My Life and Other Pleasures
I must admit. I’ve had a great life. I’m 31 years old, I have paternal twins, great parents and a husband that I love to death. I’m also a bestselling author of a book on teen sexuality. The income that I receive from my book allows me to stay at home and raise my twins the way I want. My husband is a successful cardiologist that provides for me and the twins very well.
Following the success of my first book, I decided to write another. I was stumped for a subject, so I started to recall my late teen years.
I was 17 and growing up in a small town. The weekends consisted of hanging out in an empty parking lot with friends or going to the lake until I met Matt. Matt was my age. He was about 5’11” and had curly brown hair. He had a shy disposition as did I, so we got along great. We talked about sex, but wanted to wait until everything was perfect. Having moved here from Salt Lake City six months before, he was adjusting to life in a small town pretty well. My best friend Jennifer warned me about him, but I didn’t want to listen. Matt and his parents attended the local Mormon Church, so he had to be a gentleman, right?
Jennifer was the smart one of the bunch. Also the prettiest, but she never used it to her advantage. We’ve been best friends since 5th grade and could talk to each other about anything. A couple of years before, she had confided in me that she had lost her virginity to one of the local farm boys that she had dated for a while, and that it was the best thing that could have ever happened to her. We were both barely 15, and I was skeptical, so I decided to hold on to mine for a while longer until the right guy came along.
Back to 1999:
Matt, Jennifer, her latest boyfriend Phil and I were at the beach late one Saturday night slowly working on a 12 pack that Jennifer’s boyfriend had brought. “So, what do you have planned for your 18th birthday next month?” Jennifer asked. “What day is it Maddie?” Matt said with a quizzical look on his face. “September 17th and I’m not sure what I’m going to do yet.” I replied. “No shit, that’s my birthday too!!!” Matt told us. “We should do something together.” “We’ll see.” I told him and with that we went back to drinking and wading in the warm summer water.
Matt and I had a pretty normal relationship as teenagers. So I thought. We hung out together whenever we could, go to the movies, made out to a point, but I never let him go too far. I let him play with my tiny breasts under my bra, but when he reached below the waist, I would move his hand away and tell him not yet.
A few days before our birthdays, Matt and I were sitting in the park tossing bread scraps to the ducks. “Matt” I said not looking at him, “Our birthday is in a couple of days and I want to give you something really special.” “What’s that Maddie?” he asked looking at me. Still not looking at him I said, “I want you to be my first.” “First what” he asked playing dumb. “I want to give you my virginity” I said feeling the blush that was rushing to my face. “Maddie you are too cool. I know I never told you this, but I’m a virgin too. I’ve gone to 3rd base and all, but I’ve never had real sex. You just want to park at the lake and do it?” “No I don’t want car sex. “ I told him. “I want some place comfortable. I have an idea, but I’m not sure if it will work out or not.” “I’ll do you right here if it doesn’t” Matt replied with a very happy look on his face. “Shut up Matt” I said with a smile finally looking at him.
On September 17th, my parents woke me up to a special breakfast of my favorite foods, gave me my gift that was a $500 savings bond that they bought the year I was born to help pay for college. I hugged and kissed them both and then headed for school, (so they thought) I met Matt a couple of blocks away and instructed him to drive to my Uncle Robs house. He isn’t really my uncle but he and his ex-wife have been friends with my parents since before I was born.
When we arrived I knocked on the door and Uncle Rob answered with a beer in one hand and a cigarette in the other. “Hi Maddie. What’s up?” He glared at Matt. Uncle Rob didn’t like Matt. Didn’t trust him. He invited us both in and we sat down. “I need a huge favor Uncle Rob.” Uncle Rob was a cool guy, but this request may have been pushing it a bit far. “Me and Matt want to use one of your bedrooms.” He knew what our reason was “Are you kidding me? Your mom will find 15 different ways of killing me.” I told him that I was 18 now and could do what I wanted. He paused for a minute and then walked in to his bedroom. He came back out holding two leashes. “I’m taking the dogs for a walk. I’ll be back in exactly one hour. There are condoms in the night stand. USE THEM!” “Ok Uncle Rob” I told him sheepishly. He then walked out the back door, put the leashes on the dogs and went for a walk.
