Virgin's First Holiday Experience

The first time I ever went on holiday without my Mum and Dad was back in the summer of 1978 soon after I turned 19.

Trudy, my good friend and I had for some time planned and eventually convinced our parents into letting us have our first unescorted holiday together in Spain. It would be my first taste of freedom. Unlike at home we would be free to go out to all hours without curfew rather than being at home by twelve under my parents house rules. I even decided I would travel as a single, available girl, just in case something wild happened. No boyfriend at home, no guilty feelings if I met someone who met my fancy. Of course I dreamed for months that perhaps Prince Charming would sweep me off my feet. What would I do?

Living in the outskirts of London, like most young women I enjoyed going out, eating, drinking, dancing and flirting on weekends. But our holiday would be without all the challenges at home. We wouldn't have friends watching, chaperoning, and no parents waiting at home. For my first time I would be completely free to do as I pleased as a young adult woman.

I was a rather strait-laced simple, naive small town girl going away on her first holiday. And, I was still a virgin too. But I knew it could and would happen sooner or later.

The closest I had ever been to doing it, was to let a boyfriend get his hand inside my knickers and stroke my pussy, but that was only after we had been dating for several months! I have to admit, there were plenty of boys interested in me though. But this week I would be on vacation with plans to drink, dance, flirt and tease. No restrictions.

My best friend Trudy joked excitedly on the flight southbound, engines roaring in the background as we discussed opportunity. "Who knows, it might happen if I meet the right guy." Trudy surprised me though. "You know I'm on the pill now since last month."

I was caught off guard mesmerized wondering if this was all intentional. Was Trudy planning to finally do it. At that moment I questioned her, "Really Trudy, do you think I should maybe have..... perhaps gone to my doctor as well?"

"Well maybe girl. Don't you think, sooner or later you're not going to tell a hot guy 'please not tonight.' I mean don't you think sooner or later you'll let a guy get lucky?"

"I guess, maybe." But naively I didn't plan for it avoiding the whole question in the months leading up to the holiday.

"Think about it. You know going all the way will happen. Maybe you'll have sex while on holiday." Trudy suggested. But wow. "And you know Anja there are condoms too. I guess finding some would be smart." Trudy suggested.

"Yeah, I might get some from the hotel pharmacy." I answered.

"But honestly, don't you think about it happening with your 'Prince Charming' don't you?" She asked.

"I guess so." I answered.

"Well besides, you know it's gonna happen sooner or later." Trudy suggested.

"True, But I'm not out looking for it to happen." I argued innocently.

"Honestly Anja. We're alone on holiday. My mum suggested it might be smart to see a doctor when I told her we were planning a holiday in Spain. Trudy admitted.

"Really!" I answered.

"Yes, She told me. She had travelled with her best friend when my age and things happened. 'What things happened' I asked my mum. Mum smiled and told me.

"Trudy, put it this way..... beautiful naïve virgins don't stay virgins forever."

"Jeez Mum?" I answered. She whispered back, "Trudy things happen. You're not going to be a virgin forever. You planned this holiday and I am sure there will be interest. You need to see your doctor about the pill, all right!" "Ok Mum! I told her.

I now realized figuring Trudy wasn't at all against doing it for her first time while on holiday. Just like her mum. On the other hand that conversation never occurred between me and my mum. So I was traveling without having considered it or preparing myself for it happening.

"Well Trudy do you want to do it while on holiday?" I asked.

"Probably. I'm going to have sex sooner or later when I meet a nice guy. I'm ready to let it happen. So I think it might finally happen this week. What about you?" She asked.

"I dunno. I mean most guys our age want it so I guess it could happen." I confided.

"Then where going have an interesting holiday?" She asked.

"I guess, maybe, we'll see, I dunno." I answered feeling a moistness in my panties just from talking 'bout doing it.

We arrived Thursday just after noon. After getting settled in, we had dinner before going out for an evening walk along the beach boardwalk. Two guys, came up and started chatting us up. I wasn't quite ready to be picked up just like that. Despite their offer to go for drinks we decided before dinner we would call it an early night being a bit tired from the early morning travel.

