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Holiday Hotel Encounter

Category: Group Sex
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We were in the hotel bar having a post dinner drink when an older couple (we were mid 20s, they were late 40s I would say) approached us (I can’t remember their names so I’ll call them Jim and Pam). Anyway, they introduced themselves, said they’d noticed us by the pool and in the restaurant and had seen us out in the local town during the day.

They bought us a drink and joined us at the bar and for a little while we exchanged stories about our day in the town, what else we had done and our plans for the remainder of the holiday.

After a little while my boyfriend, Steve, and Pam got into a discussion about books & authors and Jim & I were discussing holidays, cultures, etc. As we started our second drink Jim suggested we move to the seats (more like sofas) away from the bar. The two of us made our way over but Steve and Pam were so engrossed they didn’t notice. Jim was slightly touchy-feely as we moved but I didn’t make an issue of it.

After we sat in the slightly darker area where the sofas were, Jim was very solicitous, staring at me, paying attention to what I was saying, very animated in his responses, touching my arm, etc. At one point he took my hand in his and when he finished what he was saying he put my hand on his leg and returned the compliment by putting his hand on my thigh. I realised what he had done when I could detect a slight bulge under my fingers and I felt his hand stroke my thigh gently.

I remember looking towards Steve & Pam and she was also being touchy-feely with him but they were not looking in our direction. When I looked at Jim again, he was taking a sip of his drink and looking in the opposite direction, apparently not aware of any impropriety. As I reached for my glass (leaving my hand on his leg) and took quite a large drink of Malibu or Bacardi (I think) I felt his fingers make contact with the skin of my upper thigh and realised that he had subtly worked his hand into the slit of the wrap around skirt I was wearing.

I became a little nervous but at the same time excited. Steve and I had had our fun in our cars, kissed and hugged on trains & the underground and even petted each other subtly in the pub at home. But, now, a relative stranger was touching my flesh in quite a public place. At the back of my mind, though, I was thinking that very little could really happen in the hotel bar. I decided to push my boundaries a little.

As his fingers stroked my thigh I built up my courage and eventually allowed my fingers to drift up his leg. I actually felt his penis grow a little and he edged closer to me. With his right hand perilously close to my groin I started feeling a little flushed. With his left hand he pressed my left hand against his leg & penis and somehow manoeuvred things so that his penis was no longer down his trouser leg, but was up around his zip. He then lowered his zip himself and opened his fly. I loosened the button of his trousers, peeled back the side nearest to me and found myself touching his penis because he was not wearing any underwear.

Up until then I’d never thought about not wearing underwear but afterwards I remember encouraging Steve to do something similar for some of our special dates.

As soon as my fingers touched Jim’s penis it pulsed and grew. I was touching a ‘new’ erect penis for the first time since I’d started dating Steve. Jim’s right hand now moved down my left leg and applied pressure, pulling it towards him and eventually over his right thigh and using his left leg to trap my foot. Of course that meant that my whole left leg was actually out of the split in my skirt.

Immediately, his fingers moved back up my thigh. Just the touch of his fingertips on my thigh caused my skin to goose-bump and I couldn’t help but shiver a little. As soon as he reached the join of my leg and groin his fingers moved in and down, floated over the outside of my panties and down to my sex. He took pleasure in trailing his fingers up and down the gusset of my panties and pressing slightly every now and then. He managed to work my panties between my outer lips and right over my slit. I could only imagine how damp they were becoming.

Each time his fingers reached the area of my clit he pressed firmly. I was moving my bum around on the sofa and pressing against his fingers when I could.

The illicitness of the episode got to me and he didn’t even get his fingers inside my panties before I felt an intense orgasm hit me. I think I bit down on my lip quite hard to ensure that I didn’t make any noise but I know my body jerked and shuddered a few times.

I suddenly realised what had happened and felt myself blush. Then I noticed that I was gripping Jim’s penis and stroking it. As I ran my thumb over the tip I felt pre-cum leaking from it and enjoyed spreading it over the head of Jim’s penis. After only a few strokes, though, Jim’s hand stopped me and he admitted that if I continued he would ‘make a mess’ and he didn’t really want to do that at the table. He suggested we go for a walk in the hotel gardens.

I suddenly remembered Steve and I looked towards the bar again. Pam and Steve seemed to be sitting much closer and were both turned more or less towards the bar. I breathed a sigh of relief that they hadn’t seen what we had been doing. I felt Jim’s hand on my thigh again and he repeated his suggestion. I wasn’t so naive that I didn’t realise he would expect a little ‘repayment’ in the gardens but I hesitated only briefly before agreeing.

I looked down and saw that Jim had made himself decent. I pulled my skirt together and took Jim’s hand as he helped me out of my seat.

