Sexting for Dummies: You’re So Vain

“If you would have told me a year ago, that I’d ever get seek of seeing that man’s penis, I would have laughed at you. It turns out I saw his cock waaaay too many times today. There were so many pictures of it.  Why were their so many?”

We’ve already covered why sending pictures to the technically challenged is a bad idea.  We’ve discussed why you shouldn’t give a face to your dick/boobs/vagina/ass on the interwebs.

vain2Today’s lesson is just as simple and demonstrates the same colossal lack of common sense as your two prior lessons.  Don’t keep naked pictures of yourself on your phone.  Even if you did manage to keep your face out of the picture (and in the instance I am referencing that wasn’t the case), why would you have roughly twenty photos of yourself naked on your phone.  (The strip tease was really effective, by the way).   It isn’t that difficult to take off your shirt/blouse and/or drop your pants and snap a picture is it? It isn’t necessary to keep a catalog of nudie pics of yourself on your phone unless that’s all you do all day long.

vain4If all you do is send naked pictures of yourself to people then maybe you should have stock pile.  Just put them in a folder and name it my colonoscopy, that way no one will decide that’s the folder they want to snoop through when someone gets their hands on your cellphone.

Aside from trying to secure your career as professional escort/gigolo there is no reason you should ever keep naked pictures of yourself on your phone.  If someone else sees them they will assume you are

A.) Constantly sending out pictures of your junk

or…

B.) Obsessed with yourself or at least certain parts of your anatomy.

vain1(And this is coming from a woman who is completely obsessed with herself.) Either would be entirely unbecoming.  You don’t need to keep naked pictures of yourself and I personally wouldn’t want to.  I would just keep looking at them being all judgey and hypercritical of myself and I work out constantly.  Just t ake the picture, send it and delete it.  Your face shouldn’t be in it so it isn’t like it is a really good or bad picture; it’s just a picture of your dick/boobs/va-jay-jay.

The Big O

For the bulk of my seventeenth year of life I had sex with one person and one person only.  I started sleeping with a guy a barely knew a week before the start of my senior year of high school and continued sleeping with him until just before I graduated.  In the entire span of our “relationship” I only had two orgasms in probably one hundred sexual encounters.

I didn’t know what an orgasm was when I seventeen, well not a female orgasm.  I didn’t know women could have orgasms.  One night after having sex with my high school boyfriend at the house I was babysitting at he asked, “Did you like it?” I said that I did although I wasn’t sure.  The look on face must not have been convincing because he asked, “Well did you cum?”  I was puzzled by the question because boys cum not girls but I guessed that he had either been misinformed or I was missing something.  “Yes,” I responded.  “How many times?”  “Five,” I answered.  I assumed this was a good answer as I could see how proud of himself he was. 

I had absolutely no idea what he was talking about but he stopped asking.  I soon forgot about the question nor did I feel the need to delve any deeper into what the question had meant.  About two months later, in the backseat of a car my boyfriend and I began making out.  He asked if I would fuck him.  I said that I would and my pants were off in a flash.  I remember I was more excited than normal, we had been making out for a while and his hands had been busier than they normally were.  Typically our sexual encounters were rushed and there was little to no foreplay.  This time it lasted a little longer and my kitty had received some heavy petting prior to penetration. 

He took his time with me.  He was much slower and gentler than he had been in the past.  He raised one of my legs so that it was resting on his shoulder and then began thrusting faster and harder.  All at once my body began to shake and felt very warm.  My toes began to tingle and the sensation began creeping up legs.  As it consumed my lower half, my heart began to race and my head began to feel light.  I remember being scared,  I thought I was having a heart attack or a stroke.  At that moment my vaginal muscles began to contract.  I pulled my boyfriend closer to me digging my nails into his back.  I was terrified.  In a moment my body relaxed and my boyfriend pulled out and climaxed on my stomach.

I didn’t mention the incident. My boyfriend didn’t seem to notice that I had nearly had a stroke in the middle of our sexual encounter.  I was too embarrassed by the incident to mention it to my friends, because obviously something was wrong with me.  For the next few days I thought about my “episode” constantly.  After much reflection I decided that what had happened that night did actually feel pretty amazing although I was sure it was not normal.

