That Night

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Many thanks to my friend “Kelty”, who was kind enough to edit my first draft. Thanks Bebé!


I met Caitlyn at the birthday party of a mutual friend. In fact, my boyfriend introduced me to her. After my boyfriend manipulated our introduction, I soon learned Caitlyn was bisexual and had a boyfriend; something I’m sure he’d taken into account.

We started talking and seemed to have a lot in common, right down to the fact that we hadn’t tried anything really serious with girls, as we both would consider it cheating. Although we often took the submissive role in our current relationships, Caitlyn was the likely submissive while playing with a woman. Our similarities created a strong beginning to our friendship, while our differences were entertaining.

A month after I met her, we decided to take the boyfriends out to dinner, to see if they got along as well. Inevitably, the topic turned to sex. Typical men. Caitlyn’s boyfriend explained his desire to let her be with another woman. He understood she considered it cheating, but figured if he could watch, it wouldn’t count, especially since Caitlyn had his direct approval of the deed. Caitlyn didn’t want him to be there the first time. She figured it would be too much like a performance if he was around. Stalemate.

It was my boyfriend who came up with the solution. Aware of Caitlyn’s submissive nature, he suggested that her boyfriend persuade her to be with a woman, making sure the woman was dominate so Caitlyn couldn’t argue. At that point, I was beginning to feel set up, and oddly enough, a little turned on.

In the past, my boyfriend had expressed his desire to see me with another woman. It was one of those things he never really pressured about, but always presented as an option. I asked him whether or not he’d planned this. The sudden redness along his cheek bones and ear lobes said more than his stilted speech could have ever confessed.

And yet, I was intrigued. Obviously, the boys had planned this. At the moment I wasn’t particularly interested to find out how, but I was definitely intrigued by the possibilities. The boys set it up; therefore, the boys say its okay. It was more like giving in to the demands of my “dominant partner”, rather than cheating on my boyfriend. Especially if he watched someday in the future. Not the first time, of course, I was with Caitlyn on the idea of not creating a performance. I wanted my first time going all the way with a woman to be no holds barred, not “hold that pose while they take it in”. Now all I had to do was convince Caitlyn to come around to my point of view. From the excitement building in her eyes, it would not a terribly difficult job.

I decided that convincing her would have to be a physical task. I was sitting next to her, so I put my hand high on her thigh, delightfully bare beneath a short skirt, and waited for her to look at me. Which she did with rapidity and some surprise.

“Gwy, what are you…” she started, but before she could finish her sentence, I leaned over and took her mouth. Unexpectedly, she welcomed my tongue as it delved between her lips, and was soon moaning quietly while my tongue stroked hers in an imitation of the mating ritual. I pulled back a moment later, to see her skin flushed a rosy pink, and the men undecided on whether to gawk or cat call.

My boyfriend broke the silence first. “Thank God that we’re in a dark restaurant… Well, I guess Gwylan’s in. It’s all up to yours now,” he observed, directing his comments to Caitlyn’s boyfriend.

“She’s in too,” came the response, before Caitlyn could even muster up the breath to form a protest. What can I say; I’m rather proud of my kissing technique.

“What do you say? Tonight?” My boyfriend asked, directing the question at the appropriate person.

Caitlyn’s boyfriend nodded. atakent escort “Definitely.”

Caitlyn looked at me, and I winked at her. We smiled. Tonight would be very interesting.

The meal ended quickly after that, as if anticipation made eating just another thing to get out of the way. Caitlyn and I left the restaurant talking quietly together, while the boys trailed behind. I’m sure they thought we were teasing each other with promises for tonight, but really, we were planning where to meet once we lost the men trailing behind us. We decided on a motel not far from either of our apartments, and split up to go drop the would-be voyeurs off at home, and change into something a little less formal.

When my boyfriend and I arrived back at our apartment, he pulled me close to him, and looked into my eyes. “Baby, I know we’ve talked about you doing this for a while, but I want you to know, you don’t have to go through with it if you don’t want to.”

I looked at him, and could tell he meant it, even though this had been one of his fantasies for as long as we’d been together. I smiled at him, and told him that I was ready for this, and that I was glad for his support. I quickly changed, gave him a kiss, grabbed my purse and left the apartment.

I pulled up outside the motel with my knees shaking and my hands a little unsteady. Sheesh, I felt like a virgin again, only this time, I didn’t have Sex Ed to fall back on. I looked around for Caitlyn’s car, and not spotting it, went and rented a room for the night. Typical motel room, but with one outstanding feature. The management had just replaced the mattress.

