One Night With Amanda

Late-40s, open lesbian. Dyke, butch, stud whatever you call it, I own it all. I live in a LGBT-friendly neighborhood and spend my free weekend nights pursuing women at a few gay bars close by. There is a popular beach nearby which brings in a lot of tourists to my area during summer time, so there is never a shortage of new people to talk to. Sometimes I get lucky, sometimes I don't. However, it does benefit to be a woman approaching other women as I earn their trust quicker than my male counterparts.

The majority of my successes have been with older closet lesbians. These types of women are usually in their late 30s to mid 50s, adventurous and open to having one night stands with strangers, but ultimately not seeking a long term relationship. Some of these women even have families. These ladies are in it for the experience, which gives them a temporary outlet from their mundane lives. Occasionally, I will meet younger, college-aged women looking to experiment. Below is one of my most memorable experiences. This is the story of my encounter with Amanda:

I laid my eyes on Amanda the night before at one of the beach bars I frequently visit, but I had a date that night so I didn't approach her. Even with the dim lighting of the bar patio and distance between us, I could tell from a far that Amanda was a beautiful young woman with a supremely athletic body. Clearly a college girl on vacation with her friends. She was a bit taller than me, maybe 5'7" or 5'8", thin, very well-built, and moved with an athlete's cat-like grace around the dance floor. She had fine features, shoulder length dark-blonde hair and beautifully shaped eyes. She was wearing one of those small beach dresses that night, I could clearly see her perfectly toned body, her high tight bottom and firm belly, her muscular yet shapely calves and slender ankles, she represented the perfect feminine ideal. At least from afar, she seemed friendly and approachable so I told myself I would try to talk to her if I saw her again.

The following night, I saw Amanda again at the same venue. It was getting late and parts of the bar were clearing out. She was standing near the bar, having a drink, and talking to a few people who I assumed were her friends. They all looked like college students. I decided to stand back and wait as these group conversations usually don't last long given how difficult it is to hear over the loud music. This took a lot longer than I had hoped but finally the conversation ended and the group dissipated. Once Amanda was momentarily alone, I took the opportunity to approach her.

My conversations with the women I approach can go many ways, especially in a bar or nightclub setting where everyone has had a few drinks. This was the case with Amanda when I introduced myself. She was clearly drunk, but friendly, talkative, and engaged. She didn't really respond directly to the questions I asked but rather went on a tangent talking about various topics that seemed to pop up in her head. I learned Amanda attended a college out of state and was about to enter her junior year soon. Just as I predicted, she was on vacation with a group of friends. Some of her friends were at nearby bars and others were back at the hotel. She was basically alone at the bar with the exception of a few acquaintances she knew. Our conversation flowed smoothly and I also learned Amanda had recently broken up with her high school boyfriend because she caught him cheating. I could feel the anger in her voice as she talked about her former lover. She was frustrated with the world and in an emotional state.

When asked if she was a lesbian, she responded with "I've only fucked guys before but I think I'm bi," which I thought was a cute response. It's not clear to me if Amanda knew the bar she was in was a well known, local gay bar. I moved on and began asking simpler but direct questions such as if she was looking to "feel a woman" for the first time. Amanda laughed at the question and didn't answer. Maybe she thought I was joking. I bought each of us a cocktail to keep the interaction going. It was just us two talking by the bar at that point.

"I don't think of love as he or she, I just love the person and it doesn't matter if it's a man or woman," Amanda replied while taking a sip of her drink. She explained to me she was taking a break from dating and focusing on college. Given her beauty, it wasn't a surprise there were many guys trying to woo her on campus, but she proudly confessed to me that while she did fancy a few of the boys, she was turning down all applicants in the meantime.

"How do you know if you want a boyfriend or girlfriend for your next relationship?" I asked. Amanda didn't answer again, but this time, I took the opportunity to give her a quick kiss on the cheek. She looked at me and laughed. I joked that maybe she should date women until she is ready to settle down, since women don't cheat, and switch to men afterwards.

