Lipstick and Other Stories Read online

  We covered a lot of territory over the next few weeks. We talked about erections. The different types of erections. The I haven’t had any in a while super hard on, the glad to see you/you look hot erection, the response to extremely well executed stimulation erection, the second round erection, the semi hard-on, the I’m a little pooped but damn that feels good erection, and even the mini erection that men sometimes got when given blow jobs after sex. I explained the origin and psychology behind all of them, explaining which stimulation techniques worked best for which kind of hard on. I talked about the reality that while attractive women did sexually stimulate men, a secure woman in a loving relationship with a man that demonstrated his devotion to her could use this to her advantage. “Don’t spend so much time worrying where he gets his appetite,” I would say, “as long as he always eats at home.”

  We then talked about the importance of not excluding testicles from blowjobs. I cautioned the women to not forget to show the balls some attention while they were down there. How much attention would be necessary might vary from man to man, but I wanted to make sure they didn’t make that oversight. I also reminded them of the “sweet spot” behind a man’s testicles before you reached his anus. I reminded them to occasionally give a blowjob after sex because penises were highly sensitive after ejaculation and many men enjoyed the heightened sensation.

  The final lesson before we delved into specific approaches and techniques was about the basic elements of a good blowjob. I always taught my classes the E.R.E.C.T. approach…entry (into the mouth), response (from the man), escalation (of the blow job), culmination (whether it is that the man cums or sex begins) and tranquility (which should be the end result). I taught my students to keep their lips moist; to ease the penis into the mouth through slightly parted lips, attending only to the head first with the lips and tongue. I taught them the slow circular motions men loved, and the gentle sucking that most heads craved. I taught them to slowly ease the rest in, bit by bit, while applying suction and rubbing their moistened lips across the shaft. I taught them to continue tonguing the head of the penis as they took more of it into their mouths. I taught them to use suction to apply pressure, and to move the penis in and out of their mouths rhythmically, applying the suction and moisture the same way. I taught them to gauge their approach by the man’s response. To pay attention to whether he moaned, or squirmed, or tried to push more of himself into her mouth. I taught them to also make themselves familiar with how much pressure and tension their man enjoyed. After all, some men liked it harder than others, slower than others, or quicker than others. I taught them to carefully remove their lips from their teeth guarding duties when they sucked a man’s dick, and to slide it in and out of their mouths with the suction helping to drive them along. I taught them to rub the insides of their mouths against the shaft. I taught them that it was their job to set the pace when giving head. I compared them to drummers in a band, keeping time for everyone else. I thought them about the a slow steady buildup that should level off and plateau two or three times, during which time they should just take the time to allow their man to just relax…just fully enjoy the blow job. When it came time to talk about the myths and realities of deep-throating, I taught them about controlling their gag reflexes so they could take as much as possible into their mouths, and we did exercises that helped promote gag reflex control. For those willing to swallow, we talked about how to prepare for it, how to take the sperm into the mouth without gagging, and how to swallow without removing the penis from the mouth.

  They then began practicing. On bananas. On cucumbers. On simulated penises with different flavors that I provided. On dildos. We alternated sizes so that the ladies could learn to adjust to different lengths, widths and girths. I would give them a situation and ask them to perform the blowjob appropriate for the task. For example, you haven’t seen your man for three months. He’s been faithful to you and hasn’t had any sexual contact with any other person. He comes to see you. What kind of blowjob do you give him? Most importantly, they practiced on live dicks. The feedback was always invaluable. Sometimes it would become the topic for a class. For example, one man told his wife that he liked her to stroke him with her hand as she moved her mouth up and down his penis—a sort of hand job/blow job combo. We spent a whole class on the topic of hand placement during blow jobs—on stroking a man’s shaft while helping it into and out of the mouth, on rubbing, caressing and massaging his balls, on using your hands on his hips to pull him more deeply into your mouth and to pull him out, and so on. It was a good topic to cover, and something I added to my lesson plan for future classes.