Matt and I went to the bedroom and undressed each other while we made out. Falling together on the bed we continued to kiss deeply as Matt caressed my small breasts and reached between my legs and clumsily tried to massage my clitoris through my thick bush. He rolled onto his back and reached into the nightstand and retrieved a condom. After pealing it open and pulling the lubed condom out, I reached over and took it from him. I wanted to put it on him myself. His penis wasn’t impressive. About five inches and thin but rock hard. It was nothing like the ones that I’d seen online. I suspected that they were photo shopped and now I knew they were. I rolled the condom onto his penis, first upside down then correctly, and pulled him on top of me. As he continued to grope and kiss me, his penis found my waiting hole. I was quite wet and thought that his penetration would feel fine. The head went in smooth, but when he tried to push in the shaft, my hymen resisted. He then pulled the head out and gave me a hard thrust. My hymen tore and the pain was incredible. I just bit my lip, gripped his shoulders and endured it. He withdrew some and reinserted a couple of times until he was fully inside me and it hurt like hell. “Are you ok?” he asked looking at the headboard more than my face. I just nodded and kept biting my lip. With that, he began pumping in and out of me slowly. After a few seconds I asked him to stop for a minute and he told me that he couldn’t because it felt too good. After about another 30 seconds or so, while the pain where my hymen ripped was still intense, the rest of my pelvic area was starting to feel very good. It hurt so badly, but it felt so good at the same time. I noticed that the tempo of Matt’s thrusts was speeding up and I was feeling like I needed a release of the tension I was feeling real soon. A few seconds later with a groan in my ear and one final hard thrust, I could feel Matt’s penis throbbing rapidly inside me as he filled the end of the condom. He was breathing hard into my ear and went dead weight on me. Once he rolled off, I observed that there were bloody streaks on the condom as well as a tip that seemed loaded with his young sperm. I also observed that the clock on the nightstand said 8:47. When I put the condom on him it was 8:45. Damn. Is this all I get to expect? As he pulled the condom off of his deflated penis he told me that I was the greatest that he’d ever had so far. “What???” I exclaimed. “I thought that you said that this was your first time???” “Sorry Maddie, I lied. You wouldn’t have slept with me if I had told you the truth.” “YOU PRICK” I yelled at him rolling off of the bed. “I STILL MIGHT HAVE YOU ASSHOLE!!!” I stormed out of the bedroom and into the bathroom slamming both doors. On the toilet I wiped myself to see if the bleeding had stopped. There was just a little residual stuff. I heard a door shut and figured that Uncle Rob had come home early. I was in the bathroom completely naked with a wad of toilet paper between my legs and scared to death. Peeking out the door I seen that the bedroom door was wide open, and Uncle Rob had not returned yet. I rushed into the bedroom, put my clothes on and left the house on foot. Matt bailed on me, so I went for a walk to the park to reflect. At about 1 pm, lunch period was over so I went back to school.
Jennifer and I had the last three classes together. When I walked in to English and sat down, she saw the grim look on my face. It hurt but it wasn’t too bad. She sat next to me in every class we had. “How was it” Jennifer asked trying not to laugh. “It hurt so bad,” I told her. I was still feeling the pain as I sat. “We’ll talk after school.” After school I met Jennifer again. Unlike me she had a car and was going to give me a ride home. Matt never showed up back at school. I told her that it hurt so bad, but started to feel so good at the end. Jennifer told me not to give up. “It gets better.” She assured me. “I’ll give you more details later.” I told her.
That night I tried to call Matt but I kept getting sent to voice mail. I seen him from a distance at school, but he avoided me almost to the point of running away from me. Two days later he finally called. “Maddie I have to break up with you. My parents think you’re a bad influence.” He tried to sound sincere, but I could pick up a hint of laughter in his voice. I pressed him for more info, but he just repeated the same line. What a pussy. He dumped me after he broke my cherry just for fun? I can’t believe that he played me for that long and I bought it. One of these days I’ll learn to listen to people that I should trust more than a boy with a plan.
