Lipstick and Other Stories

by Petual Caesar

  The foreplay went on and on and on, each of us taking, then giving, and then giving and taking again. I took her and she begged me to take more, and she took me and I begged her to take more. All of my heart and soul was in every stroke, and I plunged onward, until her shudders let me know she was content.

  Coming In My Back Door

  To Dante

  October 8th

  I know it’s been a few weeks since I’ve written in you. Victor and I have been really busy with wedding plans and just enjoying being engaged. Victor is all that I could ever want in a man.

  We had the anal sex talk again.

  I know I promised Victor that we would once we were on our way to getting married or at least right when we got married. I know he really wants to. I know how much he has enjoyed it in the past with other women. I want to please him more than anything, but I just don’t think I can. Not that I don’t want to. I do. So bad. There have been many times when we’re in bed doing our thing and I want to. I think about it. He’ll be hitting it from behind, driving me crazy. I love that position, especially when I’m really horny. I can really go to work on his dick the way he likes. When it starts to get really hot and wet he’ll whisper, “Can I please try baby? I’ll be gentle I promise. Feel how wet you are? You know you want me to.” Right then I do, and I wish my asshole could just open up to receive him. It’s something I’ve never done, and I’m scared. Victor is not small by any means. I can’t figure out how he plans to fit all that back there without some kind of surgical procedure first.

  *

  October 14th

  My sister and I went to her favorite sex shop today. She’s such a freak, which is good in this case ‘cause I can ask her all about this anal sex stuff. She’s shopping for a new vibrating bullet. I’m trailing around behind her in the store. She’s comfortable no matter where she is. I stop in front of the “personal lubrication” display, trying to look as if I purchase this type of stuff every day. For a moment I watch my sister strut over to the vibrator section and squeal in delight as she picks up “The Great White Shark”. I finally manage to face my fears and the shelf of products that would hopefully help me make my marriage successful. I see the lotions and creams there that are supposed to “ease the occasional discomfort of anal penetration”, “increase pleasure and decrease sensitivity of the anal cavity”, and “create greater pleasure for both by decreasing rectal discomfort”. What in the hell?

  My sis comes over to me. She picks up a small tube and hands it to me. I can’t say a word at first. When I ask her questions about the whole…process…she tells me that quite honestly, it can be painful the first time, that I need to use lots of lubricant, and that he needs to be extremely gentle and patient. She also suggests that I be pretty drunk at the time too. She knows I am really apprehensive about having anal sex and she asks if I am really sure I want to, and if I’m not, to tell him so.

  It just isn’t that simple.

  *

  October 16th

  Last night I stayed at Victor’s place. It was one of our last nights together before the wedding (we’re going to spend a month apart to ‘re-virginize’ ourselves). The sex is so great with him, and the comfort that comes from being with someone I know and love and trust is why I can’t wait to be his wife. After we bathed and got into bed, he began eating my pussy, and pushing his tongue against my ass. I’m so glad I just had my Brazilian. In fact the first time he ever ate my pussy after a fresh Brazilian wax he said “that’s where we’re gonna go on our honeymoon—Brazil!” Anyway, pushing his tongue against my ass was his way of asking me if I’m ready to try. So we did try a little, but I can’t do it. Well, not all the way anyway. The pain is just too intense! It also feels good …the pain I mean. I can’t explain it. I like it but I’m afraid to go through with it. He only managed to get the very tip in, which frustrated him a lot. He tried to hide it though. He went to the bathroom to wash himself, then came back to bed and kept on making love. It was incredible like always, but I can’t help feeling it disappoints him when I can’t give him anal sex like he wants. He wants it bad!

  He told me back in our dating days that he and his wife did it all the time. He didn’t tell me that like he was comparing me to her, or like I had to compete with her. I want to be the best lover he ever had. When I sleep with a man, I don’t want him to ever want another woman after me—that is my primary objective. I’m always successful. All my exes still hover around, trying their hand now and then. Since I’m like that, I don’t like the idea that some woman out there had pleased him sexually in some way I can’t. The fact that they had anal sex often didn’t save the marriage or keep him from falling out of love with her. He tells me he loves me. We’ll take our time. He says he loves all the other stuff we do. He says I’m truly the best he’s ever had. He’s real quick to say that’s not the most important thing of course. Ha ha ha. Hey, he’s a man, so I know it helps that he enjoys fucking me like he does. He says he likes knowing I’ve never done that with anyone else. He gets off on knowing he’s the only man that will ever do that to me. When we talk about it he gets hard. When he’s fucking me, I can always tell when he’s thinking about it. We’re usually doing it doggy-style, my ass up high and spread apart and my head down low like he likes. He’ll be moving his dick in and out of me real slow. He’ll be watching it go in and out, with his fingertips on my ass, pulling my butt towards him when he slides into me, pushing it from him when pulls out. He says he likes watching it come out all creamy. He’ll spread my ass cheeks apart as he goes in and out. I grip down on him, and I can feel his eyes on my virgin asshole. He’ll moisten his finger and place it against my asshole, still moving in and out. I can feel him get harder inside me. I know he wants to put it in my ass so bad in that moment. I think about him in me like that, and start to get wetter. He feels it on his dick and puts his finger in my ass a tiny bit deeper, grinding harder. He’s making me more excited, and I’m making him more excited. It is great until he tries to go in my ass. His dick just won’t fit. He says he knows that I’ll love it once we do it, that I’ll just cum all over the place and that I’ll be begging him to do it all the time. Considering that I cannot get past the head of his dick without bursting into tears, I kind of doubt that.

