sex diaries

The 38-Year-Old Woman Lusting After a Homeless, Jobless 22-Year-Old

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the 38-Year-Old Woman Lusting After a Homeless, Jobless 22-Year-Old: Female, 38, central Florida, office manager, closeted bisexual, single.


1:30 p.m. Wake up late with a massive hangover. Find PunkBoy soundly sleeping on my sofa, his scarred and tattooed arms over his head, legs strewn about. Despite the fact that he’s only 22, homeless, jobless, and carless, I still want him. Also despite the fact that several months before, we had terrible sex (twice). I watch him sleep for a moment and then decide to make brunch.

2:30 p.m. PunkBoy and I finish our meal. Still groggy from the night before, we ponder what we’ll do. As per usual with PunkBoy, we decide the day will somehow involve alcohol. I offer to wash the tattered clothing he’s been wearing for the last three days and he (thankfully) allows me to do this while he showers. I resist the temptation to walk in on him.

4 p.m. Venture out to one of our favorite dive bars, which reeks of the lonely alcoholic rednecks inside. We order our drinks and I watch him play pool with a fiftysomething man sporting a shirt covered in marlin.

5:30 p.m. We are buzzed and I remind PunkBoy that I have plans for pizza and wine with my girlfriends later. I offer PunkBoy the use of my car while I hang with my friends and he drops me off. Have a great time catching up with my girlfriends.

9:30 p.m. Now drunk on wine, I ask my friends if they mind if PunkBoy joins us for a drink. He arrives and seems to hit it off with my friend, Lips, with whom I’d had a fling the previous year. Lips is a pretty, curvaceous woman with a huge personality. While speaking to my friend across the table, I overhear the undertones of a suggestive exchange between PunkBoy and Lips. I feel a mix of jealousy and horniness.

11 p.m. Lips, PunkBoy, and I leave my other friends to go back to my place. As soon as we get in the car, PunkBoy refers to Lips as “safe,” which is his usual word for a bangable chick. I should have taken advantage of that situation. I’ve convinced myself that, if given another opportunity to get PunkBoy in my bed, it will be better than the first two times. I quietly fantasize about a threesome while Lips and PunkBoy talk, laugh, and drink the much better wine Lips brought with her. I think about how I could orchestrate living out this fantasy in the near future.

12:30 a.m. Lips decides to head home. I walk her outside, hug and then kiss her. Deeply. It’s not like me to make a move like this with a woman, but the threesome fantasy has me quite excited. We promise to talk soon.

2 a.m. I’m exhausted from drinking all day and slightly sexually frustrated. I leave PunkBoy on my couch to watch TV alone and I go to bed, too tired to even think about getting off.


10 a.m. Wake up hungover. Again. PunkBoy is awake when I venture into the living room. He’s watching a cable TV series on Netflix that we’ve recently gotten into. The series involves a lot of semi-explicit candlelit sex scenes. I mean, in every sex scene, the characters are surrounded by candles, which PunkBoy points out to me. We agree that this is super cheesy. I’m unpleasantly uncomfortable watching these scenes with PunkBoy in the same room.

Noon PunkBoy has a friend pick him up from my place. I hug him goodbye and tell him I love him, which I’ve only recently started saying to him. I look at my kitchen in disgust. The countertops are littered with used shot glasses, wine bottles, and remnants of two days’ worth of old food. The mess can wait. It’s a sunny day and I want to get outside. I call my good friend FunnyGuy, a novice stand-up comedian. I arrange to pick him up a few hours later.

3 p.m. FunnyGuy and I head to a beachside bar for beers. We sit outside, smoking cigarettes and chatting about his plans to move to L.A. soon. An ex-boyfriend, The Hawaiian, is sending me sexy texts. I’ve known The Hawaiian for five years and we’ve had a tumultuous on-and-off-again relationship. Still, he’s familiar and comfortable. We’ve been talking about getting together for several weeks but it hasn’t worked out. I try to devote my attention to FunnyGuy, but get distracted by The Hawaiian’s text messages, which are making me progressively hornier.

7:30 p.m. Take FunnyGuy home and think about how to reply to The Hawaiian. I wonder if we haven’t actually gotten together because I’m too hung up on PunkBoy to screw anyone else or if I just really don’t want to go down Hawaiian Road again. One text particularly arouses me, in which he says he wants me on my knees, spreading my butt cheeks apart so he can push his tongue deep inside. Yep, that will do it for me. We send a few texts back and forth before I succumb to my horniness. I lie down on my bed and watch some threesome porn on my iPhone. My mind goes back to my fantasy of having PunkBoy and Lips together. I orgasm six times with my favorite G-spot vibrator, the Ophoria Beyond 1, and drift off to sleep.

10 p.m. Wake up from a dream in which I’m simply making out with PunkBoy. Just thinking about having his sexy pierced lips on mine gets me excited again. I’m legitimately obsessed. This has to stop.


7 a.m. Beginning of my work week. Very uneventful day, except for the ongoing explicit texts with The Hawaiian.


10 a.m. Bored at work. Log onto Facebook and get a message from a young guy who was an occasional sex partner. He recently moved out of state. The sex with him was just okay, mostly because he was allergic to my cat. A runny nose and constant wheezing put a damper on my excitement. Yet the messages I’m getting from him online are getting my panties wet. He tells me how much he wishes we’d had some time together before he moved. The conversation turns kinky. He tells me he fantasizes about me peeing on him in the shower, even in his mouth. This is a game we’d never gotten a chance to play. Pee doesn’t do much for me, but the thought of asserting my dominance over him does.

11 a.m. Read article on famous cannibals in an attempt to curb horniness. Oddly, this does not do the trick.

