If you’d told me in high school that my adult life would be like this I would’ve called you crazy. After all, I seemed to have the whole world in my hands when I graduated with a full engineering scholarship to the college of my dreams. I devoted so much of my time and energy to studying that I missed out on having a social life and never gave a second thought to my appearance. To me, those things didn’t matter at the time because I was certain that once I graduated from college and landed my dream job the rest would just fall into place. I took for granted that good sex, a busy social life and the style and beauty that alluded me throughout school would come naturally to me as an adult, and all because I’d worked so hard toward my dream of being a successful career woman. What was I thinking?! At thirty-five I found myself wearing the same frumpy t-shirt and jean wardrobe I’d donned all through high school, as timid as ever, and with a series of failed relationships under my belt.

Seth was the last guy to really break my heart. I was completely sideswiped when I received a text at work one day from the man I’d hoped to marry: “Sorry, Bev, can’t do this anymore. I’ve met someone else. I’ll be gone by the time you get home.” Given my history I should’ve seen it coming. Seth and I stopped having sex for at least two months leading up to his departure. It could’ve been even longer, I’m not sure. Sex just wasn’t something I was that into. It’s not that I didn’t want to be. I just never felt desirable, and I lacked the confidence to really let go of myself enough to enjoy sex. For me, sex felt like a performance that I had to maintain until whichever guy I was with at the time finished pumping. Sure, I fantasized all the time about sexual fulfillment – about having the courage to be on top and let my partner see my heavy breasts and curvy figure in all their glory, about feeling comfortable masturbating in front of a lover, about spreading my legs for a man and looking him in the eyes as he licks my pussy, about knowing how to make a man moan uncontrollably while I suck the cum out of his cock, about riding a dick with no inhibition, about experiencing mind-blowing orgasms in the company of someone other than my vibrator . . .

Like I said, I had plenty of fantasies. But I didn’t have the guts to live them out. Basically I was a one trick pony in the bedroom: missionary position and a well-rehearsed script of moans, sighs, and stereotypical sex talk – whatever it took to make him cum and get him off me. It was no kind of sex life for a woman in her prime, and apparently no kind of sex life if I wanted to keep a man. Seth was just the latest of a string of boyfriends, all who complained that I just didn’t do it for them in the bedroom. When he left me a little over a year ago I went into a black hole. I’d counted on marrying Seth and finally being able to put my fear of being abandoned to rest. Not that Seth ever even hinted at wanting to marry me. As a matter of fact, he avoided that topic altogether for the entire three years that we lived together. Truth be told, I knew that Seth needed me, so I assumed he’d want to seal the deal. He couldn’t hold a steady job for the life of him. When we got together, it was he who moved into my house and he who borrowed money from me and he who needed me to make his car payments when he fell short on cash. As shitty as that situation sounds, I’d accepted it as my fate and my whole world came crashing down when Seth left. I couldn’t eat or sleep. I sometimes slept in the clothes I’d worn to work and then wore them to work again the next day. That’s when coworkers started showing concern, looking at me with eyes of pity and asking if I was okay. For the most part, I didn’t feel comfortable opening up to any of them. Out of insecurity, because I didn’t want people knowing how lonely I was, I’d made a big production out of being engaged to Seth, even going as far as to wear a fake engagement ring to work. I didn’t want to face the humiliation of fessing up so I kept a safe distance from everyone in the office.

Monica was different. I’d been curious about her ever since she started heading the marketing division two years prior, mostly because she kept to herself and there were always rumors floating around about her fucking this coworker or that. Monica was tall and full-figured, and dressed with confidence in low-cut, form-fitting dresses. Wavy brown hair and bright red lips gave her the appearance of a nineteen forties pinup. She was sexy and beautiful to me – the kind of woman I wanted to be. When she stopped by my desk on one particularly bad day to invite me to lunch, I shyly accepted.

Monica wasted no time telling me that she knew exactly what I was going through. She didn’t even have to ask. I watched in disbelief as, over soup and sandwiches, she tearfully relayed her own similar experience, citing it as the reason she moved across the state and took her job at our firm. It was hard to imagine Monica as the sexually frustrated, timid pushover she’d been before. When I asked her how she overcame her own crisis, she told me she’d made a Fucket List.

What’s a Fucket List? It’s a checklist of things to accomplish related to one certain goal: learning how to really fuck. For a woman who has been sexually repressed for most of her life, learning how to fuck is not a simple task. It requires self-esteem, courage, knowledge and experience. I made a pact that day over lunch, both with Monica and with myself, that I’d put some serious thought into my own Fucket List and that I wouldn’t stop until I’d checked off each and every task. Finally believing in the possibility of my own sexual freedom, and with Monica for moral support, I approached my list with more excitement than I had my high school physics homework. Here’s what I came up with:

My Fucket List

1. Reinvent my image: clothing, makeup, hair . . . tattoos(?)

2. Get comfortable with showing off my body.

3. Learn how to deep-throat a cock.

4. Bring a stranger (or two, or three) home for a one night stand.

5. Kiss (fuck?) a woman.

6. Masturbate to orgasm in front of a man.

7. Sit on top and ride a dick like there’s no tomorrow.

8. Have a threesome with a couple.

Monica squealed with delight when I revealed my list to her the next week over lunch. By that time we were eating lunch together every day and quickly becoming best friends. We agreed to meet that weekend at the mall for my makeover, which she would oversee. She said she had big plans for me. And she was right.