Friday rolled around and Jennifer and I were going about our usual routine at school. Every time I saw Matt he always had a smug look on his face when he looked at me. On the way home, Jennifer asked me to spend the night and I told her that I would have to let my parents know, but that it shouldn’t be a problem. After dinner I let mom and dad know about my plans and they were ok with it. They liked Jennifer and knew that she had always been a good friend to me. Dad asked me about Matt and I fed him a line that we had different interests and had decided to part ways as friends. Dad told me that he was sorry but glad, because he wasn’t sure about him. In retrospect I should have told him the truth and let Matt take the ass kicking he deserved.
Jennifer didn’t live far from me but mom insisted on driving me over. Mom is a bit paranoid and these days I understand why. I reached over, gave her a quick hug, grabbed my bag and walked up to the door. It was only eight o’clock and Jennifer answered the door. I said hi to her parents and we retreated to her bedroom to watch TV and chat. At mid-night after he parents had gone to bed, Jennifer broke out a bottle of cheap wine that she had asked her boyfriend to buy for her and a couple of cheap cups. After a couple of cups, we were both very relaxed and stripped down to switch to our pajamas. Neither of us was inhibited seeing each other naked having gone through puberty together but looking at her body did always make me a little jealous. We were both 5’6” with brown hair, but that’s where it ended. She had perfect C cup breasts while mine were an A cup that all but disappeared when I lay on my back. She had the very curvy butt and hips that men love while mine is a little flat. “So, give me the details about how it was with Matt.” Jennifer said. “It was nothing like I expected.” I told her. “It hurt and was over real quick. Oh yea, the pics of men you showed me online are bullshit. Men don’t have penis’ that big! Matt”s was short and skinny.” “He’s the exception Maddie. There are a lot of guys that are bigger than that. Did he make you come at least?” Jennifer asked. “Go where” I asked confused. “No Maddie. Did he make you have an orgasm?” she said with a smile. “No” I told her. “it was starting to feel really, really good, but then he ejaculated and it was over.” “So he came but you didn’t?” Jennifer asked still grinning. “I guess” I said. I confessed to her that I’d never had an orgasm. I’d been close before, but had never gone over the edge. I wasn’t sure where the edge was, so I never pushed it. We were buzzed by the wine and Jennifer asked me a weird question. “Would you like to have an orgasm now?” “How” I asked curious. ” I’ll give you one Maddie” I looked at her and told her that I wasn’t gay. “It’s not gay if your just experimenting.” Jennifer explained. “Will you stop if it starts to feel weird for me?” I asked. “Of course Maddie.” “What do we have to do?” I said curiously. “I’ll do the work Maddie, you just have to relax.” With that Jennifer started to run her hands through my hair and down my back caressing my skin through the fabric. Seeing that I seemed ok with it, she reached in front and unbuttoned my top. It felt really good so I didn’t resist. She then ran her palms up my belly and too my breasts. They were small but responded to her stimulation quite well. Leaning in she started to kiss and lick my nipples and areoles. I was in heaven at this point. Being very relaxed, I laid down on the bed while Jennifer continued to pleasure my breasts. Working her way down, she stroked and kissed my belly. Once down to my waist, Jennifer gripped my waistband and pulled my bottom down. She didn’t pull it off, just down to expose my bush. Having done that, she started to kiss around it and it had me so hot. Pulling my bottom off the rest of the way, she elevated my left leg and started to kiss and lick her way down my calf and thigh until she reached my bush. “Oh God that feels good Jen” I said. Ignoring me, she buried her mouth in the pubes sucking my outer lips while her hands ran up and down my buttocks gently. Reaching over my leg, she spread the lips and started to work on my inner lips. Oh my God it felt so good. Running her tongue down the lip she circled my vulva slowly and even slid her tongue inside a bit. Seeing that I was quite wet, she slid in one and then two fingers slowly probing in and out why her tongue still worked it’s magic on the lips. The feeling of pleasure and tension in my pelvis was incredible. I needed to release it so bad! As her fingers continued to probe in and out