I was surprised that Pam and Steve had not spotted us getting up. When we reached them however they looked around in surprise and Steve had his classic innocent / guilty, deer in the headlights, expression. I saw Steve’s arm move and looked down to their laps. I’m not sure whether I was surprised when I saw Pam’s fingers wrapped around Steve’s penis, slowly moving up and down its length.

Steve blushed bright red and opened his mouth but before he could say anything stupid I pressed my fingers to his lips and shushed him. I then bent down and kissed him, my lips gently touching his, and I heard Jim saying that we were going outside for some air. Steve looked at me mutely, his mouth opening and closing but no sound coming out. From the corner of my eye I could see Pam’s hand continuing to move up and down Steve’s penis as she told Jim that they were okay for the moment and that she hoped we enjoyed our walk.

Once we exited the hotel Jim took hold of my hand and led me to a secluded part of the garden. As soon as he was sure we could not be seen by anyone he stopped, turned towards me and kissed me. I momentarily lost myself in the kiss. I could feel my heart pounding in my breast. The intensity of the kisses gradually increased. His tongue nudged into my mouth and I welcomed it.

His hands caressed my arms and moved to my shoulders. He moved me away from him slightly, creating a gap between us that allowed his hands to drop down and across the front of my blouse. My nipples were prominent through the material and he brushed his hands back and fore over them. His fingers reached the buttons on my blouse. As he slowly undid each button my sense of excitement increased.

There were only four buttons but it seemed to take an age before Jim separated the sides of my blouse and peeled them back off my shoulders, exposing my breasts. He released the blouse and his hands cupped my breasts. His thumbs flicked across my nipples and I gasped at the sensations. He knew exactly what to do, alternating between pinching my nipples and flicking them. I was revelling in the sensations again when he stopped and I groaned in frustration. I felt Jim ease the blouse down my arms and I allowed him to remove it completely.

My release from the sensations he had been causing galvanised me. I moved in against Jim and pressed myself against his crotch. His penis was hard again and now it was my turn to play. I loosened the buttons of his shirt and exposed his chest in the same way he had exposed my breasts. I ran my fingers through the dark hair on his chest, contrasting the sensation with that from Steve’s smooth chest.

I removed Jim’s shirt then reached down to his trousers. I loosened the button and then lowered the zip. His penis had been erect against his groin and it fell forward as it escaped from the confines of his trousers. I bent down to lower Jim’s trousers down his thighs and they then fell and pooled at his feet.

I reached forward and gently touched Jim’s penis. It was leaking pre-cum again. I used one hand to stroke Jim’s penis and raked my finger nails of my other hand across his balls. After a few minutes he starting speaking quietly to me, telling me how nice it felt. I was looking down, watching my hands playing with him when I felt his hands pressing gently on my shoulders.

I suspected he wanted me to give him a blowjob but I had only done that a few times with Steve and wasn’t particularly experienced. I whispered that I wasn’t sure about doing that but he encouraged me with his own quiet words. When I released his penis so that I could rest my hands against his hips to lower myself down, it was Jim’s turn to groan with frustration.

Although we were on grass I still wanted something to rest my knees on. I bundled Jim’s shirt up, placed it on the ground and rested my knees on it. Once I was set I looked ahead and slightly down and was staring at Jim’s penis, bobbing before me in the night air. I took a gentle hold of it and pointed it towards my mouth. I looked up and Jim was watching me intently.

I asked Jim to close his eyes or to look away. I sensed disappointment but he did as I asked. I opened my mouth slightly and blew gently. Steve had told me that that felt very nice and Jim’s moan confirmed that he enjoyed it too. I poked my tongue out of my mouth and edged towards the tip of Jim’s penis.

When my tongue made contact Jim’s penis jerked even though I was still holding it and I squealed in surprise. Jim apologised and breathed deeply then asked me to try again. I did exactly the same second time around. This time, when my tongue touched Jim’s penis it moved only slightly and I was able to lick the drops of pre-cum gathering at its tip.

I slowly played my tongue around the tip then formed an ‘o’ with my lips and kissed the head. Jim moaned again. I slowly opened my mouth and edged my head forwards so that Jim’s penis was fed between my lips into my mouth. Once I had a couple of inches in my mouth, resting on my tongue I reversed direction until Jim’s penis was fully exposed to the night air.

I moved my head forward again. This time I took more into my mouth. I felt Jim trembling and I thought he was battling with himself. It seemed that, on the one hand he wanted to thrust himself inside my mouth, but he also wanted to show himself as considerate to this young, slightly inexperienced girl. I was grateful for that and determined to give him pleasure.

