Written by Paul
30 Dec 2009
The First Time Is The Best Time
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13 minute read
Over the years I have found that there is nothing stranger than life itself. Of the many apparently genuine accounts described on this site some attract cruel criticism for nothing more than poor grammar whilst others could be best described as the work of a frustrated individual or an over active imagination. Either way, let us not forget that this site is a vehicle for our excesses and intended to be fun.
For me the best stories and most convincing are the ones that describe the emotional turmoil before, during and after the event. Some people are no doubt matter of fact about sex, but for us, that first time of offering my woman to another man was a quantum leap from the fantasy pillow talk we had shared on so many occasions. Until you have indulged and experienced this you are in no position to criticize.
I think for us like most it was a progression of events that ultimately brought us to cross the Rubicon. The thrilling pillow talk that begins with, what if? to, why would you want me to? would you really do it? but would you really let me do it? would you want to watch? would you still love me if I did? do you think you could handle it? For us the first time of Lorraine kissing another man at a works night out and us playing up to it later that night in bed was massive. It was the first step to reality.
Also, like most the actual event would probably not have happened unless we were away from the prying eyes, judgement and false morality of our home town. I think it is also true that many of us have taken advantage of the effects of alcohol and the freedom of holidays to fully explore our desires. That was indeed the scenario for us. After the actual event you do crave a degree of reassurance and this site offers the opportunity to share the experience with others and invite comment.
Also, we never realised at the time that we would have a burning desire to share our experience with others and took many months of agonizing and several drafts before we did. You do want to tell but you can hardly be private on holiday then come home and tell the town, can you? Eventually when we did post Dutch courage came to the rescue and it was a drink fueled account seriously lacking in detail. It took from October 2005 to April 2006 to actually put it in writing.
The event took place in Tenerife during a 7 day holiday in October 2005 and was our first of not being roped in with other company. For once we planned time away together and incurred the wrath of one of our friends for not having invited her. We were made to feel more than a little guilty for doing so but soon put it behind us. In hindsight I do think we were secretly hoping for, and preparing for taking that one step further than just the works night out kiss Lorraine had shared with a colleague?
We arrived on the Tuesday on a flight from Glasgow and even before we had booked in struck up a rapport with a couple from Newcastle in reception. They were due to leave on the Friday but we agreed to have a few drinks with them before they left. They were called Tony and Debbie and both thirty years old. They had been going out together for a few years and were really comfortable company. Tony was Jack the lad and a right flirt and used to rile Debbie by chatting up the topless ladies by the pool.
Debbie said she did not mind the play-full antics but Tony usually went too far and showed his dick when he was drunk. Tony used to say, if you have it flaunt it. He boasted more than once that he was well above average. After our afternoon by the pool I suggested to Lorraine that she go topless tomorrow as I would love to see his reaction. We all had a good deal too much to drink that night and Tony did go a bit over the top with some holiday makers. Debbie eventually had enough and ordered him to his room.
On the Wednesday morning the sun was splitting the trees as we prepared to go down to the pool and I noticed Lorraine looking a little anxious. Very unusually, she was sipping from a glass of wine. As she seldom drinks during the day I asked her if she was okay? Lorraine said that she was nervous about going topless but wanted to make me happy and have fun teasing Tony. I told her there was no pressure and not to do it if she was unhappy or uncomfortable with it.
Believe me I want to, said Lorraine with a smile.
Lorraine for some unknown reason lacked confidence at that time in our lives? Lorraine was then 38 years of age and wonderfully proportioned. She is an elegant mover who stands about 5 foot 5 inches tall. Her hair was then dark brown and just longer than shoulder length. Her eyes are hazel and so watery and seductive they make me melt. She is above average pretty and oozes sex appeal.
Her cup size is double D and her nipples enormous when aroused. Her waist is narrow and enhances her figure beautifully. Her bum is fabulous and firm with a gentle wobble when relaxed. Lorraine also has elegant legs that grip you like a vice during missionary. Her pussy was and is the best I have ever had the privilege of entering. It was trimmed to perfection at that time as she planned wearing a bikini on holiday. Her labia swell and engorge with blood immediately when aroused as her pussy lips part and moisten majestically. Her response to sexual arousal is as dramatic as it is instantaneous.
Lorraine seemed unsure what to wear to the pool and seemed to chicken out as she elected to wear an all over blue speedo costume. Debbie and Tony had kept us loungers and we settled down next to them and chatted for a while. Lorraine was the only one drinking as the rest of us seemed to be nursing hang overs that morning. Even so, Tony was soon flirting and teasing the holiday makers as Debbie peeled off her top and released her small breasts. He did not look pleased and a few awkward glances passed between them.
As though for revenge he said to Lorraine, Why are you not topless?
Lorraine replied, in my own time I will be so mind your own business and stop using me to annoy Debbie!
His wings were well clipped as he tried to laugh it off but looked well subdued. It took about half an hour before the tension eased and the conversation was flowing again and as I went to the bar I returned to see Lorraine in the pool. As I approached the lounger she smiled at me as she climbed out of the water and sat beside me. As we talked she removed the straps of her costume from her shoulders and eased it right down to her waist. I was gob smacked. This was her first time ever topless and it was showing on her face as her cheeks were red.
Tony was well impressed as he tried to do that thing of looking but not getting caught doing so. After just a few minutes of liberation Debbie told Tony they were going for a lie down. He did as he was told and followed her to the room.
Lorraine leaned over to me and said, well, did you enjoy that, come to the apartment till I show you something?
