I'm not here to complain, things are difficult everywhere and it's not getting easier for anyone. But I do feel like the things we were told when we were younger about living in a society based on merit are a little questionable at this point.
In my experience, and that's what I want to talk about today, the person I am on paper isn't always good enough. I have a job, but it's not a great job. I have a degree, but it's soft and only really puts me in a great position for a Master's Degree, not really career advancement per se. So when my landlord didn't offer a new lease and I had to move, Boston real estate was not exactly open to my situation. I had to look for a single room sublet in someone else's apartment and my credit rating and the amount I could afford were not promising. So I improvised.
I am 26, my financial situation is not prosperous, but I know that no one is too curious about that when I walk into a room. I'm not a supermodel or really all that conventionally hot, but men have always responded to me. High school me would have said that my hips are a bit too big, my boobs too big to be perky or be totally modest without some work, and my lips are bigger than looks good on my face. My hair is brown and curly, and I have kind of a plain face. Nothing about me is outstanding. But men respond. I worked my way through school waiting tables, and found that my flirting was better than my food running, so I worked it. And now, looking at my lease ending in two weeks, I'm scrambling to use everything I have to find a new place.
I'm not trying to hook up for a place, that's just dumb. I don't want to be locked into a situation for the next couple of years and feel like I have to perform in order to keep up my housing, that's just too much pressure. But I figure I can sell the "possibility" lightly to get me in the door and then keep to myself.
It's a good plan, but the nuance is hard. I don't want to promise anything, but I also can't live with someone totally into me. I am a modern woman, and I like to fuck. I don't want to always go to some dude's house, that doesn't always feel great. So I need to find someone who kind of likes the idea of me in their private space, but also understands that I'm going to get my needs met. I don't feel like I'm ready to have a boyfriend again, just need a guy here and there to keep my balance.
I've gotten more insecure about housing as this last month has passed, but I feel pretty confident. But this all leads up to Tom and his apartment. He asked me over to see if we're compatible as roommates, and I came by after work. I changed from my flats to heels, and took off my blouse so I was just in my sweater. It was tight enough to suggest my body, and slacks in general tell you everything you want to know about my hips and ass. Tom invited me in and we talked at the kitchen table.
He gave me the creeps at first. He looked like he was around retirement age from some trade, a big stiff belly and big hands, and definetly felt lonely; he looked at me like he wanted to see more but knew he wouldn't. It was kind of ideal. But as we talked, I realized I kind of liked the attention from someone who understood that I was not going to satisfy whatever was going on. But we got along pretty well and both of us like keeping to ourselves, so he invited me to move it. I handed him an envelope of first and last and I moved in the following weekend.
I wasn't wrong about Tom. He was hungry, but didn't make it obvious and that was great for a couple of weeks. About three weeks in, I was out with some friends and met someone at one of those grown up arcades when everyone gets drunk and gets progressively worse at air hockey and video games while getting hotter in the well-lit space.
Jason worked somewhere I can't remember, but he was fun and he had a nice ass. He was charming and just interesting enough that we know someone was going home with Jason. I caught Jason staring at my chest while one of my work friends told a story and made my decision. I turned to him and he looked up quickly to hide what he was doing, but I just smiled and I think that's when he made his decision, too.
We decided to go back to my place because it was closer, and when we came in Tom was in the next room with the TV just a bit too loud, which was perfect. I led Jason into my room and he pulled me close and kissed me. I held his ass in both hands and pulled his cock to press against me through our clothes and rubbed against him. HIs hands went under my sweater and unhooked my bra and I could feel how excited he was as he slid his thumbs under the cups and brushed my nipples.
I knelt down and opened his pants and put his cock into my mouth immediately. I love giving head, and he wasn't so big I couldn't fit him all the way in. I sucked in slowly, all the way in, then back out until it was just his head, and then back in, guiding his rhythm by pulling his ass to me. After a few minutes, he pulled my shoulders and I stood up and we took our clothes off. I lay down while he slid the condom on, then he held the backs of my thighs with his thumbs on both sides of my pussy, and slid himself in. I was very wet, and I really needed to get fucked. Jason was confident, he was gentle, and he was good, but he came first. I felt his breathing change, he sped up, and then he pushed himself up in me so hard my ass lifted of the bed and he just held himself in there, just little jerks until he finished and rolled off of me. He quickly pulled off his condom, tied it, and dropped it on the floor and then started sucking on my nipples like he'd wanted to all night. He started to finger me with his middle finger deep in me and his thumb pushing down and rubbing my clitoris. I came twice before he was hard again, and then I pushed him on to his back and laid next to him and sucked him until he came, and I kept sucking until I was sure he was done and I swallowed. Twenty minutes later he was dressed and leaving and I noticed the TV was off. I hoped I hadn't disturbed Tom, but also, I couldn't not fuck. I have a pretty healthy sex drive, and I really like being desired and making someone cum.