I continued to work slowly on Jim’s penis. Then I moved one of my hands to his balls. I cupped them gently as I moved my head slowly backwards and forwards on him. Jim’s hands moved to my head and he started moving his hips. Again, though, his movements were slow and deliberate. I raked my finger nails across his balls and that was greeted with a moan that was louder than anything he had uttered previously.

I sensed that he was about to cum so I resisted his hands and removed my mouth from his penis. I started stroking him with my right hand whilst playing with his balls with my left hand. His hips started moving more vigorously so I edged to the side and turned him a little. Then he suddenly thrust his hips forwards and groaned as the first spurt of sperm came out. I continued to stroke his penis and tickle his balls and two or three more spurts emerged. The last two weren’t really spurts, more leakages which oozed down his penis and over my hand.

As Jim leaned back against a tree to recover I wiped my hand on the grass. I realised that I had left my purse with Steve so I didn’t have any tissues, nor did Jim have a handkerchief. I still don’t know why I did it but I stood up in front of Jim and told him to reach under my skirt and remove my panties.

Having started to soften, Jim’s penis jerked a couple of times, apparently coming back to life. As he removed my panties he took the liberty of trailing his fingers over and through my pussy lips. As I enjoyed the feelings I looked off to one side and saw Pam and Steve. Pam was in more or less the same position I had been and Steve was leaning back against a table as she bobbed her head backwards and forwards on his penis.

The thought went through my head that it was the first time that I had ever seen someone else having sex, and one of them was my own lover. Surprisingly I was quite thrilled at the sight.

Jim held my panties in front of him. I used them to remove that last of his sperm from my hand and then wiped his penis with them. Of course that resulted in it continuing to harden. I continued to stroke him as we watched our partners. I spotted the signs of Steve’s impending orgasm and heard him tell Pam that he was about to cum.

Pam just continued working on him. Then as he groaned she pulled him forwards so that his penis was completely in her mouth. I watched as Steve’s hips jerked and I knew he was cumming in her mouth. Pam just kept her mouth clamped around him and swallowed his sperm. I was momentarily shocked and slightly intimidated given that I had finished Jim off by hand but quickly decided that we do what we are comfortable with and Jim did not seem to be complaining.

When Steve had finished cumming Pam released his penis. He opened his eyes and saw us watching him. Even in the reduce light of the garden I could tell that he was blushing. I remembered why I loved him so much.

Jim pulled his trousers up and we made our way across to our partners. Jim and I held out our hands and helped Pam stand up. As Steve bent down to pull his underwear and trousers up.

Once Pam was standing Jim released her hand but she kept hold of mine. Then, with her other hand she reached out and pressed her palm against my breast, crushing the nipple and breast and causing my knees to go weak. I had forgotten that I wasn’t wearing my blouse and I was still sexually aroused. Pam released the hand she had been holding then moved towards me. Her arm went around my back and she pulled me towards her. Our lips met. I groaned with pleasure tasted Steve on her mouth and she continued to play with my breast.

I felt someone behind me then hands at my hips. Pam moved her body away from mine and my skirt dropped and pooled around my feet. I was drunk with pleasure, naked except for my shoes in front of three people, two of whom were more or less strangers. I definitely hadn’t expected this when Steve and I planned our holiday.

I vaguely heard someone mention “risk” and “room” and was somewhat disappointed as I felt my skirt being wrapped around me again and then my arms being manoeuvred into my blouse. I was in something of a stupor as I was led away from the hotel gardens.

We very quickly arrived at Pam and Jim’s suite. It was a one bedroom apartment with a lounge area containing a sofa and two chairs, and a dining area containing a table and four chairs.

I started to make my way to the sofa when I was brought to a halt. Through my pleasurable haze I felt my clothes being removed again then I was manoeuvred towards the table. I stood with the backs of my thighs resting against it. I watched as Steve and Jim stripped out of their clothes. When they stood next to each other it was quite a contrast: Steve’s young, slim, smooth body compared with Jim’s older, solid, hairier shape.

My eyes drifted to their groins. Both penises were erect – perhaps Steve wasn’t as shy as he made out – and were quite similar. Steve had perhaps a little extra length and girth but not a lot. I sniggered to myself as I wondered if Jim’s had been worn away a little by his experiences. Just looking at their two bodies and penises was increasing my arousal. I suddenly realised that one of my hands was absentmindedly touching and playing with my own breast. I hadn’t been aware of moving my hand but I must have done.

I detected motion from the corner of my eye and then Pam appeared. She was dressed in a white bathrobe. She turned to face me then looked over her shoulder and nodded. Hands reached around from behind her and loosened the belt on the robe. The hands then moved to her shoulders and edged the robe off them. Pam shook her body and the robe dropped away. I wasn’t surprised to see that she was naked underneath. Considering her age her body looked wonderful. I briefly expressed a silent wish to be in such good shape at her age.