As we left the pool Lorraine smiled at me and kept her costume down to her waist as we walked through the entire complex. On the way through the complex we stopped and talked to two young guys in their early twenties who had been on our flight. Lorraine gave each a peck on the cheek as we said goodbye and deliberately allowed her breasts to brush against them as she did so. She was looking really cheeky and excited as we entered the room.
Lorraine looked at me in a really dirty way and said, I really enjoyed showing my body off and deliberately rubbed my nipples against the younger guys and wanted you to pull my costume off and show them my pussy? I am so horny you would not believe it! The thrill of showing off has really got me soaking wet!
Lorraine pulled off her costume and walked to the balcony naked. She did a twirl then walked back inside and sat on the sofa facing the window.
Now! Was all she said as she sat back facing the window and opened her legs.
I took my place between her legs and could not believe how wet she really was? We barely lasted a minute before we came at the same time and went to the room and lay on the bed talking dirty to each other for ages before dropping off for a siesta. Something that did transpire from our pillow talk was of the fantastic thrill we both had from the exhibitionism and that we both would have been happy to go all the way because we were on holiday. We shagged senseless that day and night and seemed to be egging each other on by being dirtier and dirtier.
Next day was the Thursday, and Tony and Debbies last full day as they were flying home on Friday. Lorraine wore a little set to the pool that comprised of a bikini with mini skirt. It was as loud as it was skimpy. The reason for the mini was to hide the damp bikini bottoms as she knew she would be really wet when she went topless again. Tony looked hypnotised but we pretended not to notice. After a day of admiring Lorraines increased confidence and flitateous behaviour round the pool we had barely noticed Debbie becoming legless. About eight that evening Tony had to help her to their room and put her to bed.
We also went to our room and once inside Lorraine put her head under the shower to rinse her hair. There was a knock on the door and I opened it to see Tony standing there in just his shorts. He had come to say his farewells but happily accepted a drink. Lorraine and me went to the room for the duty free and she squeezed her tits as she said to me that she wanted to stay topless and tease him. We both smiled and nodded to each other. Lorraine gave Tony a little kiss on the forehead before she sat next to him on the sofa. In doing so she had practically pushed her naked tits in his face as she leaned forward.
The look on both their faces was now magical as Tony tried to stay composed. Tony went to the toilet at this point and Lorraine said she would turn the heat up on him. Lorraines face was almost bright red by now and the first chance she got she stretched an arm out past Tony to pick a set of keys off his side of the couch. Again in doing so she had brushed past her breasts agaist his arm before leaning further over and literally dropped them in his lap. Tony looked scared and seemed to be freezing.
More drinks, I said and walked to the frige in the kitchen. Lorraine followed me in and quickly stood behind the door and lifted the mini before pulling off the bikini bottoms. As she bent over and bared her bum I almost came as she slipped the bottoms off. All the strange feelings we had never really considered were engulfing our heads. I felt close to vomiting with excitement and sexual tension as to how this was going. I was feeling passion, jealousy, fear, love, betrayal. I just cannot describe it. We went back to the living area as Lorraine sat next to Tony on one sofa and I sat oppositeon the other.
Lorraine was in charge and Tony looked to be wilting. I sat and watched as Lorraine slowly opened her legs and the little mini rode higher. Her well trimmed pussy looked on fire and her labia had totally parted. If he had dared to look down now he would have been able to see Lorraine in all her glory as she sat back and opened her legs really wide as she lifted the mini to allow a full on view. He didn't though. Lorraine sensed she would have to offer a full frontal to get him to look and quickly stood and moved over beside me on the other sofa.
Lorraine was bright red and her breath was faltering as she sat down beside me. She seemed to compose herself for a moment before relaxing and reclining slightly. I watched his face as I knew he must have been able to see Lorraines slit. My heart thumped in my chest as she slowly opened her legs and allowed the mini to ride up. I looked down and could see her pussy was in full view as Tony stuttered and spluttered every word and sip of drink. My head was spinning at the thought of this man looking at my gorgeous womans tits pussy and noticed the enormous tent in his shorts.
It fell silent for a second then Lorraine said, Debbie said you show everyone your cock Tony, Show it to us then?
Bombshell moment! Tony looked to have freaked and initially muttered an excuse but got to his feet and slipped his shorts down. His cock was a massive 9 inches and totally stiff.
Lorraine gasped as she looked at me and said, can I taste his big cock Babes, please let me?
Lorraine had her tongue deep in my mouth as she got to her feet and dropped the mini to the floor. My head was swiming with yes, no, stop, go, as she took the few steps to Tony and pushed him gently back in the sofa.
She stooped forward as he sat back and took his huge prick in her hand before licking his knob, she then glanced at me in a pleading way and said, can I take his cock Babes, inside me?
Lust swept my mind and I gasped out something like, ride him Babes, fuck him hard!
Lorraine kept hold of Tonys cock as she straddled him on the sofa and I bent forward with my cock in my hand to see his massive cock part her swollen lips and slip inside.
Hold my bum Tony, hold my bum, Lorraine said as she lowered her body on him.
Lorraine whimpered like I have never heard before or since as she clenched her bum cheeks and rode him very very quickly to orgasm. A deluge of spunk was gushing from her swollen pussy as he erupted inside. It had literally taken only seconds since his cock had slipped inside but he was trying to ease Lorraine off him and get to his feet. Tony muttered something as he put his shorts on and staggered out the door. The door was still closing as Lorraine in all her glory pushed me back in the sofa and dripped warm spunk all over me as she straddled me.
It was an instant orgasm and massive too as I spunked deep inside her swollen pussy! The whole thing had only taken about 15-20 minutes from start to finish but will always be remembered vividly by us both. We watched Tony and Debbie leave for the airport the next morning before returning to bed for another session.