Our shopping excursion was the most fun I’d ever had while trying on clothes. Monica had great taste and knew of the best stores for my curvy figure. She also hooked me up with her personal hairstylist at the ritzy salon next to the mall, where I had my hair, nails and makeup done. I hardly recognized myself when they did the reveal. I thought for a second it could’ve been Anna Nicole Smith staring back at me from the mirror. I looked so hot I wanted to fuck me!

We went out for dinner and drinks afterward to celebrate and when I was good and tipsy, Monica told me she had one last surprise in store for me. My first tattoo was Monica’s treat: a butterfly on my shoulder, symbolic of my transformation. I never would’ve had the nerve to go the tattoo shop alone, so I was so glad to have Monica there to hold my hand. It’s a night I’ll never forget, and for more reasons than the tattoo . . .

It was nearly eleven o’clock at night by the time Monica’s convertible beamer pulled into my driveway. She eagerly accepted when I invited her in for coffee. The whole day and night had been a whirlwind and we both wanted to sober up a little. I noticed as we sipped from our mugs that Monica’s tone had changed. She seemed to be shying away from telling me something. At my prompting, she revealed that there was one more item on my Fucket List that she wanted to help me with. That’s when she took my hand, led me over to the couch, and began to undress me slowly, deliberately, sensually. My heart was beating out of my chest. I hadn’t imagined being with Monica in that way but once it started happening I couldn’t imagine anything I wanted more. When she kissed me with her full, soft lips I felt a swelling in my stomach. Our tongues mingled slowly at first, but then with lust as her fingers traced my inner thighs, making their way up into my hot cunt. I was already wet with anticipation and spread my legs wider, allowing Monica to caress my throbbing clit and the lips of my pussy while fingering me in a way that had me quivering. My hands literally shook as I unbuttoned her blouse. She wasn’t wearing a bra. Her breasts were surprisingly pert for how voluptuous they were and I suckled them like a baby as Monica worked her magic between my legs. “Tell me before you cum,” she said, “I want to lick your pussy and see you gush.” I’d never before had my cunt fondled with such tenderness. It wasn’t long before I was begging Monica to eat me out. It was clear to me by then that she knew exactly what she was doing and that I was in good hands. She was playful at first, lightly nibbling and tickling my clit with her tongue, then grew more ravenous, licking and sucking me with greater intent as I swelled with arousal, all while fingering my creamy pussy and massaging my g-spot . The orgasm came over me in a massive wave, numbing my toes and causing my legs to spasm. It was so strong that I was literally in shock when it ended. I couldn’t move. With a big smile on her face, Monica put her shirt back on, kissed me on the forehead and covered me with a blanket before leaving.
And with that, my Fucket List was put into action. The world seemed a different place to me. Monica and I were closer than ever, as if we had a special club that no one else belonged to. People at work talked about us in hushed voices and men began to eye me in “that” way. It was empowering. I knew I was ready to venture even further outside of my safety zone. It seemed the most obvious next task to cross off on my Fucket List was to get comfortable showing off my body. This was an easy one, considering there were so many opportunities. I started small, flashing my tits at a passing car here and there, then graduated to wearing short skirts with no panties and opening my legs for drunk men at bars. As sleazy as it sounds, it was a great confidence booster because the men were always so thankful to get an eyeful of what I had down below that they treated me with nothing but respect, often buying me drinks and telling me their sexless sob stories. I learned that it really didn’t matter to men what I looked like as long as I was comfortable in my own skin. Confidence. That was what made great sex. And I was ready for some great sex. On to the next task.

Since I’d already been with a woman and thoroughly enjoyed it, I decided to go for my goal of having a threesome. I found Richard and Sandy on Craigslist. They were a swinging couple in their late thirties and good-looking, but not in an intimidating way. Sandy was an athletically-built, dirty blond with a tattooed chain of roses around her ankle that I loved so much I had to get one myself. I felt very comfortable telling her about my Fucket List on the first night and she was understanding and gentle with me. She loved my thick body, loved sucking on my tits, guided me through licking her pussy and yelped like a puppy when she came. Richard was tall, darkly-complected, and had a huge uncircumsized cock. He, too, was sympathetic to my journey and took it slow with me at first, until I begged him to pound me harder. With Sandy rubbing me, helping me along, Richard managed to pump his rock hard dick into me with such determination that I had the first deep, vaginal orgasm of my life. Jackpot! I was a new woman after that night – a woman who walks with a swag – and there’s no turning back.

Of course, I’m still working on my Fucket List and I have many more sexual adventures to live out. Monica and I are attending a deep-throat workshop this weekend. Yes, there is such a thing, and this grade-A student is going to ace that class. I’ll put my new skills to the test next week when I take that cute guy I’ve been eyeing at the bar home for a ride. If you’d told me a year ago that my sex life would be like this I would’ve called you crazy. I can hardly believe it now. But my high school self believed it, and she’s patting me on the back.