Enjoying Sex With Men…As A Lesbian

    Alexandria Fox · January 22, 2017 · The Smut Files · 0 comments

    Yep you read that right. On occasion…well rarely I will seek out a man for sex. By rarely, I mean that the last time it happened was in December 2012 and while on holiday in Puerto Rico I met a beautiful Portuguese and Belgian surfer there on holiday as well.

    It was a warm Saturday night and I decided to wander down Avenida Ashford in the Condado Beach area to one of the local bars recommended a day earlier by some locals I hung out with on the beach that day. I walked in and immediately across the room I spotted a guy with his back to me who was just a bit taller than me with waist-length blondish-brown dreads. When he turned around, I was struck by how beautiful he was. His face was clean shaven, chiseled Castilian perfection and from his features I could tell he was European—just my type. I locked eyes with him from across the room and headed across the dance floor filled with pulsating bodies gyrating to Reggaeton and said to him, “My name is __________, I want to buy you a drink and then fuck you in my room for the rest of the night and if it is good, for the rest of my stay in Puerto Rico.” I have never been one to dance around my desires and least of all when it came to men I fancied. By 2012 it had already been seven years since I last had civilian sex with a man or desired to. I had been living and enjoying life as a lesbian and outside of sex work, sex with men was rarely a thought. Nonetheless, here I was face-to-face with a guy who had all the hallmarks of masculine beauty that I lusted after.

    “Ummm…ok”, he stammered, “My name is J”, and he stuck out his hand to shake mine with a puzzled and amused expression on his face. “Perhaps if you are good, I will take you around the world as I travel from country to country the next few months.” He stated, eyeing me up and down and wondering what I was all about.

    We talked and had a few more drinks and as the night went on we both realized we shared a great

    At the beach!


    deal in common and that the sexual chemistry was off the charts. We talked so long that soon the bar/club was due to close and he and the friends he was with walked me back to my hotel as the house they were renting was only one street over. Everyone said their good-byes and before we even got on the elevator our hands were tearing at each other’s clothes, our lips expressing the lust between us, and his hands were in my underwear. He ran his fingers between my thighs and licked them as he looked into my eyes…we were in for a long night. Needless to say, he fucked me and I fucked him (more on that later) until about 11am.

    While showering together he asked what made me select him out of all the men at the bar.  Pressing my naked body against his in the shower, I took a step back and while gazing at his sinewy back and buttocks and noticing how androgynous his frame was I said, “I wanted to have sex with a man despite being a lesbian.” He turned around. The water ran down his caramel colored abs and he looked at me with mischief in his greenish brown eyes. “Ha! I figured you were a lesbian! I seem to attract them. I’m open sexually. Not bi but not sexually straight…I’m simply open to experiencing the pleasures that sex brings.” He closed his eyes and leaned back under the water. I swooned, I sighed headily and feeling almost sexually famished, I got down on my knees and took his already erect cock into my mouth. He moaned something in Portuguese while grabbing my hair and arching his back. I relished the feel and the personally appropriate size of his cock in my mouth. Not too long and definitely enough girth to surprise a girl on entry. I sucked until he came, rose from my knees, and shoved my tongue violently in his mouth as he lapped up his own cum. We drove each other crazy and we knew it…I continue to speak to this guy to this very day and when I am in Europe summer 2017 I plan on stopping by his new bed and breakfast just south of Lisbon, Portugal and fucking his brains out once more.

    Having sex with men and enjoying sex with men as a lesbian is nothing new. There are women who write about it from their various viewpoints here, here and here. This, however; is my story and my viewpoint: I have sex with men as a sex worker and as I have told many a man who either eventually discovers I am lesbian or reads it on my blog that:

    • Sexual response begins in the mind but is eventually an autonomic nervous system response with enough nerve stimulation. If a person knows their way sexually around a human body, they will eventually stimulate nerve endings in the erogenous zones enough to produce arousal and eventual orgasm.
    • Overcoming the mental part lies in reframing one’s personal narrative concerning their sexuality, what one finds attractive, and letting go of traditional/societal/familial beliefs around sex.

    Point two, is especially true for men as sexual acts are tied up with masculine/machismo identity  and being penetrated by another man or giving a blow job to another man is deemed a homosexual act (read: woman’s duty) and thus causes mental distress in the form of cognitive dissonance for most straight men. It is seen as “gay or bi” to engage in traditionally “gay” sex acts as a man. Even if these are done with a woman. I have heard both women and men (even sex workers) describe a straight man who enjoys or is curious about pegging as closeted gay or bisexual. I cringe and am secretly angry when I hear that because how come it is so foreign that such and such person might simply be enjoying the pleasures that aroused human flesh and stimulated nerve endings brings and that this has no bearing on that individuals’ overall identity?!

    • Homo, hetero, and bisexuality are more about who you want to pair up with and less about sex. Let’s use the new terms of Hetero-living, Homo-living and Bi-living.

    What I mean is that each of us has who we would prefer to share the mundane aspect of life with. I can’t stress this third point enough. Who do you want to roll over and look at every morning, live with, nag about taking out the trash or drag along to friends and family gatherings and holidays, and who do you want to share your joys and sorrows with that come with life? That is what all the homo-hetero-bi business is all about. This is the point that the LGBTQ+ community has been trying to make for decades to the hetero-living world while the heteros focused on the smaller aspect of sexual acts. Ultimately, life as a human is about pair bonding and social connection. We are deeply social creatures who quickly descend into madness without social contact (source) and imagine if you will, living your life as a lie (being deprived of the social contact and love you crave) and suffering under the weight of all that. That is the number one reason LGBTQ+ youth have some of the highest suicide rates in this country (source).

