Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the 34DDD Teacher Pretending to Be a Hotel Maid: Female, teacher, Astoria, 27, straight, in a relationship.
9:42 a.m.: Wake up to live-in boyfriend’s hand grazing my stomach. I know what he wants, but I’m tired. Kiss him on the lips and roll over.
12:13 p.m.: Wake up alone. BF has gone to work. Feeling guilty about not pleasuring him earlier. Wonder if he jerked off. Decide I will make it up to him tonight. Ponder ways to make it exciting — new position? New outfit?
7:50 p.m.: G-chatting with boyfriend. Tell him I’d like to make it up to him tonight. He wants us to pretend he’s coming to my apartment for the first time. We like to fantasize a lot.
8:32 p.m.: BF’s birthday is coming up. We’ve been together for almost three years and each year go to Atlantic City for his birthday. He loves to gamble and I love to look pretty next to him. Looking online at Victoria’s Secret and Frederick’s of Hollywood for some slutty lingerie to surprise him with. Once we pretended that I was a hooker arriving at his hotel door in a tight, red, lacy number. Thinking of how to change it up this year: Nurse? Policewoman? He once said he’s not into the nurse thing, so maybe I should be a hotel maid he walks in on?
9:33 p.m.: BF should be home soon. Put on his favorite black string thong under my white, eyelet sundress and await his arrival.
9:45 p.m.: BF comes home. I’m watching TV and invite him to join. Eventually we start making out, which leads to various forms of foreplay. As I straddle him in only my thong, he pauses and asks if I’m sure I want to do this, sticking to our fantasy of it being our first time. It reminds me of when he asked me that before we did it for the first time and I almost come on the spot. Needless to say, neither of us lasts very long.
12:02 p.m.: Wake up alone again. Live-in boyfriend has gone to work. Dreading September when I actually have to be up at a decent hour.
3:30 p.m.: G-chatting with boyfriend but I have get offline so I can go for a run. Just bought a cute leopard print bathing suit from Beach Bunny for our trip to AC. It seems to be the only place that I can find sexy bathing suits that actually fit my 34DDD chest. BF thinks those are my best features, aside from my blue eyes.
3:34 p.m.: BF texts me to send him a picture. He likes the way my boobs look in my black sports bra. I take a quick snap of just my chest in the elevator and send it off asking for a picture back of his reaction.
3:37 p.m.: BF sends me a picture of his boner. I reply and promise to take care of that later. Time to run.
5:40 p.m.: A dozen sunflowers arrive at the apartment. They are from BF. I’m so happy he still has a romantic side. Card says “I love you.”
12:45 p.m.: BF comes home late from work. He always looks hot in his Ralph Lauren polos. They accent his best feature — his strong arms. I’m not in the mood for much, so we make out a little and I give him a blowie. I pay extra attention to his balls with my tongue. By the sound of his moans and the speed of his orgasm, his reaction is positive.
10:37 p.m.: Wake up with BF. First thought: My lingerie better come today. Leaving for AC tomorrow morning. I ordered a black, lacy apron baby-doll with black thigh-highs. Going for a sexy maid look.
3:45 p.m: No mail yet.
7:30 p.m.: At boot camp class doing squats. Can’t help but think about being on top of my boyfriend in this position and getting turned on. I love being on top where he can see and touch me all over.
9 p.m. Home from boot camp and a Victoria’s Secret package is waiting for me. Immediately try on the new getup. I was a little nervous about trying the backless apron baby-doll, but am pleased that it is very flattering on my stomach, and gives me amazing cleavage.
11:25 p.m.: BF is still not home from fantasy football draft. I can’t wait up any longer. Shoot him a sext about how excited I am to ride him at the Water Club and pass out.
8 p.m.: Wake up with BF. Make egg white omelets and pack our bag while he works out. The sun is shining and I can’t wait to show off my new bathing suit at the pool.
12:15 p.m: Arrive at the the Water Club and it is raining. We head up to the room and immediately take off our clothes and make out in bed naked. Within a minute, BF is poking his boner into my thigh. Immediately get wet knowing how much I turn him on. I get on top of him, putting my arms on his chest to hold myself up as well as squish my boobs together, a view I know he enjoys. We’ve obviously both been looking forward to this so neither of us lasts long, but I’m cool with that. There will be plenty of other opportunities I’m sure.
1 p.m.: Order room service in our robes. The truffle fries at the Water Club are orgasmic.
2:30 p.m.: Watching TV and cuddling while BF strokes my boob. I follow suit and tease his inner thigh lightly with my fingers. Very soon I want him inside of me. He gets on top, throws my legs back over my head, and thrusts so hard the bed is banging against the wall. I tell him I want him to come on my tits and he immediately pulls out and does so.