12:30 p.m. Lunch break. Get a text from Pee Boy telling me to check my e-mail for a surprise. Receive a picture of his large erect penis. Nice. Another one for my collection.

5 p.m. Off work. Home, dinner, TV, bed.


6 p.m. Long day at work followed by drinks with The Hawaiian. Just buzzed enough for him to persuade me to go back to his place. We lie on his bed, drinking more beer and chatting. We kiss and he aggressively pulls my clothing off. He instructs me to get on my hands and knees and he buries his face between my cheeks, which is one of the best feelings in the world to me. The orgasm is so intense, it makes me wobbly. I can’t stay in the position any more. Not giving me a chance to collect myself, he pushes me onto my back and starts thrusting into me. He’s never been so aggressive before and I’m loving it. I tell him I’m going to come and he puts his hand around my throat with just enough pressure to give me the extraordinary combination feeling of slight fear and oxygen deprivation. I am loving this! He pushes himself harder and faster into me and finally collapses his sweaty body on top of mine. We fall asleep.

9 p.m. Wake up feeling slightly groggy. When I realize where I am, I panic a bit and I’m not sure why. Waking up in someone else’s bed is just not my thing. I quickly dress, gather my belongings, say a quick goodbye to The Hawaiian, and head home.

11 p.m. Log onto Facebook. First post I see is a picture posted by PunkBoy’s ex-girlfriend. It’s the two of them together, taking a nap in each other’s arms. My stomach sinks and I fight the burning tears welling up in my eyes. I feel like a junior high girl for being so ridiculously foolish.


6 a.m. Wake up unusually early from a dream in which I’m watching PunkBoy screw his ex. More of a nightmare, really. I try to go back to sleep, but can’t. I lie there and try to push the horrible images out of my mind. It doesn’t work. I give up and get ready for work.

8 a.m. Dreadfully boring day at work. All I can think about is the show I’ll be at later. PunkBoy is playing his solo acoustic stuff. I don’t really care for his music (though I’ll never tell him that), but as always, I’m not passing up the opportunity to be around him. Besides, we have mutual friends who’ll be there.

4 p.m. Close to leaving work. I get a text from The Hawaiian, asking if I want to meet up later. I tell him I already have plans and leave it at that. I know how uncomfortable I’d feel being in the same room with both The Hawaiian and PunkBoy.

10 p.m. PunkBoy takes the stage and begins aggressively strumming his guitar as though he’s torturing it into submission. He sings (rather, screams) into the microphone a song laden with obscenities about drinking whiskey on the beach at night. The small crowd draws nearer to him. I stay seated at the bar.

10:15 p.m. The Hawaiian walks in. He sees me immediately, yet stays on the other side of the bar, a safe distance away. I know he’s upset that I chose this over him. He knows of my limited sexual history with PunkBoy, and I suspect he has realized that my feelings for PunkBoy go beyond friendly. Gossip travels fast in our small town.

10:30 p.m. PunkBoy finishes his set and goes outside to smoke a cigarette. The next performer goes on stage and I decide to make a move toward The Hawaiian. One thing I can’t stand is an awkward situation and I think talking to him will makes us both more comfortable. It does.

1 a.m. PunkBoy leaves with me. He’s much too drunk and cannot find a ride to wherever home was supposed to be for the night. I glance at The Hawaiian on my way out. He looks disappointed.

2 a.m. PunkBoy passes out on my sofa and I go to my bed. Getting myself off with him a mere fifteen feet away from me really excites me. I know that any sound I make will go unheard; he’s snoring loudly. Sadly, the noise disrupts my horny flow and I give up. I fall asleep slightly frustrated.


7:20 a.m. Alarm goes off. Nine more minutes of sleep is all I need before getting up for work.

10 a.m. PunkBoy throws my bedroom door open, hops onto the bed and tells me I’m extremely late for work. Crap. I look at my phone and realize I’ve missed eight calls from my boss. I drink a glass of water and try not to sound as though I just woke up. Screw it. I decide I’ll take a sick day.

10:15 a.m. Call boss and feign horrible illness. Who can argue with stomach flu? I’ve been puking and sitting on the toilet all night, I tell him. I don’t know if it’s because of my guilt over lying, but he sounds slightly suspicious of my story. Nonetheless, he says to text him later to let him know if I’ll be able to make it to work the next day. I thank him for his understanding and hang up.

11 a.m. Send PunkBoy out for mimosa supplies. May as well make the best of my day off. I’m afraid to go anywhere away from home for fear of running into a co-worker and being ratted out. Make mimosas and bagels for PunkBoy and myself.

12:30 p.m. We have plowed through two bottles of champagne already. We decide to switch to screwdrivers and watch movies most of the day.

4 p.m. PunkBoy is falling asleep on my couch. I will have none of this. I snatch the hat off his head and throw it across the room. He looks pissed at first and then starts laughing. He makes a run for his hat and so do I. This turns into a wrestling match, which I always enjoy with him, maybe because it’s the most I can touch him without freaking him out. Also, it kind of turns me on.

6:30 p.m. In the middle of eating the pizza I ordered, I get a call from The Hawaiian. I give him the “bitch button” and finish my dinner.

8 p.m. Text The Hawaiian: “What’s up?” I don’t hear back from him for the rest of the night. PunkBoy and I watch another movie.

10:30 p.m. PunkBoy has a friend pick him up. I’m disappointed he’s leaving, but I’m too tired to try to persuade him otherwise. Off to bed. Have an underwhelming masturbatory session.

TOTALS: One lesbian make-out session; one act of online sex chat; one act of analingus (received), one act of intercourse; two successful acts of masturbation; one failed act of masturbation.

Homeless Lust Sex Diary