  The course ran for 8 weeks, and met twice a week for 45 minutes. In addition to our class discussions, we watched movies—everything from R rated teenagers-getting-laid flicks to a scene or two from some actual X-rated films. We read erotic literature and poetry. We talked about setting the mood for sex in general, and how blowjobs played into the overall scheme of good sex. We talked about the symbolic submissiveness of the blowjob and how many women took issue with it for that reason. We talked about the cheapening of the act. I told them that they had to define their sexuality for themselves, and could not allow pop culture or society to do that for them. After they defined their sexuality for themselves, loved themselves for it and became comfortable with themselves, they next had to seek out partners who would love their sexual selves too. We talked about “oral aids”—tongue vibrators, champagne, flavored oils, cough drops, and spicy mints—to enhance sensations. My students traveled very far in their knowledge of sex in a short period of time. They never failed to make me proud.

  I truly enjoyed my work. I considered it a calling of sorts. I never tired of hearing from my former students. They would always thank me for giving them the skill to please their mate and the freedom to explore other things. I was not exactly a cold, jaded professor, but my job was to give instruction and constructive criticism. To do that I often had to distance myself from the pleasure of the experience. My joy in blowjobs came through my teaching ladies to execute them well and from seeing my students’ eyes light up when they finally got it. Even though many beautiful, sexy women passed through my classes, I always maintained my professionalism in dealing with them. So yes, I enjoyed my teaching, even though I gave up some of my personal intimate enjoyment of receiving oral sex to do it—not that I minded…well, not much.

  Giving the final exam was always my favorite part of the class. I gave the women the option of videotaping themselves giving a man a blowjob, or giving the partner of their choice a blowjob in front of me. The woman was required to give a full service blowjob (swallowing was always optional and was considered extra credit). I always talked to the man afterwards to get his feedback after the blowjob was done and gave the woman a grade based on enthusiasm, seduction, technique and execution. The grade given on the final exam was 50% of their final grade. Every now and then I had a student who wanted to give me a blowjob, claiming they had no one else in their lives. I always turned these students down, no matter how much I wanted to assist them —until Ruth appeared in my office.

  Ruth was one of my better students. She was a young woman, about 22 years old, caramel colored, and wore her hair in cornrows down to her shoulders. She was an athletically built girl, thick but not at all fat, with faintly muscled legs and arms. She wasn’t exactly shy in class—she would occasionally ask questions and initiate discussions, but she was by no means the most talkative. I most remember her incredibly dark eyes—such a dark brown they were almost black. She had the most perfect lips I had ever seen on a woman. They were pink and perfectly formed…full, curved at just the right places and pointed at just the right places. They were absolutely symmetrical. Often when she spoke to me I had to ask her to repeat what she had said because I hadn’t been listening. I was gazing at her lips. I secretly hoped she would be extremely successful in my class because she could provide a man with incredible visuals with her eyes and her incredible lips. I always
emphasized the importance of visuals to a man—that he wanted to see a woman’s lips slide up and down on him and to see the woman’s ass pointed heavenward as she took care of him.

  *

  That last day of the course was a blistering hot day in June. Class had ended. I was in my office, entering grades into my computer. Ruth knocked on my partially opened door. She was dressed in a very short miniskirt and a halter-top, both white. She was carrying a folder. I looked up, and seeing her, smiled. “Ruth. What can I do for you?”

  Smiling back, she shut the door. “Mr. Holly,” she began. She removed a tube of Chapstick from her skirt pocket. She began applying it to her lips.

  I immediately got hard.

  “Mr. Holly, I need to complete my final with you. Now, I know you have rules about this sort of thing. I need you to make an exception, just once. For me. You won’t be disappointed. To show you how serious I am…” She put down the folder in front of me and said, “take a look.”