    • Yes, who you want to have sex with and are sexually attracted to is a part of all this, but it is the smallest part for many of us.

    Human sexuality and sexual response exists on a continuum. The 100% hetero and 100% homo people are on the opposite ends of the scale and everyone else falls in the middle in various shades of the human sexuality rainbow. The graph is not a bell curve because as we all know, most people are hetero-living but there are variations within heterosexuality. Among the homo-living and bi-living there is also variation.

    I am one of those variations…

    I prefer to share the mundane aspects of life with women. I prefer to have sex with women. I have enjoyed amazing sex with men as a sex worker and detailed above an amazing sexual experience I have had with a man while on holiday. I am aware of the fact that there is a high possibility that I will have sex with a man outside of sex work and enjoy every minute or hour of it. I regularly have awesome sex with and thoroughly enjoy the company of the men I meet as a companion.

    None of this infringes on me being a lesbian and I am not bisexual because I do not date men or have emotional relationships with them in my personal life.

    I have met some of the most amazing men as a sex worker. Men who I converse regularly with, grab dinner and drinks with, take trips with and who I enjoy fucking. They have feelings for me and I have feelings for them. We take care of each other and fulfill the needs of each other. These are men who get it, whose manhood is not insulted by the above because they are emotionally and socially astute enough to understand that the world does not revolve around men, a man’s viewpoint and a man’s needs and insecurities. My definition of my sexuality is of no consequence or threat to them. We simply enjoy our time together and that is it.

    So back to my gorgeous Portuguese-Belgian surfer.

    He left later that day as he had a children’s surfing clinic to teach. Afterall, that was what he was in Puerto Rico for. We made plans to rendezvous back at my place at an undetermined time in the eveing. I spent my day shopping in old San Juan, on the beach and hit the La Placita for the salsa bars for some dancing. There were tons of hot women but J stood out in my mind. Around 11pm I received a naked picture of him via text in my bed with my strap on laying next him. The next text read. “Come fuck me.”

    I hailed a cab back to my hotel on Ashford and my cunt throbbed with desire the entire ride there. I opened the door to my room to find he had opened the ocean front balcony and brought with him some lamps that provided dim light for ambiance. He met me at the door and lifted me off my feet and threw me onto the bed. “I want you while you still smell of dancing and desire.” I really wanted to take a shower before our evening romp as I smelled of salt and cigars but he was soon eating my pussy through my panties and moaning loudly. After I came, he poured himself a glass of rum and walked naked to the balcony. “We’re you surprised to find me here again?” he asked. “Yes acutally…I am very surprised. I figured we were one and done.” I replied as I shimmied out of my dress still wanting a shower. “I found your strap on…”, he paused. It seemed a pregnant, slightly frustrated pause. “…was that meant for a woman or a man?” I saw that he was curiously frustrated within himself by my motives and apparently had been through the sex drawer in my room. I pushed him down into one of the chairs and sat on his lap, “What is in my sex drawer is for whomever happens to find themselves in my room…male…or female.” I took a sip of his rum and looked out over the ocean. I could’ve sat there forever with him.

    “I want to experience that with you. I am curious and it is the one thing I have not done with a woman.” I looked over at him. He was smiling looking out over the ocean as he said it. He continued, “I have been with men before, but I am not gay…I sense you know this…I don’t know why I feel the need to tell you.” I nodded, still enjoying the view and the smell of salt in the air. I could see light from a fire on the beach. “Yes…yes I know and if you were, I wouldn’t care. We are whatever and whomever we choose to be behind closed doors. I believe that pleasures unexplored are pleasures denied the flesh.” He kissed me with a passion still felt by my soul to this day. If there is a such thing as falling in love from a kiss, well…that was it in every sense of the word.

    I got up and went back to the bed and stepped into the harness of my strap on. I called him to me from the balcony. In the dim light of the room, his ocean hewn body was that of a demi-god. His cock hardend at the sight of me. I kissed him and then turned him around and began to stroke his cock from behind rubbing my dildo just as a man would do a woman into the cleft of his ass as he moaned. “Mmmm…it pleases me that you like that. Are you going to be my little slut tonight?” I whispered into his ear. He replied with a moan as I bent him over the edge of the bed and slowly began to work my way into his tight little hole. Once in his breathing shook. “Shhh…I will go nice and slow.” I said, as I began thrusting movements. I have never been so turned on fucking a man with my strap on in my life! His moans of pleasure and desire with each thrust were delicious and soon my juices were running down my leg. I fucked him from behind and fucked him missionary with his legs wrapped around me. I watched him orgasm without cumming several times before he simply couldn’t take anymore and shot loads of cum all over his chest and the bed. “Be a good girl and lick it up.” He said to me, at which I happily obliged…he also got down and licked my cock clean not that there was any mess but he still sucked it with full eye contact.

    Fast forward five years later and I sent this blog posting to him while it was still a draft. He laughed and said, “I’ve thought about that weekend as your sex toy all these years. Now that you speak a little Portuguese, when you come to Europe we will have to repeat this while speaking my language because it will sound so much sexier when we cum.”

    Indeed it will, J, indeed it will.

    Written by Alexandria Fox

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