Given the discussions onboard I figured I likely would be approached by guys looking for action while on holiday. Unlike in my normal home routine everything here seemed to revolve around singles hooking up while away on holiday. I then decided it wise to pop into the resort shop and discreetly I bought a box of condoms like discussed just in case something did happen.

The next morning we had breakfast before beach time just as planned. I was a bit surprised when I walked into the hotel lobby that afternoon and found Trudy talking to the same two men we met the night before.

Trudy told me a few moments later that it turned out they were actually staying at the same resort as us. It would be their last night and they suggested we join them for some drinks later. The way she looked at me told me that she was interested. So I agreed we could meet them for a double date after dinner at around eight.

It was Friday and after a hot day on the beach I got myself ready for a night of partying. It was quite warm so I chose a light short summer skirt and a light button down blouse. With my pumps, makeup, jewelry, and little undies I felt quite good about myself. I was dressed perfectly for a night of hopefully free drinks from our dates. I was good and prepared for some serious partying.

After dinner, as planned, we headed to the hotel bar. Trudy and I found a Table, had a cocktail together before the men joined us. When they finally arrived I quickly knew Trudy was enjoying, focused on Tony. She had quite obviously clicked with him. They were a little older than us both 23. But we were now 19. Old enough to travel, drink and go out and party as young adults.

It definitely crossed my mind. Was Trudy considering having sex with Tony? He was the better looking of the two. Somehow in my dreams I had always got the better looking man, so the tables were turned. I felt that I'd been left with the consolation prize Dave, but that wasn't too bad. He wasn't bad looking and was reasonably amusing. He asked me what I did for work, my career plans and what I thought of the hotel, the resort. I frowned and explained they'd messed our room around. In what way he asked. "Well it's our first holiday without family. We booked a twin, but they gave us two small single rooms instead."

"Isn't that for some perspectives better, more private?" he asked.

"Girls like time together to gossip and such. Anyway at least they're connecting" I replied, "But they're poky little rooms stuck right up on the top floor."

We had another drink in the hotel bar and then Tony suggested a walk down the boardwalk to a club. Tony and Trudy led the way with their arms round each other, and Dave and I followed. We chatted, but likely to Dave's disappointment I kept my distance. He mentioned I was very beautiful and complimented my cute outfit but as always with new dates I was a little shy and resistant.

After several more drinks and playful dancing at the club I was getting a little tipsy. It was approaching closing time so we all agreed to start walking back for another drink at the hotel bar. By now I'd mellowed a bit (probably a lot because of all the drinks) and I didn't resist Dave putting his arm round me.

Trudy and Tony were in front leading the way. The stopped and started to kiss. "Look at them!" I said to Dave. His only reply was to pull me tight and kiss me too. I didn't resist and in fact after a little I felt a familiar moistening in my knickers that sometimes happened when kissing. Some people were approaching, so we briefly stopped. They passed before Dave pulled me close kissing me again, I could feel his stiffness against my leg.

Eventually we continued back to the hotel. We had that drink in the hotel bar with Trudy deep in conversation with Tony. She was smiling and laughing, obviously very taken with him. Soon afterwards went together to the loo. She told me Tony wanted to see her room she'd been grumbling about. But she giggled nervously telling me she didn't want to go to her room alone with Tony and would only go upstairs if I came along too.

I shrugged and said "Well ok" wondering but not asking if she was considering alone time with Tony. So off we went holding hands.

The lads looked at our rooms. Both said the adjoining rooms were OK and not near as bad as we had made out with nice views of the pool below. With the four of us together in my room Tony took Trudy by the hand and said "Common Trudy, let's take another look at your room." She looked back at me innocently nervous then he pulled her through the connecting door and shut it behind her separating ourselves. Suddenly we were two couples alone in our rooms with our dates.

I was a little hesitant being alone with Dave in my room but Trudy was close by, even if she was alone with Tony in her room. I guess with nowhere else to go I innocently sat on my bed and Dave quickly followed. Rather reluctantly, I was there and of course he pulled me in for a kiss. His hands wrapped me tight pulling me close.