7 p.m.: After some gambling, BF and I head back to the room to get ready for dinner. I hop in the shower and call for him to join me. He comes in, sits on the shower bed, and pulls me on top of him from behind. Sex in a shower can be tricky, but is made much easier when a bench is provided. Still, my legs are hurting after a few minutes. Damn boot camp squats. I turn around and straddle him, ensuring my tits are all over his face. I wasn’t in the mood at first, but as his hands travel from my back to my ass up to my boobs, I feel myself getting extremely turned on. I tell him how much I love his hands on my tits and ass. He squeezes and licks around my nipples until I can’t wait any longer. He finishes very shortly after. Another plus of shower sex — no clean up required.
1 a.m.: Heading up to the room after a few hours of blackjack. BF is still playing, but I want to doll myself up in my new lingerie. I slip into the backless, black apron lingerie and hoist my boobs up and together. I decide not to wear any underwear so when I turn around my boyfriend will get a great view of my bare ass. I put on the black thigh-highs and heels and when I look at myself in the mirror, I’m actually quite turned on with what I see. While I’m touching up the curls in my hair, the doorbell rings and I know it’s the birthday boy. I open the door and playfully tell him I’m almost finished cleaning the room. As I turn around to walk towards the bed, I hear him moan and know he likes what he’s seeing. I get on all fours and he immediately throws off his pants and comes up behind me. He rubs himself against my crack. I turn around and start giving him a blowjob. Eventually he lays down so that we can 69. I’m a little drunk and can’t feel much down there, so I decide we just need to get this over with. I lead him to the couch against the window and push him down. I straddle him with my heels still on, shoving my tits on his face as I grab them, moaning. I know he loves to watch me touch myself when I ride him. I whisper in his ear how much I love feeling him inside me. He comes immediately, with his hands on my ass.
9:30 p.m.: Wake up early in the hotel. BF is still sleeping. Watch a little TV and then get bored and tug at his dick to try to get his attention. He moans and rolls over. Get ready to check out.
12:50 p.m: Driving back to the city. I always get bored on the long drive and decide to make things interesting. I lean over to BF and lick his neck as I put my hand on his crotch. He tells me not to start something I can’t finish as he unbuckles his khakis. I’ve never done this before and am both excited and nervous. I threaten him that he better stop me if a semi-truck goes by. I start to jerk him off as I suck on him. He’s so excited that he lasts maybe three minutes. Thankfully, he is able to control his legs and orgasms without causing a scene or accident.
1:15 p.m.: Pull over at a rest stop. BF forgets his shorts are unbuttoned and unzipped. His pants fall off as soon as he gets out of the truck. Hilarity ensues.
12:30 a.m.: Out at a lounge for a friend’s birthday in Tribeca. BF and I are dancing at the table and I’m watching my friend’s younger sister. She is single, blonde, and gorgeous. She’s dancing/making out with an older guy she just met. Love her outgoing personality, but as I dance with my BF I am reminded of how thankful I am to have him.
11:45 a.m.: Wake up slightly hungover. Going to brunch with BF’s family for his birthday. As we scramble to get ready, neither of us is in the mood for anything sexual.
5:20 p.m: Back in the apartment. There is a hurricane approaching NYC tonight so BF and I are trapped in our apartment. I’ve been paying so much attention to him lately that I now want some attention. He’s playing FIFA Soccer on the Xbox and I cuddle up to him, kissing his neck. He tells me to wait just a few minutes, but I can’t. I take off my tank top and my shorts and straddle him in just my black lacy bra and matching Hanky Panky thong. He can’t resist. Video game is off and he’s laid me down on the couch and wrapped us in a blanket. He’s licking my tits while I jerk him off. I move his hand down below my thong, hinting at him to finger me. There is nothing that turns me on more than making out with my boyfriend under a blanket while he fingers me beneath my underwear; it makes me feel so young and naughty. I stop him just as I can’t take it anymore and climb on top of him. I’m straddling for maybe a minute when I come. I let out a moan and tell him I’m coming, which in turn makes him come. I love simultaneous orgasms.
9 p.m.: Make BF his favorite ravioli with pesto sauce for dinner. We open a bottle of wine and cuddle on the couch, listening to the rain and the wind outside.
11:15 a.m.: Wake up slightly hungover. Thankful we still have power. Hop in the shower in case it goes out.
5:45 p.m.: Dinner at a Mexican restaurant with BF. He orders a beer and I love that he is relaxing. We don’t get to unwind much due to his crazy work schedule, so this has been a special week since he took time off for his birthday. Wining and dining on a Sunday night reminds me of when we first started dating.
8 p.m.: Cuddle on the couch with BF and watching Jersey Shore. Eventually fall asleep in his arms.
TOTALS: six acts of sexual intercourse; two sexy pictures transmitted; two blowjobs, one in moving vehicle; one sext sent; one 69 session.
Would you like to take part in the glorious tradition that is the New York sex diaries? Just send an e-mail to firstname.lastname@example.org with your contact information and why you think you’d make a good diarist. If you’ve got what it takes, we’ll be in touch!