  Inside the folder was a detailed four-page confidentiality agreement, basically ensuring that she would not reveal anything about this encounter to anyone for any reason, that I would grade her fairly, that she would not in any way dispute the grade she got. Neither of us would pursue a relationship based on this one-time encounter. It stated that any information I received from this encounter would be used for the sole purposes of assigning a final grade. It was ironclad. No student had ever approached me in this manner. I had to admit it was very tempting. I felt things stir inside me, my professional demeanor clashing with my very manhood. I could not withstand the pressure bearing down on me—the weight of her sensuality, of the passion I could see in her eyes and her lips. My heart began to beat faster and faster. I was actually excited about the prospect of Ruth putting her mouth on me

  Almost instinctively, I picked up a pen. I signed by the three x’s she had highlighted in the document. She leaned over my shoulder and signed on the x’s below mine. I could smell her. She smelled so good I could actually taste it. I looked down her halter, sighing deeply and inhaling the scent of her.

  She smiled as she stood up. Going over to the copier, she made a copy and gave it to me. I put it on my desk.

  “Now what,” I asked.

  She went to my office door and locked it. Reaching behind her neck, she untied her halter-top and it fell, revealing her full breasts, riding high, topped with fudge colored nipples. I made a mental note to give her points for providing good visuals.

  I was still sitting at my desk, when she knelt down reverently in front of me, as if she were about to pray. She smiled, and my penis grew harder as I admired her lips. She grabbed the legs of my wheeled chair and pulled it closer to her. She unzipped me and I raised my hips upward to allow her to pull my pants down to my ankles. She then knelt before me again as my rock hard dick pointed at her chest. Then she moved closer to my dick, and nestled it right in her cleavage, with her hard nipples pointed into my crotch. I looked down, admiring the contact of my dark skin against her lighter colored flesh. She touched the sides of her breasts with her hands, squeezing her titties closer together, rubbing my dick between them. Her skin was so supple. As she continued to rub my dick between her breasts, she began to point the tip of it upwards, towards her mouth, towards those lips. She looked up and smiled at me one last time before bowing her head and gently kissing the top of my dick.

  I felt her tongue quickly flick out and touch the very tip of the head, rubbing against it for just a second or two before retreating back into her mouth. Then she kissed it again, and again. She licked her lips, licked the tip of me, and kissed it again. All the while she moved me between her incredible breasts while I worked hard to suppress a moan.

  Just as I had instructed her, she tended to my head royally. She rolled her tongue over it as if it was all she had ever wanted to do in life. She drew the head into the edges of her mouth firmly and gently, sucking on the head and applying moisture. She continued to apply her tongue to the very tip of my dick as she sucked. No teeth. I was amazed. She had truly been paying attention, and she was clearly naturally gifted in this arena as well.

  Then she began to ease more of me into her mouth. She kept her teeth away from me, and continued to lick my head and began to slide me inside her mouth, caressing my penis within the confines of her mouth. It was hot and wet, and so fucking good. I sharply drew my breath in as she sucked me in, deeper, deeper, and oh my, deeper still, until my entire shaft filled her mouth. She continued to suck, drawing me in deeper still, sliding me in and out of her mouth, just an inch or so, then back into her throat, holding me, releasing me by sliding me back out, and then back in, and out and in. I was fucking those awesome pink lips that I had never really seen until this day, and she let me, just let me feel it all, all of her mouth on it, in and out at a steady pace at first, moving faster, then slowing. I stroked her mouth for all I was worth, grinding my hips in the air and trying to figure out how I could regain my composure and give this incredibly hot young woman a fair grade. She was milking my dick with her mouth and causing me to forget all my years of highly professional conduct, in spite of the subject matter I taught. Then she deep-throated me, and I felt the head of my cock touch the back of her throat, with my shaft completely engulfed in her cavernous mouth and her lips at the base of my dick. She held me for a moment in her mouth, just like that…and then…began to slide me back and forth in her mouth, still keeping all of my dick in her mouth. Just tiny little movements…little ripples…my dick just vibrating in and out her mouth…little pulses…inoutinoutinout…I didn’t mean to but I grabbed the back of her head. She grabbed my hands and held my hands to the back of her head. She wanted me to hold her head and I did. I held on to her head, easing her head back and moving it forward to engulf me again just when I wanted to, in complete control. She was totally at my mercy, and I fucking loved it, and she did too. She did not turn away or refuse me in any way, just let me move myself in and out of her mouth at will. I held her and pushed my entire dick in her mouth, and she took every inch. This girl was getting an A plus, no doubt. The next thing I knew, I came. In her mouth. Between her gorgeous lips. She swallowed and continued to suck me as I spurted and groaned loudly. She held me after I had come in her mouth, sucking me soft and slow. Finished, she released me, stood, tied up her halter, took the folder and left, leaving my copy of the confidentiality agreement on my desk.