I decided to try and recreate the conditions on my own and see if the same thing would happen.  One night a week later I lay in bed and brought myself to climax for the first time.  Suddenly it made a little more sense, I wasn’t sure what was happening but I was sure I wanted it to.  I still didn’t mention it to my friends because I didn’t know any seventeen year old girls who admitted to masturbating. Although that night I definitely became a big fan of masturbation. 

Sometime later, after my boyfriend gave me my second coital orgasm I finally learned what was happening to my body.  I was sitting around talking to a group of female friends where one girl was retelling a story of a sexual encounter she had had with some guy at a party.  She said, “I came so hard he had to cover my mouth to keep me from screaming.  My legs were shaking so badly I couldn’t walk.”  A little light bulb lit up above my sexually inexperienced noggin.  I had been having orgasms.

So nearly six months after I had nearly had my first “stroke,” I learned what a female orgasm was. And I surely did love them.  I still love them.  It changed the way I looked at sex and myself.  I realized that I was supposed to enjoy sex and that I could.  It would be a while before I would find a partner who was skilled enough to help achieve climax on a consistent basis but from that moment on it all made more sense.  I have still never come five times in one session but a girl can dream.  I am still looking for the right man for the job.

Playing to My Strengths (My First BJ)

Disclaimer:  Some of my friends may not want to read this as it is a subject dear to my heart and I just don’t know how to write about it without being crude and/or crass.  My aim is not to make anyone uncomfortable so if you feel inclined to proceed, consider yourself warned.

The first time I ever stuck a penis in my mouth I was in my early twenties.  It had taken me a longtime to get comfortable even seeing one because I just thought they were gross to look at, that is until I got a little older and was actually sleeping with partners who were good in bed.  It was then I learned to appreciate, nay, love male genitalia.  By the time I had entered my twenties I no longer minded seeing a guy’s member.  I rather enjoyed fondling and otherwise playing with them but I had become so accustom to telling a man no when oral was requested that I had still never given a man head.

When I was twenty-two, I was dating a guy named Eric, who I worked with.  He is one of the best lovers I have ever had.  He was also very good when it came to oral.  We had been sleeping together for almost a month before he asked me to return the favor.

One night we were sitting in the living room of my house, watching a movie.  We snuggled up together in an oversized chair, my head resting on his shoulder.  His hand rested on the small of my back, slowly began to move under the back of my shirt and down the back of my pants.  I told him to knock it off and watch the movie.  He knew I was only trying to draw my time with him out.  We seldom spent time alone together for any significant amount of time.  He still lived in his mother’s house helping her support his two younger siblings. I shared a house with another single mother.  She had taken our boys out for a night so I could spend time with Eric.

As I sat watching the movie, he shifted so that his hands had more access to the front of me, which had been pressed up against him.  He began kissing my neck, his hands tracing the contours of my body.  He slid his hand under my chin and turned my face toward him.  He pressed his slightly parted lips against mine, caressing my tongue with his own.  “I am trying to watch a movie,” I whined, trying very hard to seem annoyed.  “Fine, watch the movie,” he said smiling at me.  He rose from the chair and squatted down in front of me being careful not to obstruct my view of the television.  “Watch the movie,” he smirked at me as he began to undo my pants.  My eyes locked on his as he pulled my pants off and spread my legs.  “The television is there.” He motioned toward the television with a flick of head. “Watch your movie, Teri,” he whispered as he buried his face between my legs.  I tried to concentrate on the film until his licking and sucking became more rapid and focused.  I slid down in the chair, head back and ran my fingers through his hair.  After a several minutes, he rose from his knees, leaned over the chair kissed me.  I struggled to undo his pants as he kissed slowly and leisurely, tracing my lips with his tongue.  When I managed to get his pants down, he leaned over me further so his penis was inches from my face and whispered, “Your turn.”   I smiled up at him and said, “I don’t do that.”  The truth is I wanted to do it, I had never wanted to so badly.  “Your turn,” he said again softly, sliding his hand behind my head.  I wrapped my hand around the shaft of his penis and allowed him to slide into my mouth.  As I did he let out a soft moan and his head rolled back.  I gently ran my tongue over the head of his dick and began stroking his shaft with my hand.  He leaned over me further still and began to guide my head as he shallowly thrust himself in and out my mouth.   I began sucking gently at the mushroom tip each time he began to withdraw.  When his legs began to tremble he laid down on the carpet to make himself more comfortable.  I kneeled next to him and took him back into my mouth, one hand still stroking his shaft the other resting on his chest.  I took as much of him as I could into my mouth without gagging.  I could feel his heart racing and as it did my movement became more rapid.  His body became rigid.  “I am going to cum,” he mumbled and I took his dick out of my mouth but continued to stroke his penis more firmly and rapidly until he came.

