Just realized I have a date tonight with a Tall George Costanza look-alike that I sort of forgot about. No butterflies. This depresses me.

3 p.m. I read over SB's text message to me. Contemplated canceling date with TGC but decide to keep it as a suitable distraction from SB.

7 p.m. TGC comes by my office to pick me up, and we head to a bar downtown. He's pretty animated, and I immediately think I'm in some Seinfield episode. I question silently if this is a date or just two friends hanging out. At the bar, he takes off his coat, and I realize he's more overweight than husky than I had thought the night we met. I wonder if he has a big penis. I wonder how he has sex with such a big tummy.

9 p.m. TGC is much older than he looks, about fifteen years my senior. I thought he was about seven years older than me. Nonetheless, he has an excellent personality, which makes me almost look past his weight. Our conversation has swayed to our past sexual experiences, and I get the sense that he is incredibly dominant and generous in bed. If there was any question if this is a date, there is no doubt any more. This is a date. He is into me.

11 p.m. Hop into a cab with TGC, and he takes me home. Awkward hug in the cab. We both have a dinner party to go to the following night with mutual friends, so we agree to chat tomorrow.

11:30 p.m. The whiskey is getting to me. I'm horny. I read over that one silly message SB sent me earlier in the day. Why am I hung up on this guy? I masturbate twice to porn that incorporates many men and bondage. Then I fall asleep.

DAY FOUR

7:30 a.m. I wake up from weird and twisted dreams about nothing. I wake up by masturbating to an amateur video of a woman tied up and blindfolded and her boyfriend teasing with various sex toys.

10 a.m. Thinking about SB. I wonder if he has a nice penis.

12:20 p.m. On the way to lunch with a friend who knows nothing about my group-sex fetish, COF messages me asking me when our next play time is, as he has several men that want to play. I respond with "I don't know right now," because I don't! Yes, I like that certain element in my life, but I also want a steady relationship. Part of me believes that my next boyfriend should share this with me, but I get the feeling that most guys who are in this lifestyle aren't looking for something serious or steady. A couple years ago, I had a boyfriend in this lifestyle, and our relationship was so much fun. I liked going to parties so much more as a couple rather than as a single woman. At the very least, I'd like to meet someone who is simply open-minded and equally loyal. Does this guy exist?

2 p.m. TGC messages me to tell me he had a great time. I respond with "I did too. See you tonight!" I'm leading TGC on by being nice.

5:38 p.m. About to leave office, and I kill time updating my secret smutty Tumblr. One of my favorite hookup buddies messages me to tell me that he loves the new updates I posted and says he wants to only have anal next time we meet. I get very aroused.

8:30 p.m. I go out to event with my friends, and TGC is there as well. Our friends don't know we went out, though I do confide in one of my closest friends there about our date. He makes it very obvious that he likes me. Asks if we can hang out next week, after I tell him that my weekend is fully packed, I smile and say, "Maybe." Doubtful though.

DAY FIVE

8 a.m. Heading to the office early for an important early-morning meeting. Per usual, I think about SMM as I pass the cross street of his building.

2 p.m. Stressed out at work. Usually my brain would wander over to sex by now, but I've been consumed in an Excel spreadsheet.               

3 p.m. Dom Lawyer Friend Gchats me to tell me about this girl he is hooking up with. Barely listening.

5 p.m. OkCupid Guy contacts me, confirming plans for our date tonight, which I completely forgot about. Meeting him at seven.

7:01 p.m. Twenty seconds in, and this guy has already cursed, which sort of takes my breath away in a bad way. He seems to use curses every other word. I contemplate leaving.

7:15 p.m. We go to a hole-in-the-wall restaurant, which I think was more or less selected by him because it's cheap rather than the fun experience of going to hole-in-the-wall restaurants. Still contemplating my escape.

7:30 p.m. OkCG is cute, but crazy intense and incredibly defensive. Our conversations stall a lot. He's being a dick.

8:15 p.m. He pays for dinner but says, "You owe me," with a smile.

8:30 p.m. We go to a bar down the block and order two drinks. Again, bar is a dive (I don't belong here, style-wise) and only picked because drinks are cheap. Drinks come, and he actually does expect me to pay. He reminds me that he paid for dinner in the nastiest manner possible. I pay for drinks. I drink my drink. I make an excuse to leave. Intense and super-defensive, OkCG gives me an earful. I'm not sure what to say. I stay, but more or less because I just don't want to go home so early on a Friday night.

9 p.m. After he demands I buy the next round, I go home. In the cab, I think of SB and SMM the entire time.

10:35 p.m. I masturbate to a gang-bang video and head to bed early.

DAY SIX

3 p.m. Day has been filled with a business brunch, business lunch meetings, and work … on a Saturday! I'm asexual.

10 p.m. Girlfriend calls me, asks if I would go on an impromptu double date with her friend's friend. I ask for a photo. HOT GUY. Yummy. Okay!

11:15 p.m. I join my friend and HG and his friend. I can't tell if he's into me from the get-go. I think we are both sizing each other up.

Midnight HG is visiting from Europe for the next two weeks. He's dumber than me but has pretty advanced interpersonal skills, which make up for this. Plus, he's hot in a really obvious way. We never get a chance to chat alone, as the conversation is very much a group effort.

2 a.m. We exchange numbers. We make plans to hang out soon. European tourist in NYC? With me? I'm certain we will hook up. He keeps asking me if I want to get married and have children. I'm taken aback by this statement. I tell him that I am not thinking about stuff like that right now, as it's not a priority in my life. He presses on, asking if I'd see it as a priority in three years. I'm confused by the questioning of my priorities. We drift apart a bit for the remainder of the evening.

3 a.m. As a group, we all walk toward my apartment, where I say good-bye to everyone as they go on their way. HG gives me a very intense departure hug and says he's looking forward to seeing me next week.

3:05 a.m. I pass out.

DAY SEVEN

7 a.m. I wake up from a kinky dream where I was playing with a woman's clit with my tongue. I really want to have a threesome now, but I'm too lazy to find an awesome couple that would be game.

9 a.m. Back in the office for a huge work project due on Monday. I am again asexual. HG from last night has requested us to be friends on Facebook. I reluctantly accept.

9:35 p.m. I finally get home. I pass out before even taking off my makeup.

TOTALS: 3 dates; 1 act of oral sex received; 2 acts of oral sex given without orgasms; 3 acts of masturbation; 2 postings on secret Tumblr.