  What am I going to do? The wedding is less than 2 months away, and I don’t know if I can do this. I need to tell him if I’m not able, ‘cause right now he thinks I am. He’s counting on it.

  *

  October 22nd

  Its times like these when Victor makes his best anal sex arguments. Well, not really arguments, ‘cause we do agree that we want to. We’re going to. It just happens that when I’m on my period, the subject always comes up.

  Victor doesn’t mind doing it when I’m like this. We don’t do it as often, or as vigorously, but he will pull out a towel, spread it across the bed, please us both, then jump into the shower. I give him extra head to compensate. He loves head from me. I truly seem to have a fellatio gift. I can lick the head, suck it, and move it in and out my mouth all at the same time. I can suck him softly and then increase the suction and pressure bit by bit until he grabs my head, fucking my mouth. Then he’ll come and I’ll swallow. I have great technique I must admit…a natural born deep-throater. He said he never knew he could enjoy blowjobs so much. Without fail, at some point during my cycle, he’ll talk about how anal sex would give us “something else to do” during my time of the month. Another option. Another way to please each other. Of course, I look at him like he’s crazy and we laugh about it. I can’t help kind of agreeing with him though. Something about being on my period makes me really horny. He’ll come out of the shower with his towel around him, and I just want to plop my big round ass on his dick and shove it up in me. I think he knows when I’m thinking this because he starts to get hard, and the front of the towel rises up like a tent. I laugh and throw a pillow at him. He likes to flaunt his naked self around me because he knows I’ll more than likely give him a litt
le treat. For the next four to six days, he’s on short rations as far as the pussy goes, but we work around it. I know nothing would please him more than for me to let him take my ass since the pussy is less available.

  *

  November 2nd

  We tried again last night. It didn’t go well. We had gone out to dinner and I tried to have a few extra drinks since he had that “I’m going to get in that ass when I get home” look in his eye. I guess I wasn’t drunk enough. I finally bought some of that ass-numbing cream I saw in the sex store. It’s been on his nightstand for about a week now. When we went to his place last night (we’ll be apart for 4 weeks starting the 10th) that’s all he wanted to do. He undressed me. He had me kneel on the bed. Propped my midsection up on pillows. Kissed me. Played with every part of me. My pussy was soaked and heaving I wanted it so bad. He rubbed the cream all over my ass hole, and I spread myself as wide as I could. Then he started trying to penetrate me. After last night, it’s my opinion that those creams don’t work, because we followed the instructions to the letter and that shit still hurt like hell.

  He always gets a little too excited. He says it so tight back there and it feels so good. I’m sure it is after 33 years of being closed up. I know it feels good to him. With the first inch or so, I’m okay, even when it starts to hurt a little. I swear, I think I actually like that pleasure/pain sensation. I might even moan a bit. That’s when he gets too excited and starts forcing it in too much, too soon. I pull away and he tries to grab me and get me to hold still and I move away again, and at some point he just pushes too far. I actually scream. When he hears that, he always stops.

  I tried backing onto him as he sat on the edge of the bed. No luck. I tried mixing the lubricant with Vaseline. No luck. I took a hot bath, thinking it might relax and loosen some stuff back there. No luck. We tried for about an hour and a half before we fell asleep. We laughed the next morning over breakfast, but he could tell I was mad at myself. He kissed me on my cheek and told me “you know I don’t care right? You know I love you and I’m not hardly worrying about it, right?” I nod and smile, still thinking about it.

  *

  November 3rd

  I’m thinking now that maybe I should tell him I don’t even want to try anymore. I mean, I know I said I would, I know I promised. It’s not like I haven’t tried. I think I get too nervous, scared I won’t be able to control my bowels once he’s done with me. When he gets all excited, and starts moving in for the kill, I get nervous and tense up. I keep telling him he has to get me so excited that I won’t care ‘bout the pain. I mean, he almost cums when we talk about it, so you know when he’s at my back door, he goes crazy.

  I wish I’d done this when I was younger. I had chances, just never did. I used to always joke that I was saving my ass for my husband because it was all I had left to give him that could be exclusively his. Now it’s true. We’re getting married on December 15th, and going to Brazil for our honeymoon. We’re staying there until after the New Year. I don’t feel right about marrying a man I cannot please in every way. I keep thinking maybe while we’re away on our honeymoon, things might work out. If they don’t…I have to know…how will my future husband feel if we never have anal sex? I know he’s used to that from his previous marriage. Even if we try, and he never gets it, will he be mad, or feel like he gave up something that was important to him? I know it’s just a sexual act, and that he’s more than satisfied with our sex life, but I want to please him as much as I can. I want him to experience the beginning and end of me (so to speak), and everything in between. I want him to take all of me and leave nothing. I want to belong to him completely. I need to know for sure that it’s okay if this never happens.