I had to bounce on it a couple times, just to make sure it was up to my standards, of course. To be honest, I had to relieve some of the tension that was building with every moment I was in the room. I heard a car pull up outside and fleetingly wondered what Caitlyn had told the night clerk to get in a room I had just rented.

I figured I might as well start the night off properly, so I met Caitlyn at the door, pulled her into the room, and sat her down on the visitors’ chair. I looked her in the eyes and told her she had one last chance. Leave now, or don’t leave until morning. Her whispered, “Stay”, was barely out of her mouth before I caught those lips against my own, and dragged her flush against my decidedly aroused body. Decidedly aroused? Hell! I was pretty sure I had soaked my way through my panties and was starting on my jeans!

I pulled her slowly to the bed, kissing her almost continuously; slightly afraid she’d still change her mind and bolt. We made it to the bed and I moved the two of us into a sitting position on the edge of the mattress. For a few moments we just looked at each other, and I came to a decision. I consider domination to be a relationship choice; I chose to start this one without it.

I moved closer to Caitlyn and gave her a quick peck on the lips, and she seemed to be puzzled when I pulled back.

“Gwy, what are you doing? Why are you teasing me?”

“Caitlyn, we already have partners that satisfy the part that needs a spanking every once in a while. Why can’t we just be intimate friends? Equals.”

Caitlyn frowned a little, pulling her forehead into a cute little furrow that I longed to smooth out. In all honesty, I sometimes felt very protective of her; she seemed so petite and confused. Then her face cleared, and she gave a smile that reminded me that hidden behind that pixie face was a black belt ass kicker.

“Gwylan, I think that’s an excellent idea. You being in charge might have put a cramp in my plans for tonight. I want to be able to touch you, taste you, lick you all over, and I damn well don’t want to ask to do it. Come here.”

I leaned over, expecting a reciprocation of my earlier welcome, and ataköy escort I wasn’t disappointed. Practically grabbing me by the ears, Caitlyn pulled me down on top of her, crossways on the bed. Her agile tongue teased my own , slipped in and out of my lips, flicked against my tongue , swirled along the corner of my mouth, and every once in a while, skipped lightly across my lower lip before diving back into the melee. And I thought I could kiss!

Through the haze of increasing horniness, I realized she was running her hands lightly up and down my sides, and along my lower back, growing familiar with the curves of spine and hips. I wondered if she did it naturally in appreciation of a good kiss, or whether she was unconsciously finding the best places to use as hand holds later on.

A few seconds later, I think became overrated as Caitlyn decided that being on the bottom was not going to suit her needs, and rolled with me to switch our positions. Her kiss was broken in the process, but her lips roamed my collar bone and neck, and I began to moan. God I love that! My nipples tightened, and my already more than dripping pussy began a low throb.

Caitlyn reached to unbutton my shirt, and pulled slightly away from my hypersensitive flesh. Without the contact of her mouth, I realized that my hands were able to do more than convulsively grasp her hair. I reached for her shirt, thankfully a pull over because, while I could move my hands and arms, they just weren’t up to the challenge of buttons. Hell, snaps might be a problem.

“God, Gwylan. You were twitching like a bug on raid.” Caitlyn smiled a little, obviously delighted that I was so responsive.

“My neck is hypersensitive. Jack likes to sneak up behind me and nibble on my neck too. He knows it’ll get me going. It’s like guaranteed sex, cause it makes me so wet.” I giggled, “Jack says I twitch like a fish out of water, but I think I like your analogy better.”

Caitlyn giggled a little too, but she’d finally gotten to the last button on my shirt, so neither of us was laughing long. Soon, I was teasing her nipples with my fingers and moaning, while she used her amazing mouth on my tits. And if my boobs were jealous of my lips before, my lips were now gasping their envy. With more flesh to play with, and the ability to get her hands involved, Caitlyn was quickly proving herself to be my favourite breast fondler. She licked, nibbled, bit, tugged, pulled and sucked on my tits, paying close attention to my nipples but definitely making the rest feel included. In between her licks and sucks, she let out a moan as I pulled and tugged her nipples, lifting and rubbing her titties with as much pleasure as I was getting from her manipulations.