He lay on the carpet quietly for a moment. He pushed himself up off the carpet so he could look at me.  He raised his hand and stroked the side of my face, tracing my mouth with his thumb.  “You are a liar,” he said. “You are so good at that, baby.”  I blushed, leaned over him and kissed him.  And that was that.

From that moment on I fell in love with oral sex.  I absolutely love giving head.  It is my favorite sexual act.  I know women say that a lot without meaning it or because they think they are supposed to like it but I really enjoy doing it.  While I have had doubts about my aptitude in various sexual situations that is one area where I know I excel and I love doing things I am good at.  My oral fixation, something I had been teased for growing up, had finally been put to good use.

I never told Eric he was the first person whose dick I had sucked partially because he wouldn’t have believed me but mostly because he enjoyed it so much when I did.  He insisted at the time that I was better at giving him head than any other woman he had been with.    I think we stayed together for as long as we did because I liked giving him head so much. The truth was I just enjoyed making him feel good and I am a firm believer in playing to your strengths.

“Did You Start Your Period?” (or My First Time)

When I was seventeen all of my friends had already lost their virginity.  I don’t think I knew anyone who was a virgin.  To make matters worse they had all lost their virginities at least a year before I did.  I never really worried about being the only virgin I knew because no one knew I was a virgin, at least most people didn’t.  It was common knowledge that most of the girls I hung out with were sexually active and the assumption was that I was too.   I neither confirmed nor denied this assumption.  By the time I turned seventeen I was more comfortable with acting on my urges with boys, which for me meant making out and dry humping.

I had the same best friend all through high school.  Briana was everything I wasn’t.  She was extrovert, strong and very comfortable with her sexuality.   I envied her confidence and found it easy to hide in her shadow when I was uncomfortable.  Briana was also my biggest instigator.  She never asked me to do anything I didn’t want to but I compared myself to her constantly as the standard of the” All American” teenager.  She had hit every milestone I thought I had missed and I created a timeline of milestones for myself based largely on Briana’s accomplishments.

One Saturday in late September, Bri spent the weekend at my house.  We planned on going to a party that Saturday and sat in my room devising a plan to sneak out of the house so we could go.  Sneaking out of my house was no small feat.  We had done it before but we always found it helped to plan it out in advance.  As the sun was setting we sat up in my room and came up with a way to get out of the house.

I lived in a federally subsidized townhouse on the edge of the desert town where I grew up.  Once Bri and I were able to get outside everything would be easy.  Getting out of the house was another story entirely.  My mother had had chronic COPD for most of my youth.  Because we lived in a two story apartment and my mother was on oxygen twenty four hours a day, she slept downstairs on the couch.  Because of her breathing difficulties my mother was also a very light sleeper.

Once we had come up with a plan, we just had to execute it and wait for our ride.  Phase one of the plan required that I sneak downstairs and unlock the front door of our house without being detected by my mother.  I crept downstairs slouched over so that my mother couldn’t see me.  When I reached the bottom of the stairs I sat down and stared at the front door for a moment, listening for any indication that my mom was up and moving around.  “Teri?” my mother asked.  “Fuck!” I mumbled under my breath. “Yes,” I responded.  “Why aren’t you in bed?  It is nearly eleven.” my mother inquired.  I looked up at Bri standing at the top of the stairs.  She rolled her eyes as I frantically tried to think of a lie.  “I am using the bathroom.  Bri is in the one upstairs.” I said.  “Well use it and get to bed.” my mother said.  I hurried into the bathroom which sat at a ninety degree angle from the front door.  I went into the bathroom and waited a moment.  I listened for my mother but didn’t hear her get up.  I slowly opened the door and stepped quietly back into the hall.  As I did, I quietly put my hand on the knob of the front door and unlocked it. Again I listened for any indication my mother had heard me.  She was still on the couch.  I stepped back into the bathroom flushed the toilet and darted back up the stairs.