Soon, not surprisingly with a kiss his hands found my breasts. I let him do that, it was actually very nice. Then he caught me a little by surprise progressively undoing the buttons on my blouse one by one as we kissed. I protested lightly as he released my bra clasp, but it did feel nice when his warm hands began fondling my perk little titties. I guess I didn't really try too hard to stop him. This guy was putting all the moves on and it didn't help that we were alone in my room after a night of heavy drinking.

The next, rather predictable move was his hand on the inside of my bare knee ready for the predictable journey up my leg. I had no intention of letting him do that. We had just met and I didn't even know him. I took hold of his wrist and held his hand where it was. I was a little challenged being alone with a man in my room. Obviously I was with a suitor who wanted to play. Persistently he kept trying. We kissed as he stroked my boobs wth one hand and the inside of my leg with the other trying to get his hand up my skirt. But I was strong not letting him get near my knickers.

Eventually, tired with this wrestling match I used the Trudy excuse to slow things down. "We need to check on Trudy."

"Oh I'm quite sure they're busy." Dave answered unapologetically. "We should leave them be." With that he again kissed me trying to get his hand further up my skirt.

Since I started dating I had gotten used to, or should I say accustomed to sexual aggressiveness. I sometimes even enjoyed the chase. It was always a bit of a challenge though. It seemed most men were more interested in seeing how far I would let them go rather than me as a person. There always seemed to be that male ultimate desire present. It was a repeating game of progression. Always, of course, kissing first before pressing on. Then fondling my boobs before going for more. When wearing pants the chase was more controllable, easier to stroke my legs even my pussy but without any way to get to my knickers. And a side zipper made it clear things would not progress. If I wore a skirt or dress on my third or fourth date getting to my knickers would always be the objective. Dates would push hoping to score and I would chose how far or successful they might be getting. Honestly, I wasn't at all naive and innocent having willingly stroked several dates cock's while getting my pussy stroked. I had given hand-jobs even getting spunk on my boobs more than once. I had even given blow-jobs several times but had never let a date fuck me. Regardless, I was a 19 year old virgin on holiday having been mostly a good girl resisting the temptation of letting a suitor have his way.

I separated myself from Dave quickly standing then straightened myself out. I pulled my skirt back into place and rebuttoned my blouse without reclasping my brassiere. I was pretty well proper again.

Before looking to check in on Trudy I glanced back at an obviously frustrated Dave while approaching the connecting door. Slowly, quietly, I opening it not really considering what I might find. I was caught off guard. Honestly I was totally amazed and dumbstruck. Trudy lay on her bed, on her back, her eyes shut tight, her mouth open in a perfect O. Her skirt on the floor. Her knickers hanging from her ankle, her knees raised high outside his hips. Tony was on top nailing her. His bare backside rising, then falling, rising then falling. Tony was having his way with Trudy. She had given in to temptation, no longer saying "not tonight" to a suitor. She was getting laid on our second night on holiday!

I stood by the door watching the show in a bewildered awe. I was a little amazed that my friend Trudy had so quickly chosen to do it. Okay, I knew she had gotten on the pill before going on holiday. But jeez, that didn't take too long. I guess she just wanted to, needed to cross that line.

Frozen in place I watching amazed. Dave, from behind gently put his hands on my hips and whispered "Let's leave them be." He reached around me quietly shutting the door separating the rooms once again. "Quite the show Anja. Don't you think?"

I nodded knowing we were alone again. Dave spun me around, pulled me tight and kissed me confidently. Honestly, I was lost suddenly realizing my holiday was not going to be what I had thought. Totally in a numb fog having seen my best friend Trudy fucking, I figured Dave, was surely hoping to get from me what Tony was enjoying with Trudy.

I found myself circling back to my bed to again play that 'will she or won't she' game. He was quickly aggressively going for it. First kissing, which I enjoy, before making his move undoing the buttons on my blouse again, one by one. Quickly claiming what he already had won.

Knowing the tempting game I didn't stop the chase. Not yet. I found myself sitting on the bed again with an obvious interested suitor. His warm hands quickly found my boobs inside my blouse, shall I admit, felt nice once again. After a bit kissing his hand found my bare leg just above my knee. Having seen Trudy doing it I was thinking about sex questioning what would soon follow with my raised excitement. Honestly, after the Trudy and Tony sex show and being aggressively man-handled by Dave I was a little, maybe not a little. I was quite warm.