of me, a little faster now, she ran her tongue up the inside of the lips and started to circle and flick my clit. A few seconds of this is all it took. My hips started to shake uncontrollably and an intense feeling of pleasure rocked my entire body starting between my legs and spreading throughout the rest of me quickly. I realize now that it was only a few seconds but I was in paradise for an eternity. So that’s an orgasm I thought to myself. As I started to come down Jennifer slowly withdrew her fingers and gave my mound one final lick right up the middle. I was still quivering as she gave me a quick kiss on the forehead and then lay next to me. When I caught my breath I looked at Jennifer who was slowly circling one of my nipples with her finger. “Thank you, thank you, thank you.” I told her. “That was beyond fantastic.” “You’re welcome, however, now do me.” She said with a sly grin on her face. “I wouldn’t know what to do.” I said feeling a bit worried. “It’s ok Maddie. I’ll walk you through it.” She sat up and unbuttoned her own top and pulled it off tossing it to the floor. “First, kneel over me and softly kiss my neck.” I complied got on all fours and kissed her neck a few times. “No Maddie, do it softly.” I repeated it, this time with less pressure. “That’s great.” She moaned. “Ok, keep doing that and lay at my side. No sweetie, not on top of me. More half on and half off. That’s better.” As I continued to softly kiss her neck, I reached up with my free hand and groped one of her perfect breasts. She told me to caress and not grab and I could understand why. Matt would grope my breasts and it was uncomfortable with my tiny ones. Jennifer’s were quite larger and even I could grip more of them. “Ok, now move down and kiss and lick my nipples the same way you did my neck.” As I moved down, I continued to kiss her chest down the middle while my hand continued to caress her breast. Moving my mouth to the other one, I started to lick and suck it gently. “Oh Maddie you’re doing it great. Now move down and pull my pj bottoms off.” Slipping down I gripped her waistband and tugged with Jennifer raising her hips to help. Seeing her bush up close for the first time surprised me. Unlike mine that was full, hers was neatly trimmed and the hair over her vulva was shaved bare. “Ok Maddie, now use two fingers to spread my lips and let your tongue do the rest.” Following her instructions, I spread her lips and started to lick like a dog. It tasted salty and had a slightly musky scent to it, “No Maddie, lick and flick my clit like I did for you.” Following her instructions I located her clitoris and started to do as she asked. As I licked and sucked it she started to re-act the same as I did. Her hips bucked up into my face as she had her orgasm. I wasn’t sure what was happening, so I just wiped my mouth and moved to lay with her. “You did that great.” Jennifer said pulling me close to her. She hugged me close and kissed me again. “Let’s take a shower.” She suggested. While we were in the shower together she told me that I should trim my pubes. “I wouldn’t know how.” I told her. “I’ll help you with it. Guys don’t like a hairy mess.” She said while rubbing a soapy sponge over my breasts. Once out of the shower, I laid back on the bed and Jennifer sat up between my legs with a pair of scissors. Jennifer trimmed my ample bush down to the point that my crevice was visible but it wasn’t completely bald. I thanked her and her welcome was to lick me to yet another mind blowing orgasm. Moving back up to my side, I gave her a long deep French kiss. We fell asleep next to each other a few minutes later.
In the morning we redressed and went downstairs. Her mother made us a fabulous breakfast. It was great. Eggs, hash and cinnamon toast that tasted so good. Jennifer’s mom wanted to drive me home, but I insisted on walking. The walk was short and the air was cool outside. When I walked in the door, mom asked how my night went. I lied and told her that it was fine. “We watched a couple of videos and went to sleep.” I told her. Going to my room I put on a CD sat up in bed and reflected. In the last two weeks I not only lost my virginity, but had what some would call a lesbian experience. Ok, maybe I might be bi-sexual because I still have a strong attraction to men, yet what I and Jennifer shared was great. Not sure yet.
2012 The present:
I’m still not sure about a subject for my next book, but thinking about my past has stirred up some fresh feelings. I’ll have to tell you more later. I think I’m going to check on the twins, and surprise my husband in his study……..