Getting ready quickly and quietly was Phase two.  Briana put on a pair of jeans and a black t-shirt.  She was beautiful.  I wore white leggings and tuxedo shirt.  I looked like I was still in junior high.  Phase three required us to do something I always hated doing but had done many times.  We removed the screen from my second story bedroom window and made our way out onto the windows ledge.  The two foot wide ledge actually ran along the entire front of the duplex building I lived in.  As we quietly made our way out onto the ledge our ride pulled up and was directed by Bri to park in the school parking lot across the street.  Briana sat on the ledge of the building, legs dangling and indicated for our escort to come help.  When he arrived in the yard, Bri fearlessly jumped off the edge and he did his best to lessen the impact.  I sat down and scooted to edge as Bri had.  When I looked down at the boy and Briana standing in the yard I got dizzy.  Bri said, “Jump damn it!” in annoyed voice I heard anytime she was feeling anxious.  “He’ll catch you.” she said coaxing me to jump.  I slide down further so that I was hanging off the ledge.  I felt hands on both of my legs and I let go.

We made our way to the car and drove off to the middle of the desert.  When we got to the kegger it seemed as though things were wrapping up.  The keg was nearly empty so Bri and I camped out next to it drinking party cup after party cup of beer to ensure we would be drunk before the keg ran out.  After about five cups of beer each, we were drunk and the keg was empty.  Briana wandered off into the warm desert night to socialize and I found a huge rock nearby, sat down against it and stared up at the beautiful, starry night sky.  I didn’t know many people at the party and I was more than content to enjoy my buzz alone.

Within the next twenty minutes word had spread that the keg was empty and people began to pile into cars to leave.  Briana found me sitting alone and informed me that we were leaving and headed to another party.  She pulled me up to my feet and we climbed back into the car we had arrived in.  Two new boys were coming with us.  Briana sat up front and I sat in the back with the guys.  I had never seen the boy sitting next to me.  He had brown hair and dark eyes. He was cute and I was drunk.  We stared at each other for along moment and he scooted closer to me pressing his leg against mine.  As I leaned forward to ask Briana where we were going I put my hand on the boy’s thigh.  Without a reaction he took my hand moved it to his groin.  She informed me that we were going to an empty house back in town.  Satisfied with answer and a place I could make out with the cute guy sitting next to me I leaned back in my seat.  His tongue was in my mouth before I could even get comfortable.

By the time we reached our destination, he was already grinding himself into my hip in the backseat.  John, the boy sitting next to him had voiced his opinion about the awkwardness of our current situation very loudly several times.  Everyone laughed but we proceeded making no attempt to make him comfortable.  Our driver informed us that he would be back in an hour to pick us up if we planned on getting a ride home.  We agreed we would be ready in an hour.  The boys lead us to an open window on the side of the house and we climbed through one by one.  John, who had been sharing the backseat with us tapped my make out partner on the shoulder and pointed out the where the bedrooms were.  He promptly grabbed my hand and led me to the closest door.

Once inside he shut the door behind us and pulled me to him and began unbuttoning my shirt.  As he did I realized I still didn’t know the boy’s name.   “I don’t remember your name,” I said.  “It’s Mike,” he said concentrating on undoing my shirt.  “I’m Teri.” I said.  As he guided me to the floor he said, “I know.”  I was lying on my back in the empty room and realized for the first time that he had taken my shirt off.  I had never let anyone even think about taking my clothes off.  He lay down next to me and began pulling my pants down around my hips.  I began to sober up rather quickly.  What was I doing?  Was I going to have sex with a kid whose name I had found out only moments ago?  I took his hands and moved them to my chest.  He smiled content for the moment with my suggested alternative.  It gave me a moment to think.