When I got up the next morning, Tom was making coffee. The kitchen was it the middle of the apartment, Tom's room on one side connected to the living room and mine on the other connected to the kitchen. We met most mornings in the kitchen, neither of us apparently morning people, so not talking much.
"Morning, Tom."
"Oh hey, I didn't see you come in."
Our kitchen wasn't big enough for a table, no one is getting lost in there. Obviously, Tom was uncomfortable.
"How was your night?"
"It was good. Did you have fun with your friends?"
"Always, yeah. I met someone, I'm sorry if we made too much noise. I hope that's not awkward."
"No, nothing wrong with that."
That was our only interaction about it. Tom seemed pretty normal with it, so I stopped being weird about it. Normal is hopefully one to two times a week, mostly with a couple of guys I've known for a while. I'm not a big fan of the drama of meeting someone and then trying to navigate as little actual social interaction as possible for both of us to get what we want, so I try to avoid that.
About a week after Jason, my friend Mark came by. Marky and I have been friends since high school. We tried dating in our sophomore year, but it got old pretty quick. He was a big military guy, enlisted midway through our senior year and ran off like ten minutes after the final bell, and our politics and opinions never really aligned. But I was 16 for a minute, and do you remember 16? Horny for no reason, and by the time I was ready to try something, it was pretty clear Mark and I were about done; so I decided to give him a blow job. It wasn't a great blow job, but it was a first for both of us. We were doing homework at his house, and no one was ever home during the day. So I closed my book and just got on my knees in front of him and started to unzip his pants. He said "what are you doing?" and I said "I want to suck your dick" and he said "are you serious?!" and I said "Mark. I'm your girlfriend and I want to suck your dick and I've wanted to for a long time." And I had. Mark was a pretty average size, but he had a great big head and came a lot. I mean seriously a lot, like hard to swallow it all before it drips. And with that big, round head, he had a great dick to suck. We didn't socailize and we didn't fuck, he'd just come over and I'd give him head. He's been engaged for years but he thinks getting a blowjob isn't cheating, so I still get to give him head every couple of weeks. We tried anal a couple of times when he first got out of the service and wanted to try it, but it's always been about head.
When he first came over, I was late. But Mark was in the kitchen talking to Tom, just casually chatting. I walked in and said hello, and he turned to Tom and said, "Excuse me, we need a moment."
He walked into my open door and sat on the bed and I followed and shut it behind me. He stood up and pulled his pants down and took off my blouse while I knelt between his legs. He ran his fingers through my hair, grabbed my head, and took control of his blowjob. I looked into his eyes and sucked him like his dick was the only thing in the world. I love sucking him slowly, deep throating him to the balls, but he made me suck faster tonight and he came quickly. I had him all the way in and he came into my throat. I choked a bit while he gave a low moan (or an aggressive sigh?) and jerked him off all the way off in my mouth.
Within fifteen minutes, Mark was walking into the kitchen and then out of our apartment. Tom was still leaning against the counter, apparently looking at a magazine. I came in to get some water and we talked about really nothing at all and then I went into the bathroom. When I got in I was horrified to see that the tank top I'd put on quickly was pulled a bit to the side and my nipple was out. Tom seemed more attentive than usual...or was I imagining it?! I wanted to find out.
I made sure I was still exposed. I think I've mentioned, my boobs are basically huge. They always kind of fight their way out if I'm not wearing a bra so this was easy. I walked back over to Tom and continued the conversation. For the next 20 minutes, we talked about common things needed for the apartment, about the new grocery store, and about the placement of some shelves for the hall. Tom did not obviously look at my nipple. But I could see the movement out of the corner of my eye as Tom's pants got a bit tighter and I could see that he was hard.
When I got back to my room, I was absolutely soaked. I always masterbate when Marky leaves, there is literally nothing hotter than a mouthful of cum. But when I pulled my dildo out of my drawer and immediately slid it in, I imagined Tom walking in on me, being shocked and embarrassed and running out, and I just kept cumming.
Over the next two weeks, I experimented some more. I didn't want to have sex or touch Tom, but I was really getting off on the attention. My bathrobe is a bit revealing, so I haven't really worn it out of my room too much. Once or twice to go to the bathroom or get something from the kitchen, but not frequently. Tom has seen it, but mostly from the other room. So I decided to let him see it a bit more.