As always when alone with a man I had to make my decision just how far I would let him go. Like before on dates with aggressive boys I was heated up and more than a little wet. But that didn't mean I would let my suitor have his way. But after more long sensual kisses. I guess. I started to melt, weaken, give in just a little. I consciously, shall I say, let Dave push my knees slightly apart, just a little. With our next long deep kiss Dave's hand slowly worked up along the inside of my leg. I knew what he wanted. Honestly, not the first horny male alone with me wanting to get to my knickers. But this time, unlike earlier, I didn't stop him from moving further up my skirt. He was the third boy successfully getting his hand to my knickers, reaching, finding what he wanted, pussy.

Without hesitation Dave started stroking my knickers enjoying my innocent cunt. I didn't resist too much as things continued heating up. Oh we kissed. I didn't stop him. I was being seduced and I knew it. He then brazenly took the next step tugging at my knickers. He knew what he wanted, I knew it too. Decision time had arrived.

The question remained, would I deliver and be a willing cunt just like Trudy? Would Dave get lucky? I was on holiday and sex was in the air. I caved not stopping him. I raised my bottom letting him pull my knickers down.

Now deep in the chase game I was in new territory. I was alone in my room with an aggressive male. I soon discovered he conveniently didn't bother to wear underwear tonight. No doubt hoping to get lucky with some willing tart, me. He unzipped then pushed his trousers lower exposing his stiff cock. After losing his pants he brought my right hand to his cock. I did my part stroking it. Not the first cock I stroked having done that several times with dates.

After several minutes of more passionate kissing, fondling and such. He was teasing and fingering my pussy while I stroked his big stiff cock, making it even harder, bigger preparing him for the next phase. I was really wet and honestly super excited. Was I caving like a sex starved slut? I asked myself again, Would I suck it or even maybe let him go all the way? I didn't answer knowing I would have to decide soon. It would be either say "no" or let him have his way.

Dave continued working me, bringing me slowly closer to what he wanted. It wasn't long before Dave had me on my back just like Trudy. He moved into position with his body pressing against me. The chance to say "no" had passed. I would let him have his way.

I had never experienced a male on top before. Dave was ready to do me and honestly, I was waiting for it. With my blouse open, my skirt loose, my knickers off and Dave between my knees I realized that soon, just like Trudy I would be getting fucked.

I considered the box of condoms in my purse, "Dave, there's a safe in my purse, please." I asked, but either he didn't listen or he was just ignoring the ask.

Dave continued. Being persistent he lifted my knees and pushed them apart. I understood what he was doing. My legs would need to be spread wide if it was going to happen. He was doing his thing working me into position. He lifted my raised knees around his waist with his hardness suddenly there touching, tracing, teasing my pussy lips. It was intense. He was ready, eager for the fuck.

I had enough nervousness and concern to repeat, "Dave, please, we need to grab the condom." I realized he was focused on one thing. Getting his cock into me. And seriously, grabbing protection apparently wasn't in his plans. That was quite obvious now. Like his friend with Trudy he was wanting and ready to have his bare cock somewhere wet and warm, meaning in my cunt.

Immediately after asking him to use protection he began introducing his cock to my innocent cunt. I nervously knew this was going to be it. My first time. There at my moist excited lips he moved his cock along my sex. My eyes shut I waited with his cock there. I moaned softly as I felt his hardness there ready to begin its journey.

I thought to myself, the fucking condom's in my purse! But I couldn't find the way to mention it again. The whole seduction chase was so deliberate with his cock right there. Now that it was about to happen I wanted to ask again but I only whispered, "Please go slow, be gentle. You're my first." Was all I could get out.

"Really, an innocent virgin? No way Anja! I figured a gorgeous sexy broad like you would be experienced." Then after a pause he added. "I'm gonna really enjoy this!"

I blinked then nodded looking up into his eyes. I had been successfully captured and was about to experience sex for the first time.

After a short pause he whispered. "Listen Anja we're doing it no condom. Okay! Its so much better." He answered as he started working his baby maker into me. I couldn't speak, I just nodded. All I knew was I was getting fucked. He was going for it and I was overwhelmed.