I quickly reached the edge of my tolerance for merely that type of play. While Caitlyn seemed happy enough to sit and suck my boobies all night (a thought I filed away for later), I was ready to move to the part that I’d wanted to try for a long time. I flipped her small body over, and kissed her again, reaching between our bodies for the tab of her jeans. I lowered the zipper and flipped loose the button, thankful that women didn’t have junk that got caught in the fly.

Caitlyn arched into my fingers when I dipped them into the crease at the top of her soaked pussy. I quickly pulled her jeans down and off her body, take a few moments to nip the insides of her knees during the process, and to enjoy the view of her naked body arching toward me. From my VIP seat between her knees, I could see the juice dripping slowly down the crease of her ass, and the tension of her muscles as she waited for my verdict.

“Well? Do you like it? We can stop if you don’t want to go any further. I-” Caitlyn’s nervous monologue was cut off with a quick kiss to her talking lips, and a glide of my finger along the atalar escort lips under discussion.

“Caitlyn, I think it’s beautiful. In fact, I think it’s so pretty, I have to kiss it.” I could see the visible relaxation of Caitlyn’s muscles as she smiled at my corny attempt at humour, and she pulled her legs further apart as I looked down on her once again. Just to make sure she wasn’t going to bolt, I began to lick her nipples first, drawing them to hard points on her palm sized tits. I worked my way down her body, nibbling the underside of her rib cage, swirling in her belly button, until I reached the point at the top of the crease that I had dipped my fingers into a few minutes earlier. I licked the plump outer lips of her vulva, avoiding the centre which was decorated in a simple line of dark hair that matched the deep black of her ponytail. I bit gently at the inside of her thighs, enjoying her part squeal, part half-breath that she seem unable to control. Her hands were soon wrapped in my falling down bun, pulling my head towards the magic button at the top of her slit.

For a while I resisted. I enjoyed the tugging on my hair, sure, but the best part was listening to the breathy moans, and helpless whimpers coming from her parted lips. I moved my own mouth back to the top of the nearly hairless mound, and began to slide my tongue in long sweeping glides from the top of her thigh, down into the crease of her leg and her slit, and back up again on the other side. With every sweep, my tongue was bombarded with her juice. It was sweet and tangy at the same time, different from what I was used to, but definitely just as good. A sharp tug on my head brought me away from that train of thought, and firmly back to where she thought it should be. Focused on her pussy.

I decided to try one of the tricks that I was incredibly fond of. I sucked on the lips of her cunny, pulling them away from her body, and then let them go with a snap that created a soft tap on her clit. Her startled but appreciative moans indicated that I should do it again, and so for a few minutes I repeated the move, interspersing it with a quick lick to the button in the centre. Soon, though, my tiring tongue told me that it was time to get on with the main event.

I began to flick my tongue back and forth, up and down on her clit, while slowly sliding two fingers into her wet slit. Still teasing her button, I sped up my finger movements until I felt the tell-tale irregular clutching around my fingers. Swiftly, I curled my fingers up, dragging them along the spongy ceiling of her pussy, while almost simultaneously sealing my lips around her clit to suck hard.

She exploded. She contracted so powerfully around my fingers I knew I would lose one if I tried to pull them out. She screamed so loud that ten minutes later I was still waiting for the night manager to show up to investigate, and her face reminded me of a circus clown.

She was beautiful. Laying there limp, and from the look of it, completely sated, I was feeling very smug. I crawled up close, pulling her into my arms. We kissed lightly, both a little short of breath, and she rested her head on my breast.

“God, Gwy… That was fantastic. I mean my boyfriends great, but WOW! It pays to have insider knowledge.”

I laughed. “I admit I didn’t come up with all that myself, but I definitely like knowing where the good spots are.” I kissed her again, and noticed her tongue was an enthusiastic participant, but the rest of her seem a little wiped out. “Okay, Caitlyn. Bed time.”

She giggled. “I am in bed.”

I grinned, and explained, “I mean, time for sleep.”

“Gwy… but what about you? I can –“

“Don’t worry about it. We have ‘til tomorrow at one in here. And lots of time after that. I‘ll be fine. It‘s not the first time I’ve had ‘blue balls’.” She giggled at that, and snuggled down lower on the bed.

I pulled the covers off the bed and we tucked ourselves in. Caitlyn promised to fix my “problem” in the morning and the fell fast asleep. Wrestling my share of the covers back, I glanced down at my friend and new playmate. I smiled. What can I say? I’m rather proud of my kissing technique.

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