From there, it didn't really take much convincing to have Amanda agree to come back to my place for "fancy wine" and "talk some more". Amanda clearly enjoyed the attention and affection I was giving her, and genuinely seemed intrigued about the lesbian world. She viewed herself as a free spirit and taught herself to never judge. She told me she loved trying new things and what life has to offer, simply because she wouldn't know what she liked until she tried it first.

We took a taxi back to my place even though it was only a ten minute walk. It was getting very late and I felt pressured to get something going with Amanda. While in the back of the cab, I had wrapped my arm around Amanda's thin waist, something she didn't even seem to notice. I tried kissing her again but this time she moved her head to the side, dodging my kiss. She giggled but I knew she was probably feeling nervous or even maybe a little regretful. For the remainder of the cab ride, she looked like she was on the verge of falling asleep.

At my apartment, I popped open a bottle of chardonnay and we got settled in the living room. We conversed over wine on the sofa but I quickly noticed Amanda was getting tired and hinted it might be time for her to head back to her hotel. Realizing I needed to move faster or risk losing her, I moved closer to Amanda and kissed her on the lip as she was talking. She was surprised but took it well. Taking it as a positive signal, I gently held Amanda's head in place and went in for a longer, more succulent kiss. I felt Amanda try to pull back initially but I continued on, now holding the back of her head. I could smell the alcohol in her breath as we locked lips. When we finally disengaged, Amanda said she was only looking to go as far as making out, since she hasn't done that in a while and was missing it, but nothing more. She also said she will only stay another fifteen minutes or so and will need to leave given how late it was. I agreed.

Feeling that I had Amanda's full permission to just "make out", I led her up from the sofa so that we were standing before kissing her again. It just felt a lot more comfortable for me standing as we were about the same height. It also helped me plan my next move. She was a lot more receptive and was kissing me back, with her eyes closed, her arms rested by her sides. Amanda was clearly enjoying the session but also very tipsy. I was basically holding her upright with my hands on her hip. She was wobbling and kept moving her feet to find balance.

Escalating further, I pushed down the shoulder straps of her dress and allowed it to drop into a puddle around her ankles. She was wearing a small black bikini underneath. There was even sand still embedded in the bikini fabric from her time at the beach earlier. Barely having time to react, Amanda let out a soft "noooo" in disagreement. "This always happens," she faintly said with her eyes still closed but unresisting. Taking off her skimpy bikini was as easy as pulling on the strings holding them in place and letting gravity do the rest. Now fully in the nude, I laid her gently down on the carpet, stroking her hair, and talking to her in an attempt to soothe her. She barely moved and was very docile. We had already spent a considerable amount of time by then and I could tell Amanda was beginning to trust me more and more.

The bright lights in my living room gave me a chance to fully examine my companion for the night. Amanda's hair was almost long enough to cover her breasts. The breasts themselves were perfectly shaped and not too large, round and smooth-skinned; the nipples were a pale translucent shade of pink. Her arms were long and her hands were delicate, the fingers long and thin, the nails neatly clipped and short. Her face was framed by the cascading waterfall of blonde hair that was almost as perfect as the body. The forehead was broad and clear, the cheekbones high. Her nose was straight and firm and not too large. Her eyes were stunning, large and a deep jade green in color. Her back was smooth, sweeping down from the neck that was always hidden by the flowing hair. Her legs were muscular, long and beautifully shaped, the calves strong, her well-shaped ankles turning down into a pair of high-arched and delicate feet. I could see she had beautifully pedicured feet with her toe nails painted black, her toes straight and long. She clearly put in a lot of effort to look her best on the beach. Her narrow waist was emphasized by the pencil-thin silver belly chain she wore to the beach. She had told me it was a gift to herself for passing all her classes the previous semester.