  *

  January 4th HAPPY NEW YEAR!

  We’re back from Brazil, and I’m Mrs. Victor Marshall. Brazil was incredible! I feel absolutely transformed.

  Warm nights. Ipanema Beach. Sugarloaf Mountain. Caramel colored bodies. Tequila. Rum. His chocolate eyes. Cocoa butter in the air, and on my skin. Gorgeous sunsets. Walks all over the beaches. Long kisses. Released desires. Sexy shadows on the wall. Candle wax all over. Exquisite pain, but I didn’t care. Slow, slower, slowest. Even slower still. Moving, barely detectible. Molecule by molecule. Opening. Widening. Resisting, then relenting. Not wanting to want what I want, but I want it. Need it. Not fighting the pain now. Taking it. Taking him. As much as I can. Tears stinging my eyes. Slower and slower and slower. He’s stopping. I don’t let him. Diving headfirst into the rush of sensations. The hurt and the…fullness of him in me. Filled to overflowing. Pouring out, pouring over. The last inhibition washed away. A baptism, a new sexual creature arising for my new husband’s pleasure alone.

  I think I like anal sex.

  Lipstick

  To James

  Stephanie drove to work that Friday morning. As she glanced into the rear view mirror to check traffic, she caught sight of her own eyes, and stared into them for a long time. They were the same eyes she always saw when she looked into mirrors. The same light brown eyes she’d seen as long as she could remember. This morning, they were the eyes of a stranger. She couldn’t focus on them for long before the remnants of the sexual hangover kicked in. She thought about the events of the night before and felt an orgasm well up in her as the mental pictures played themselves out in her brain. She shook her head to erase the images so she could pay attention to the vehicles switching lanes near her.

  Stephanie picked up her cell phone at a red light and dialed her own home phone number. It rang and rang and rang, and after her voicemail responded, she hung up. She next dialed Karla’s home number, and got no answer. She sighed deeply to herself about everything and nothing, trying to find a way around the thoughts running through her head. After a time she grew tired of the chase, and faced the thoughts head on.

  Stephanie thought about all the relationships she’d ever had with women. Had any of them ever been sexual in nature? Stephanie knew she always thought women were beautiful—their bodies, their smiles, their way of doing things. She then tried to think specifically about Karla, her best friend. Stephanie always thought Karla was the most beautiful woman she knew. She always admired her looks, her style, and the way she did her hair. When they were younger she tried to emulate Karla in many ways.

  As she drove along, Stephanie tried to ask herself the hard questions. Had she ever been sexually attracted to Karla? She thought back to hundreds of sleepovers and Girl Scout camp outs. She thought back to their days in college as roommates, drinking and smoking, pledging, laughing and studying. Karla and Stephanie, always together. Where you saw one, you always saw the other. Inseparable. They shared everything they had. Makeup, clothes and secrets. Stephanie thought back to more intimate moments they had shared. Touches. Kisses. Caresses. Hugs. Those times when they were close physically. Stephanie tried to think about how she felt in those moments. Had she been turned on? She sighed, considering the possibilities all the way to her job.

  Work kept her busy all day, but she did try to reach Karla again, at her own home and then at Karla’s home. At both locations she got the voicemail. Either her best friend was still asleep or had gone home. She tried Karla’s cell phone and got no answer, then sent her an email and got no reply. Karla’s name never lit up on her instant messenger. Stephanie didn’t actually want to talk to Karla yet…she just wanted to know if Karla would still be in her apartment when she got home from work. She wasn’t ready to face her yet. She still wasn’t sure if she had just used her best friend since childhood to make herself feel better about a failed romantic relationship. And if she had, she hated the kind of person that made her.

  *

  When Stephanie got home that evening she threw herself down on her couch, kicked off her sneakers, and stretched out, closing her eyes. Maybe now she could figure out what to do about everything that had happened. With her eyes still closed, she wriggled out of her jeans and tossed them across the room. She raised her body up long enough to
pull her sweater over her head, and tossed it across the room also. Lying there in her underwear, she placed her hand against her forehead. She resumed her train of thought from the morning…thinking about Karla and how she really felt about her. Stephanie often wondered if other women would find it strange if they knew how much pleasure she got from admiring women’s bodies and looking at them—the same way men did perhaps? Stephanie had convinced herself that the way she would look at the women in her ex-boyfriend’s dirty magazines was merely womanly heterosexual appreciation for female beauty—in a non-sexual way of course. Once Stephanie got to thinking about how she always looked at the women in porn movies and not the men, she decided she wasn’t prepared to contemplate the matter any further.