sex diaries

The Female Architect Who Cries After Sex With Her Transgender Boyfriend (in a Good Way)

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the Female Architect Who Cries After Sex With Her Transgender Boyfriend (in a Good Way): Female, architect, 38, Williamsburg, queer, in a relationship.

6:45 p.m.: Hard day at work; am overtired. The boyfriend’s whole body hurts him, a result of being outdoors doing intense physical manual labor for eight hours in the rain. We head to our favorite date-night stop, Lan Café, otherwise known at vegetarian Vietnamese, usually reserved for Friday night.
7:30 p.m.: Talk and joke around, unwinding from rough work days over vegetarian pho. I ask him to sleep over. We usually save that for Friday through Sunday because we both have needy cats.

8:15 p.m.: He says yes to spending the night, and we walk over the Williamsburg Bridge under an umbrella because it has started raining. I am wearing a tight, form-fitting dress, and he grabs my ass about ten times on the bridge.
9 p.m.: We shower and are both feeling extremely affectionate. He’s on top of me. We get naked and press into each other, which then turns into him slipping on his strap-on with the seven-and-a-half-inch cock. (He’s a masculine transgender male, and we’ve been in a monogamous relationship for six months.) I come first, and then he comes, and as he pulls out I burst out crying hysterically, asking him to hold me as I sob. It’s strange, although I have cried twice before after orgasm with him, but never so hard, and never in my long history of other partners. I realize it is because after all these years of sex with other people, he’s the first person I have been sleeping with that I deeply love who deeply loves me back. Or maybe it’s the Chicago and Foreigner eighties love ballad sex mix we listened to while having sex.
9:45 p.m.: He takes my hand in his and we fall into a post-orgasmic sleep.
10:30 p.m.: He wakes up and makes us sweet-potato French fries by hand. We watch Family Guy and Bob’s Burgers while laying against each other.

7:45 p.m.: We pick up ginger brews, health-food-store potato chips, and I make us a huge salad and roasted Brussels sprouts with truffle oil and sea salt.
10 p.m.: Too tired to do anything more than lay against each other half undressed. I grab his ass in his tight briefs and caress it before I pass out. He is wearing the glow-in-the-dark Star Wars tighties I bought him.

8 p.m.: It’s the first Friday in a while we aren’t having date night. I meet my best friend for drinks and Mexican food while he meets his old roommate. I have one strawberry-chocolate margarita and catch up on gossip. BF texts me asking where I am at throughout dinner, but when I ask him where he is there is a pause and I get pissed off because I know he is already drunk.
10:20 p.m.: BF asks me to meet him at the Delancey. It’s lined with 20-year-old banker types. I bulldoze through the crowd and cannot find him, which just agitates me further. I text him that I am leaving, and he texts me to wait and come dance to En Vogue and Janet Jackson. I am jealous inside, imagining cute girls or guys chatting him up while he sits at the bar drinking. I push through the crowd and leave the bar.
10:39 p.m.: He’s texting me to wait as he chugs his last beer. I thought I would have a few drinks, although I am not really much of a drinker, and he would have a few and we would be on the same level, but it becomes apparent we are not. All I want to do is get into bed with him and make love.
10:45 p.m.: I see him come out of the Delancey. He asks two young bankers hanging around near the venue for a cigarette. He strikes up a conversation; this, along with the cigarette smoking, enrages me further. I snap at him and am sarcastic, and the two newly imported New Yorkers think I am a bitch. I acknowledge inside my head that I am indeed acting like one.
11:20 p.m.: BF grabs my hand and walks me firmly across the street onto the bridge. He keeps trying to kiss me and asks why I’m being mean. He says we can’t walk any further until I kiss him. I finally tell him I don’t want him to be hung-over and ruin our Saturday together, and I imagined cute girls or guys chatting him up and it made me angry. He says no one was chatting him up, he was just getting his drink on. We continue to hold hands while walking. I’m still feeling edgy and put off.
Midnight: He says he wants to go to our friend’s queer bar mitzvah party, which I had wanted to go to all week, but now just want to get into bed and be intimate. I ask him what happened to him telling me he wanted to break all plans so we could spend the whole weekend together?
2 a.m.: I watch Family Guy, trying not to worry about him wasted on the street and the possibility of someone mugging or beating him up. My heart races. I also imagine someone drunk flirting with him. I take a melatonin and some Calms Forte, which does nothing. My heart still races. He sends me some undecipherable text messages.
5 a.m.: He walks in the door. I am in bed still watching adult cartoons pissed off. He has his hand over his mouth as he bolts into my room and I think he is about to vomit, but he tells me he is just shoving donuts into his mouth. He stinks like a brewery and then gets into bed with me and tries to kiss me, holds my hand and curls up against me and falls asleep.

11 a.m.: BF finally wakes up, hung-over and in pain. I wake up with a migraine, knowing that we aren’t going to leave the apartment the entire day. He usually needs to masturbate a few times when he is painfully hung-over. He is checking the weather, which he is obsessed with, and his Facebook. I tell him to please suck on my nipple while I get off with my vibrator. He wants to watch porn, so I tell him to look up a bukkake porn. He only looks at it a moment and then turns his head to suck my nipple and jerk himself off while I have the vibrator running between my legs.
11:40 a.m.: We order in Thai food, then go back to sleep and hope our headaches subside. We wake up a few hours later, watch a documentary on B-Boys and break dancing, one on the atomic bomb and Michael Moore’s Capitalism: A Love Story.