Her rib cage was high and arched beneath the firm, high-rising breasts; the stomach flat, pierced only by a teardrop shaped navel above her pubis. The hair covering her there was a darker blonde (Amanda was without doubt a natural blonde). It grew in a naturally trimmed and finely shaped wedge that only just covered the soft secret flower between her thighs. Her pubes were so soft and silky, the area begging to be touched. As I stroked her there, Amanda's breathing suddenly changed as I knew it would, adjusting from smooth, long inhalations to quick, shallow gasps of sheer anticipation. I stroked the insides of her thighs with my left hand as my right explored the delights she hid beneath her pubic hair. She made small, animal-like noises between each quick breath as I continued to touch and stroke her there.

Amanda was accepting of my lead. "I'm a little turned on," Amanda softly whimpered. She seemed excited but nervous and embarrassed all at the same time. The soft, lush living room carpets must have felt like heaven to an exhausted Amanda. I grabbed her ankles and easily pulled them apart, spreading her legs wide. I put on my strap-on harness and attached one of the larger dildos I had. Then after quickly applying some lube, I lowered myself onto her flat belly from between her wide-spread thighs. Finally, I moved the dildo towards the opening and slowly pushed it in. Even though I knew that I might have hurt her with the initial penetration, Amanda resolutely and stubbornly accepted the dildo inch by inch until her vaginal muscles had stretched enough to finally accommodate the entire dildo. With the dildo nearly fully in, I started giving her long, slow, deep strokes with my hips. Amanda was breathing heavily but otherwise she was largely silent. However, as I increased the pace of the strokes, she began grunting and moaning.

I could see Amanda's love juices coat the dildo as I slid in and out of her with ease, slamming into her soft yet firm body. She was curling her toes, likely because she felt some pain from the penetration but even more pleasure. I maintained my tempo while simultaneously teasing her clit with a vibrator. The pleasure from the vibrator was clearly too much for Amanda as she shuttered from its contact. I felt Amanda shift her legs and her stomach muscles tighten before she fully embraced the pleasures of her orgasm. It was a beautiful sight. I pulled out my dildo at the last minute in an effort to give her maximum pleasure. Amanda's face was now flushed and her cheeks displayed a light rosy color. Her eyes were closed and her hands were now resting between her legs, covering her flower. Amanda fell quiet as she closed her eyes, either resting or recovering from the orgasm.

It had been great sex but I felt like I had more to offer. Holding Amanda's delicate hands for a brief moment, I slowly lifted them up and had her reveal her sex again. It was slightly more pink than before and very warm to the touch. Lowering my head down and placing my face between her legs, I first give her a kiss on the thigh before pushing my tongue against her clit. As I began moving my tongue, I heard Amanda moan softly and squirm.

"Don't... ahhh, stop," Amanda complains. She was probably still feeling sensitive from earlier. Amanda began using her long legs to push against me while twisting her body to get away from my tongue. Finally I gave up and left Amanda to rest. I could tell from the sound of her breathing that she fell asleep rather quickly afterwards.

She was now lying on her side with one of her arms covering her face, probably trying to protect her eyes from the bright living room lights, and her legs curled up. This posture left her anus exposed. I retrieved a thin, metallic butt plug from my box of toys and lubed it up. I then gently lifted one of her legs slightly, which naturally spread apart Amanda's buttocks and fully exposed her anus. Using just a little pressure, I inserted the lubed butt plug into her unresisting asshole. There was a narrow ring around the end of the plug and her anal sphincter greedily closed itself around the smaller diameter of the plug end. She didn't seem to react to the plug and was sound asleep. However, a moment later, the plug was naturally pushed out. I repeated this process twice until I began feeling tired. I took that as a sign to also get some rest and conclude my night with Amanda.

In the morning, few words were exchanged between us. There was a brief moment where a nude Amanda scrambled across my living room looking for her clothing. While putting back on her small bikini and flimsy dress, she looked embarrassed and nervous. She was likely suffering from a major hangover as well. Ignoring my offers of breakfast and water, Amanda put on her flats at the front door and bolted out of my apartment. From my window, I saw her walk to an intersection up the street and hop in a taxi. It was the last time I saw Amanda.