I waited a few days before I told Matt—the boyfriend—about my new job at Headlights. Our “relationship” isn’t far enough along that I would consider not working there if he had a problem with it, but it is far enough along that I cared what he thought of me. I was scheduled to begin my training as a Headlight’s girl a week ago last Thursday (I know, I'm always running behind in this blog), so I called Matt up the day before and made sure he was going to be home that night.
One of the many, many rules about being a Headlights girl is that we are not supposed to be seen wearing the outfit outside of the restaurant. Some girls change at the restaurant, and some girls wear sweats over the outfit to get to work. I chose the later, and wore my outfit under my green sweats to get to Matt’s place. I decided showing him was far better than telling him. I admit it, it’s a little manipulative—I’m hoping that after he sees me in the outfit he won’t care why I’m wearing it.
I get at his place a little after 8pm and I catch him asleep on the couch. ‘Law and order’ was playing on the tv, so I grab a remote, turn down the sound, and lean down and kiss him.
“Hey sleeping beauty, wake up. I need to talk to you.” I whisper to him.
He groans and stretches out his arms—then wraps them around me, pulling me to him.
Eyes closed, he gives me one of his grins. “I was having this amazing dream, and you were in it.”
“Oh? What was I doing?”
His grin expands into a full blown smile. “Giving me my birthday present.”
I give him a smirk back. “Keep on dreaming.”
This will take a little explanation. Matt and I have been dating long enough that we’ve actually had a few fights—nothing major, just a few bumps on the road. A few of the things we’ve had disagreements over:
1. Matt is a bit of a slob—worse, when I point out he’s a slob by mentioning all the beer bottles littering the living room; he gets defensive and says I am too uptight. I about killed him the first time he did that.
2. Matt is constantly late to everything. If we make plans to do something, he always shows up twenty minutes late.
3. This is the one that gets us back to Matt’s “giving me my birthday present’ statement. The third thing we fight about is oral sex. ‘Fight’ might be too strong word—we’ve had a few slightly heated discussions. Matt has been very upfront with me; he wants oral sex to be a part of our sexual repertoire, and I…I have a difficult time thinking about having a man’s dick in my mouth. “I thought you were the sexually adventurous type.” He says to me. He of course, has no idea that in the big picture I was already being extremely adventurous by having sex with him in the first place. A year ago I would never have dreamt that I was regularly having sex with a man—and enjoying it.
When I was first contemplating having sex for the first time as a woman, I actually had the thought ‘Well, on the upside, you can have sex and have absolutely no performance anxiety.’ No pressure about being premature, no worries about whether or not my partner is enjoying himself—just lay back and enjoy it, right? Wrong.
Sure, if I orgasm early now it no longer a bad thing—in fact, if I orgasm early now it’s time for high fives because it’s probably going to be a multi-orgasm night, and that tends to make everyone happy.
No, as a woman I have new and different anxieties to deal with—like whether or not I should give my boyfriend a blowjob. Matt and I have talked the subject to death and at one point he had worn me down. I went from ‘no’ to ‘not right now’. Later we bring it up again and this time he tries to corner me with a ‘when’—frustrated, yet wanting him to be happy, I threw out ‘maybe on your birthday’. Big mistake on my part--Matt has chosen to ignore the ‘maybe’ part of the statement, and his birthday is a couple of weeks away. I know this because he keeps reminding me.
Sorry, I’ve gotten way off subject; blowjobs are something I’m feeling a lot of angst about. I can’t decide if I’m making a big deal out of it or not—I mean, before I had sex as a woman I didn’t really want to do that either; now I look forward to making love to Matt. Maybe oral sex would be the same way; then again, most of the women I dated as Jake wouldn’t consider oral sex, so maybe I’m not crazy.
Back to me and Matt on the couch, me in my sweats covering up my outfit.
“Don’t open your eyes.” I say to him.
Of course the first thing he does is open his eyes. “What’s going on?” He asks.
I put a hand over his eyes. “I have a surprise for you. Close your eyes.” I feel his eyelashes brush the inside of my hand. “I’m going to get up—no peeking!”
I get off the couch and slip off the green sweats, run my fingers through my hair as well as give it a shake of my head, and strike a sexy pose wearing only my Headlight’s uniform. “Okay…you can open your eyes.”
The expression on Matt’s face was priceless. “Oh my god, baby! You look hot!”
I walk back over to the couch as Matt sits up. “I took a job at Headlight’s.” I tell him.
“Wow.” He says, still surprised. “That’s great. You are working again.”
It was exactly what I wanted to hear. “You don’t have a problem with me working there?”
Matt seemed to mull it over for a split second. “Nah. I’m cool with it if you are cool with it.”
Hearing this made me feel so much better. I sat down on his lap, wrapped my arms around his neck, and kissed him.
Matt didn’t need any more encouragement—his hands traveled over my pantyhose covered legs and up to white tank top. He starts to gently knead my breast through the top. It feels good, so I sigh and tell him so. We get back to kissing for a few minutes until with his hands move to my sides and he picks me up, setting me on my feet—he is so strong he picked me up like I was nothing. He gets off the couch as well and standing there he pulls down my brightly colored shorts and lets them fall to my feet--I kick off the tennis shoes and socks and then do the same to the shorts. I start to go to remove the white tank top, but he stops me.
“Leave it on. I like it.” He says.
I close the distance between us and reach for his belt, unbuckling it and removing it. He was wearing button-fly jeans and I loosen the pants allowing me to reach in and massage his dick with my hand. I may have issues with the idea of sticking it in my mouth, but I had no problem touching it. We kiss like that, my hand massaging his dick, his hands massaging my pantyhose covered ass. He starts the slide the hose down, stops when he gets it down to my thighs, and brings a hand around and starts rubbing the area around my clitoris. I felt so good I laughed with pleasure.
“Let’s sit back down so I can get these pantyhose off.”
Matt quickly looses his clothes and returns to the couch. I sit back down on his lap, my back resting against his chest, and carefully remove the pantyhose. Matt reaches around me—one hand is up underneath the tank top teasing a nipple, the other is between my legs his fingers doing amazing things. He entered me while we in that position, taking me from behind—I was being bombarded by sensations from everywhere. As he thrust in and out of me he continued to tease me with his fingertips. I reached behind myself, laying my hands on him—I just felt a need to touch.
“Harder.” I gasp. “Faster. Fuck! Just more! Oh baby, that feels so good.”
His speed increases and I arch my back, the back of my head resting against his chest.
He got both hand on my boobs now, cradling them—he runs his thumbs over my nipples. It makes my shiver.
I feel the now familiar feeling building up inside me. “I’m close.” I tell him.
“Good. Because I’m close too.” He grunts.
I start rocking back and forth, adding to our rhythm—and that all it takes. I beat him to the finish line by like a second or two. I shake with pleasure, laugh out loud, and collapse back into Matt’s arms.
We gather our selves for a moment until I break the silence. “So, no problems with me working at Headlights?”
“Baby, if I can get you to wear the outfit for me from time to time, you’ll get no complaints from me.”
It was just what I wanted to hear.
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