West Side Stories

I am over forty and my boyfriend of almost 8 years left me last year. He was cheating on me with a married friend for a year before he broke up with me. It was brutal. I thought my life was going to be over. Not end, just be over. I was petrified of dating again and convinced I was too old to try. 

A year later, I am leaving the apartment of a 30 year old personal trainer who worshipped me from head to toe, then took me bent over the side of the sofa.  He’s been texting me twice a week to come over and fuck. That’s all it is, and I’m down with it. I have never even spent the night with him. 

I can honestly say, I have never been fucked like this in my entire life. His dick is fat, but even beyond that, he is a conscious lover and an expert in female anatomy. He knows where the clitoris is and how to stimulate it. He makes me come until I'm practically sobbing. When he gets me there he says something hot like
-That’s what I was waiting for.  Oh Yeah, that’s what I want. 
It makes me come even harder. 

On my way home, I get a text from Janet.

-Come to Obrien’s.

Janet is a friend I got in the “divorce.” She wasn't having me crying in sweatpants, so we started going out most weekends and meeting guys. We have a breakdown of where we go and how much time we spend at any one place. If we see there is no potential, we leave without a drink. We order one drink and one water at each bar we deem worthy to save money and to make sure we don’t get drunk too fast. Janet and I work on so many levels. 

I park in the back of O’brien’s. She is outside smoking with a tall dark haired guy who looks vaguely like he is in a Twilight movie. I don’t smoke, and I find the wait time for smokers intolerable. I tell her I’ll be at the bar and go in the back door. 

The place is packed tonight as there is trivia or something boring that everyone loves. I’m mad Janet made me come here on a busy night, right after I got fucked within an inch of my life, and I could be at home, alone with my oxytocin, rolling over the memories. And now she is outside talking to the young vampire and I can barely get to the bar. I finally do though, and order a beer. While I am waiting a young woman tries to squeeze in and I kindly let her saddle up next to me. 
She immediately begins to tell me how she and her boyfriend are polyamorous. They have been together for five years and it was this or break up. She thinks it is going well, but it is complicated too. They have rules. It is a whole open communication agreement. In order to make the PA lifestyle work, you must communicate hopes, fears, anxieties, wishes, boundaries. 
She looks me in the eye and I wonder if she is trying to pick me up. Maybe to take home to her boyfriend or for herself, I am not sure. I bring up my last relationship, and how when I suspected he was having an affair, I wanted to go open relationship, but he was in denial. Her eyes flash in a little eruption of anger and empathy. Maybe I am interested in her. She looks so cute with a brown bob and orange lipstick. How old is she though? 28? How old does she think I am? 

She is with a male friend from work (that she is not sure if she is on a date with or not) and her live in boyfriend. She invites me over to talk to them. This seems like it could get complicated.

We start out by playing trivia and really trying to find the answers. Janet eventually comes in, but stays by the pool table making out with her dude. The four of us are deeply invested in the game. We all search inside our minds to pull out the answers that may be just floating around in there. We move our bodies closer so we can whisper to one another. The friend from work puts his hand on the small of my back while he says the answer in my ear. I can feel his lips touching my hair. I think of what happened twenty minutes prior. My knees get weak with the flashback. Me on top of my young lover, with one of his hands around my throat, squeezing, and the other pinching my nipple. I smile in a dreamy way and the man in front of me assumes it is for him. He responds with happy eyes and a slight grin. I wonder if I  smell like sex.

I must be giving off something because soon the girl is touching me at the waist and saying what a beautiful body I have. In my ear, like it’s an answer, so the boys don’t hear. 

I excuse myself to go to the bathroom, and she follows me. It’s like a real bathroom with a door not stalls and she comes in and watches me while I pee. A little weird, but ok. She has had a few drinks. Then I get up and pull up my panties. She puts her hand on the side of my hips and comments on my round ass. She slides her hand up my naked hip to my waist. I am vibrating all over. My crotch is dripping wet and still sore from the pounding it endured not an hour ago, but I want her to continue. She brushes her nails against the outside of my panties and acts like it was an accident. Laughing coyly, she says she has to pee too.

We switch positions and I see that under her clothes she has on an elaborate black contraption that straps around the belly several times. She lifts up her shirt to show me the bra part, isn't it pretty? It goes on with a series of snaps and would I please help her unsnap some key areas that would make it easy for her to let her panties down? I help her unsnap a few straps around the crotch. I can feel humidity coming from her. I let my hands drift up her torso, and run my fingers  lightly over one of her full breasts. Her nipple tightens up visibly. We both giggle. She puts her hand around my head and asks if I would like to see them. I say yes I would and she pulls them out of the cups of her lingerie to wonderful effect. They are truly perfect and I cannot help but ask if I can touch them. When I put my hands on them, she pulls my face into suck on them. I take one after the other in my eager mouth as my cunt is screaming in my panties. She sighs and pushes her crotch against my leg. Then a knock comes at the door and we know people are waiting to get in. I give them one last kiss and kiss her on the lips, lightly so I don’t ruin her lipstick. She finally pees and we leave the bathroom to the next couple of drunk girls heading in. 

Janet is waiting for me at the bar, and I leave the girl to her two boyfriends, promising I’ll be over in a moment. Janet dramatically grabs me by the elbow and says we have to get out of here right now. Vampire’s girlfriend is going to show up and there will probably be a scene.

I see the girl with the bob briefly before I go. She is disappointed that I am leaving, but she is here most trivia nights with her boyfriend or one of them. She pulls me in by the waist and hugs me with her breasts fully pushed up against me. The men are watching with interest. I bet she fucks them both later thinking of this moment.