10 a.m.: I make espresso and wait for my boyfriend to wake up. I shower, put on red lipstick and a too-short leopard print/fluorescent orange nightie, get back into bed, and start reading the Sunday New York Times.
11:15 a.m.: He tells me his back is killing him. I offer to rub him down with arnica gel. I rub his back, his legs, his shoulders, back down his spine, and as my hands go down toward his ass, it begins turning me on. I ask if I can massage his ass. He takes down his briefs. I change from arnica gel for his muscles, to a tingle-inducing spearmint body massage bar that melts upon contact with body warmth. I try and coax my finger toward his butt hole, which he quickly denies me access to. He assures me that will never happen. I go back up, knead his ass some more. He asks me if I’m getting wet. I ask if I can massage his front side with the tingle massage bar. He lets me and I go to work on him as I feel him grow hard beneath my fingers I grab him and tell him to suck on my nipples and finger me, which he does. He looks at me, smiles and hugs me while I tell him I want to go down on him now. I do, and he comes quickly as I just did.
11:55 a.m.: When I pull my head up from between his thighs, there is lipstick all over him. We lay together and hold hands.
6:30 p.m.: We head out to a stray-dog benefit at Glasslands featuring the World Famous Bob, burlesque, and bands. We meet up with my sister, who gives us the tickets and drink a few drinks, eat red-velvet cupcakes.
10:00 p.m.: I decide to go home with him to the depths of Bushwick.
10:50 p.m.: He cooks and brings me dinner (something I normally do for him; in fact, I think this may be the first time he has actually cooked for me). I eat and fall asleep.

6:45 p.m.: I am exhausted; he is exhausted and in physical pain from his job. I ask him if he wants to meet up for pho at our usual spot. He does. Knowing I am going to see him even if for a little while helps me get through my intense workday.
8 p.m.: I want to walk over the Williamsburg Bridge with him, but he is in too much pain from working his body hard all day, so we take the train together and hold hands while holding the subway pole. I consider going back with him to Bushwick again but have a work deadline.
11 p.m.: We talk on the phone, then text each other for another 45 minutes about how we wish we lived together and were sleeping next to each other. I miss his cat, too.

10:30 a.m.: BF responds to a friend jokingly saying they are grossed out by my affectionate mushy post on his Facebook wall by saying: Yes, it is gross, why she has to write all this stuff publicly is beyond me. This creates a huge conflict between premenstrual me and BF. I delete all my posts on BF’s wall and we get into a text argument. BF says actually he really doesn’t care that I post mushy things on his Facebook and thinks I am over-reacting about his comment. I tell him let’s take a break and not speak until the next day since he finds my affection so gross. He says he loves my mushy comments, but just doesn’t see a need for me to proclaim them on Facebook.
12:30 p.m.: We don’t talk at lunch like we usually do. I get soft-serve frozen yogurt with gummy bears to quell the rage.
1:30 p.m.: BF says I better stop ignoring him soon.
2 p.m.: BF sends another message telling me I am being fucking nuts. I tell him that he should go back to the last woman he dated who could not emotionally express herself and would never tell him how she was feeling, and that other guys would be thrilled to have a girlfriend so crazy about them.
5 p.m.: BF texts me he is feeling depressed. I feel badly and tell him he can walk over the Williamsburg Bridge with me if he doesn’t talk to me.
5:45 p.m.: We walk together and he smacks my ass and we begin talking. When we get back to Williamsburg he says he is hungry and asks me if I want to make dinner with him.
6:30 p.m.: We get back to my apartment, chop up ingredients for salad, and eat in bed.
7:15 p.m.: Roommate is painting in the hallway near my bedroom. I am in the mood to have sex. I tell boyfriend to close the door all the way. He says it’ll be obvious to my roommate we are about to do it. I lift my shirt up, pull down my bra, and turn up an episode of American Dad while I ask boyfriend to suck my nipples while I put a vibrator between my legs. He tells me to not come loudly, and I orgasm with as little sound as I can possibly make, and then boyfriend wants to get off. I pour lube in his hand and he presses next to me while masturbating himself. I slip my hand down his underwear against his hand and I also try and go a second round with the vibrator with my other hand. Roommate is in the hallway still painting and both of us are nervous little black cat will bolt open the door while we are making out.
8:15 p.m.: BF goes home to be with cat. I go to Metropolitan Bar to meet friends. I feel all love again toward BF post-orgasm, but could use a little chocolate, too.
10 p.m.: Everyone is starting to leave the bar. I call BF and he tells me he loves my mushy messages to him.

TOTALS: One intimate (but not anal) massage; one act of strap-on sex; one act of oral sex, with lipstick (giving); two acts of vibrator use plus nipple sucking (receiving); one post-orgasmic crying session; three walks as couple across Williamsburg Bridge.

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The Female Architect Who Cries After Sex With Her Transgender Boyfriend (in a Good Way)