I was certain that this boy did not go to my school1 and if I let him have sex with me I would lose my virginity and no one would have to know.  I could just do it and would no longer be embarrassed answering when someone asked me if I had had sex.  I was seventeen and the only virgin I knew.  I resigned myself to the fact that it was time and in my half-drunk state my rationale seemed pretty sound.  I wasn’t going to be a virgin after tonight.

My would-be lover grew tired of playing with my breasts and slid his hand down my stomach and into pants.  I was on fire.  I was experiencing a ton of first-time sensations in a matter of alcohol hazed moments.  My hand found his wrist in the dark and I held it gently as he massaged me under my pants.  My hips began to match the rhythm of his moving fingers.  As his fingers searched vagina he began sliding one of his fingers inside me.  My grip tightened on his wrist in an attempt to stop him. He pulled his hand out of my pants ran it up my side.  I was trembling noticeably.  “Are you okay?”  he asked sliding between my legs and pressing himself into my me.  “I am fine,” I answered.  And he kissed me.  As he rhythmically pressed himself up against me my body started matching his thrusts.  While I was trying to determine whether or not I wanted to have sex my body decided I was absolutely ready.

Every part of my vagina was throbbing and screaming for more contact.  He pushed himself up off of me just enough that he could look in my eyes and asked, “Can I fuck you?”  After a moment of shock at his crude request I nodded.2  He slid my pants off and removed his as well.  I was suddenly embarrassed.  I couldn’t look at him. I had never seen an erection before.

He again situated himself between my legs rubbing my clitoris with his penis.  When the anticipation had almost become unbearable he slid the head of his penis inside of me and removed it.  He did this several times then leaned over me and pushed.  I let out a little scream and felt an awful stabbing sensation that made me lightheaded.  Without even realizing it I was scooting out from underneath him.  I put my hands on his chest and pushed him up away from me.  He stopped for a moment and I scooted back so I was lying with the back of my head resting against the wall, my chest rising and falling as though I had just finished a marathon and tears welling up in my eyes.  He couldn’t see me very well but he could feel the tension in my body.

“Am I hurting you?” he asked.  I nodded.  He noted I was tight and asked if I wanted him to go slower.  What I really wanted was to stop or to tell him that this was my first time but I was embarrassed.  I nodded again and he took my hips and pulled me back underneath him.  He slid inside me once again moving much slower than before.  He buried his face in my neck. I bit down on my lip to keep from crying out again.  I lay frozen underneath him.  After a few minutes he began moving more quickly again and I let out little yelps of pain which seemed to make him move even more frantically.  He quickly withdrew and came on my stomach. He lay down beside me.  With his chest pressed against my breast I could feel his heart racing much like my own.  He traced the contours of my stomach with his fingers and kissed my neck.  My vagina was throbbing.  My legs were shaking so badly I would have fallen if I would have tried to stand.  He pushed himself up over me again and kissed me.  “That was fun,” he said. I smiled at him.  He sat up and looked around for his pants.  When he found them he stood up, pulled them on and left me in the room, alone in the dark.

I lay there for several minutes trying not to cry from the discomfort I felt between my legs.  I finally sat up and fumbled around for my pants.  When I was dressed, I opened the door and found everyone in the living room.  When I sat down next to Briana I noticed she had a black eye.  She said that she had been wrestling with John and caught an elbow.  We all sat around and talked until our ride showed up.  On the way home we constructed a story that would explain why Briana had a black eye, an injury she had not had when we went to bed.3  It wouldn’t be the only story we would have to come up with.

When we got to my house we crept back upstairs, locking the front door behind us.  When we reached my room Bri flipped on the light.  “Oh my God Teri!” she exclaimed.  “Did you start your period?” she tried to suppress her amusement.  I looked down at my white pants.  The crotch and inner thighs were covered in blood.  As I looked at the mess tears again began to build up in my eyes. “No,” I answered with a shaky voice.  “Did you lose your virginity?” she asked with much more concern in her voice now.  I nodded and began to weep.  She hugged me and promised not to tell anyone.  “We’ll just tell your mom you started your period in the middle of the night,” she said.  I went into the bathroom and took a shower to clean up.  When I was finished I tried to clean the pants to no avail.  I left them crumpled up on the floor.