I did notice that her breasts were not as perky as mine but her large nipples were already pointing straight ahead.

Pam walked towards me. There was no hesitation. Our bodies came into contact. Our breasts mashed against each other. Our lips met. She kissed me tenderly at first, then passionately. Her tongue edged into my mouth. Her hands worked between us and made contact with my breasts. I returned the compliment, reaching up to play with hers. I flicked and pinched her nipples as Jim had earlier done to me. She moaned as I played. I don’t know how long our embrace lasted, but I remember feeling my arms levered from Pam’s body and being stretched outwards to the sides.

My arms were slowly moved back and I was lifted slightly so that my bum rested on the edge of the table. My arms were raised and I was pulled back until I was laid back on the table. My legs were mostly off the table but they had opened slightly to give me some balance as I had been pulled about. I knew that my pussy was exposed to anyone at that end of the table.

I opened my eyes and looked down my body. Standing between my legs, leaning over me was Pam. I looked upwards and at my head I could see Jim. I briefly wondered where Steve was then I saw motion at the side of the table. Steve walked up to the table and reached down towards me. I was startled by pain from my breasts. I looked down and saw nipple clamps attached to each nipple, with a chain between them. Gradually the pain reduced and a throbbing sensation replaced it.

As I acclimatised to the sensation I saw Pam lower her head. I felt Pam’s hands on the insides of my thighs. She stroked up and down my thighs. I watched as her head got lower and lower and felt her hands edge closer to my pussy. I closed my eyes and let my head drop back, having decided to revel in the sensations. I felt Pam’s breath on my pussy then her tongue made contact and I’m sure I would have hit the ceiling if I hadn’t hbeen held down on the table.

Pam knew how to give pleasure. She teased me with her fingers and tongue for an eternity. She would slide her fingers between my lips and just inside my slit then replace them with her tongue, dipping inside, then suck my lips into her mouth and nibble on them gently with her teeth.

All of a sudden she moaned with pleasure into my pussy. I lifted my head briefly and behind Pam’s bent over form I could see Steve standing tall. As I watched, he nudged forward and Pam’s face pressed against my pussy. Steve held her hips and fucked Pam as she continued to pleasure my pussy. The different movements and stimulation were alternately frustrating and arousing. I could feel myself reaching my peak then subsiding.

As Steve’s pace increased, Pam lifted her face away from my pussy and rested against the table. Steve seemed to be hitting the right spots.

I realised that Jim had released my hands and I brought them down into a more comfortable position by my sides. As I did so, Jim walked around the table to join Pam and Steve. He moved next Pam then I felt him take hold of my thighs and edge me towards him. As my bum reached the end of the table Jim’s penis made contact with my pussy lips. He edged forwards and the pleasure rolled over me as his penis filled me.

Pam and Steve moved away from the table and over to the sofa. As Jim established his own slow and steady pace with me Steve sat on the sofa and Pam climbed on top of him. Jim released my thighs and used one hand to play with my clit as he slowly and steadily fucked me. The sensations Jim was sending through my body meant that I lost interest in Pam and Steve, although I could hear their bodies slapping together.

I was moaning so loudly I was surprised I could hear anything else. Jim’s staying power was impressive. He would pause every now and then as he got close to cumming. His stimulation of my clit kept me close to my peak.

I suddenly heard Pam scream with pleasure as Steve brought her to orgasm. That seemed to inspire Jim. His pace increased and his moans got louder. Then he thrust his hips one last time and groaned loudly. I immediately linked my ankles behind his back and pulled him tightly to me. He leaned over me with his hands resting on the table. As he twitched inside me, depositing his sperm, he leant down and nibbled on my breasts. That was all I needed to send me over the edge.

I lifted my hips off the table and ground against Jim as my orgasm washed over me. Then I must have blacked out.

The next thing I knew was a conversation going on around me. I can’t remember the details, just the murmur of voices. As I became aware of my situation I realised there were cushions underneath me. I groaned as I opened my eyes. I was now on the sofa but my muscles were aching from the unusual position I had been in on the table. The others were sitting at the table dressed in bath robes. I was just covered by a sheet.

Steve stood up and shakily made his way to me. He lifted my head and shoulders and slid underneath so that he was sitting at the end of the sofa and my head was resting on his thighs. His hands gently stroked my hair and face. He asked if I was okay, to which I could only reply with a smile and a nod. I felt too tired to go to our room just then so we spent the rest of the night in Pam and Jim’s suite.

We also had a lovely breakfast together the next morning and spent a couple of days together over the rest of the holiday. During that time Pam and Jim introduced us to the pleasures of toys and games. It was a time we both enjoyed and benefited from.

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