  “Brava,” I thought to myself, “A plus and then some.”

  Pussywhipped

  To Charles

  I sat outside the psychiatrist’s office. The waiting area was fairly empty. I shared the room with one other harmless looking woman wearing a rather low cut black dress. Quite naturally, my eyes found themselves drawn to her ample cleavage. I gazed at her smooth round breasts nestled inside the thin fabric, looking like two lips tightly pressed together. While my eyes sent the messages to my brain that she was an attractive, sexy woman, I found that my penis was not at all interested. Reggie, as I called my penis, perked up for only a passing moment as my eyes took her in. Then, quick as a flash, he went back into sleep mode, saying, “Linda’s look better. They’re bigger too.”

  Linda. The very reason why I was here.

  “Mr. Andrews,” the nurse’s pleasant voice called. “You’re next.”

  I stood up, towering over the petite lady. Smiling, I followed her through a door, turned a corner and went through another door. Walking a respectful distance behind her, I checked out her hips and ass. Not bad at all I thought, and quick as a flash Reggie chimed in, “Damn Linda’s ass looked good when I’d be hitting it from the back.” Aaaarrrrgggghhhh!!!

  Finally, we reached a door with a plaque that read “Dr. Richard Hendricks”. The nurse knocked on the door and opened it saying, “Dr. Hendricks, Mr. Andrews is here for you.” I opened the door wider. “Afternoon, Dr. Richard,” I said, smiling.

  “Good afternoon, Mr. Andrews,” he responded. We shook hands. “Come right on in and we’ll get start
ed.”

  I walked into his office and sat in one of the comfortable chairs. The nurse shut the door firmly behind her as she departed.

  “It’s good to see you again,” Dr. Richard began. I had been a patient of Dr. Richard’s on and off for a while now. I had initially gone to see him when I found myself unable to deal with my mother’s death after a long bout with cancer about three years ago. At first, I had been embarrassed to consult with him about my issues—it wasn’t the manly thing to do to me. I had to admit, however, that Dr. Richard had been a good therapist, a good counselor, and at times, even a good friend in a professional shrink kind of way. He’d helped me a lot. I hoped he’d help me this time.

  “It’s good to see you,” I replied. “It’s been awhile.”

  “Yes it has,” he responded. “But in my line of work, no news is usually good news. What’s going on? How is that lady of yours by the way…Linda is her name, right?”

  Now he’s good, I thought to myself. In less than two minutes, he had gotten to the heart of my problem.

  “Actually doc…she’s the reason why I’m here. We broke up.”

  Dr. Richard was silent a moment. “Really,” he asked in his professional ‘doctor’ voice. We were no longer just making small talk. Now I was having therapy. Linda had officially driven me to consult my shrink.

  “Yeah,” I said. Knowing that his next question would be, “Do you want to talk about it?” I figured I’d jump right in.

  “Linda and I broke up. Well…she broke up with me. I knew she wanted to take our relationship further. She hadn’t said anything about marriage but…I knew it was coming. I’m still dealing with being divorced. I wasn’t ready. I’m not ready. I mean, I know we’ve been together a while now. For the most part, it’s been good but I kind of got distant on her. Stopped returning calls, fading to black. You know. She finally told me to get lost. I didn’t want to deal with it anymore. It was okay while it was fun, then it started to get…serious.”