I lay in bed that night not knowing what to feel.  Was I supposed to like the boy I had slept with?3  I wasn’t sure if what had happened had meant anything. I wasn’t sure I wanted it to happen again.  I hadn’t wanted to be a virgin and now I wasn’t but it hadn’t exactly gone the way I imagined it.

Briana kept her promise and never told anyone about how I lost my virginity.  It didn’t matter because a few days later John, who had “wrestled” with Bri, cut class and returned to the house.  He went into the room where I had had sex for the first time and saw the blood.  I became known as the girl who had sex while she was on her period and soiled the hook up house forever.

1 Turns out he did in fact go to my school.

2 I don’t know what I expected him to say.  I just guess I assumed the fact that it had gone that far was an indication that I wanted to proceed.  It never occurred to me that he would ask.  They didn’t ask in the movies.  And I was not used to people using the word “fuck” to me in that context which is just hilarious now.

3 We told my mother that we were throwing stuffed animals at each other and one had hit Briana in the eye.

4 I did actually spend most of my senior year dating Mike off and on. Just after we broke up for the last time, in early June, I discovered I was pregnant.

My First …

Since everyone seems far more interested in my blog when I am disclosing personal and often embarrassing information about my sexual history and I have had requests to be more explicit in the retelling of said very personal, often embarrassing stories I am going to write about my “firsts” for the next week or so.  My intention is to write about as many of them as I can think of and post them every other night. 

I recently had a conversation with a friend about whether or not I was concerned about future employers reading my blog.  I like talking about my life and I like that most of the time the things I share are amusing albeit inappropriate for some audiences.  It isn’t like I am looking for job working with children.* I produce video and write freelance articles, articles that are almost always about dating and bad relationships and my blog really helps that aspect of my professional career far more than it damages it.  If anything I am more afraid of the impact it might have on my dating life once I actually get to the point of wanting a relationship.

So in the interest of trying to write something that is a little further out of my comfort zone and spending a couple of weeks writing about two of my favorite things, sex and myself, I am going to share some of my personal experiences in greater detail.  And if there are any requests leave a comment and I’ll share that first experience too.

* Fun fact: I did produce and direct an award winning children’s series for two years.

All Guys Have One

Seems the theme of last week’s articles and blogs were pretty uniform. It was all big dicks and anal sex. I don’t really have anything to say about anal sex but I am willing to throw my two cents in about the well-endowed. It all started with an article Why I Hate My Giant Dong written by Charles Allen for The Good Men Project.  It was an article in which he documented the mixed blessings of having a massive member.  Within hours of the article’s posting every female magazine on the web had commented.

I give less than a shit how big your dick is.  I just like penises.  I really do.  For a girl who was terrified of male genitalia until she was in her twenties I feel like I really missed out on what could have been some awesome times, had I actually been ready to have sex. 

As a young woman I had no desire to see a man’s penis, not even during sex.  I was all about the penetration.  Get those pants off and put your p in my v.  Needless to say I never performed fellatio. I had no desire to look at any dude’s member.  They were freaky looking and I was truly a prude.  It took considerable coaxing to get me to give a boy a hand job.  Now I have no such reservations.

The size of a man’s penis has no bearing on whether or not I would sleep with him.  Maybe that is because I have never had sex with anyone I thought had a tragically small penis. I am typically attracted to or turned on by what said penis is attached to and I have never not slept with someone I wanted to see naked just because they didn’t live up to my expectation’s in the size department.  If he is larger than most, good for him (and maybe me.) 

I think skill is far more important than size and I don’t remember any given instance where I thought the sex was better just based on a man’s size.  If I am sleeping with someone who is concerning himself with whether or not the experience is pleasurable for me, that is enough.  Don’t be selfish. Act like you give a shit that there is someone else in the room who would like to have an orgasm.  Decent size penis is nice.  A giant, walking, talking prick is not.

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