Was this weird? Yeah, definitely. Could I get arrested? Probably. I stopped in my tracks in the middle of the busy airport, bag in one hand, and considered for a moment. I managed to switch off from the hustle and bustle of the arrivals lounge in order to think.
At every stage of this trip, I had stopped and turned around to head back. There was no way this was a good idea. I’d start to head back then stop and have the reverse thought process. She’d love it, what a surprise. It would be such a turn on, so unexpected. Then I’d turn to head on towards the journey I’d convinced myself I needed to make.
This battle with anxiety and doubt continued in my head, but somehow I was pressing on, and almost on autopilot, I’d ended up in a Boston taxi heading for the city centre. I watched out of the window and was fascinated by little differences with home. Strange green and yellow tourist buses and a bridge suspended by what looked like wishbones. I was dropped off on the edge of Boston Common and became captivated by a beautiful building with a golden dome called the Massachusetts State House. I was really here. I was really doing this.
From my correspondence with her, the woman I was trying to meet would be taking her folks to the Emerson Colonial Theatre tonight. I had seen her pictures and would have to find her in the crowd. Again, panic set in. No, this was weird, what reaction was I expecting? She was married, we’d only chatted online. Jesus, what was I doing here? I’d seen weirdoes like me in films. This was crazy.
I was staying in a nearby hotel but had wanted to walk in the park for a while to try and convince myself I was right to be doing this. I couldn’t. I went to the hotel and checked in. The performance was at 8 pm, doors at 7:30 pm so I’d need to be around the door from 7:00 pm. I had bought a ticket, way up in the gods, so I could at least clutch this as I waited outside to blend in a little.
The time flew by that afternoon as I sat in my hotel room nervously. I made my way to the theatre for 7:00 pm.
I was the first and only one there apart from staff going in and out. I’d bought myself some tobacco to keep me company, and seemed to be chain smoking. The first people started milling around from 7:15 pm. I had to shuffle to the side more so I didn’t look like I was collecting tickets, and sneakily kept a check on all the people hovering and going in.
At about half-past seven there were quite a few people outside chatting. It was getting harder to see everyone. Just then an elderly lady asked me for a light. I needed to focus, so I reached in my pocket for my lighter whilst still watching at the door. The lady started up a conversation whilst she waited for me. I checked my other pocket but still kept my eyes fixed on the door, I felt it and without looking at her I held it towards her. I think I nearly poked in the eye as she said, “careful sweetie.” I looked at her and realised I had my lighter in her face. I snapped out of my obsessive nature apologised at her, and chatted with her.
“Good luck,” she said as she finished her cigarette and walked into the theatre. It felt a slight relief that after disseminating my story to her she hadn’t accused me of being a freak or a stalker. It was a couple of minutes to 8:00 pm and the last of the punters outside made their way in. I’d missed them. I’d have to wait until the end. Harder to spot with everyone leaving at the same time. Damn.
I turned to head in when I heard a car pull up across the road, its doors frantically opened and the murmur of people who were late emanated. The car doors slammed shut followed by the sound of hurried footsteps crossing the road. I slowly made my way inside the theatre towards the counter, my eyes firmly in front, but my ears listening to the conversation behind me. It was a woman and her parents.
I sneaked a glance in the window of the door and couldn’t believe my luck. Hurriedly heading towards the theatre was an older man and woman, and alongside them, also hurrying but trying at the same time to put the last of her high heels on, it was her. I beamed, but at no point turned around. She was literally metres away from me, and she had no idea she was metres from me. I reached the ticket booth and their voices got louder as they reached it and waited behind me. There was friendly blame being attributed to who had made them late. It sounded like she was the peacekeeper. That made me smile.
I made my way quickly upstairs and leaned over the edge of the balcony so I could look down and see them enter the auditorium. Her they came. I saw her showing her parents to their seats and then sitting alongside them. It was the first time this evening where I could see her without panicking. She wore a really smart black dress, just below knee length, smooth arms on show. She looked so classy, with her little black handbag, she wouldn’t have looked out of place at a high-class awards ceremony.
I became very content, watching her from above, and my worries seemed to wash away. I hadn’t watched the performance. My eyes had been on her the whole time. In truth, I couldn’t tell you what had happened. The interval had been and gone, and because they didn’t leave nor did I. The time flew by, but I was just transfixed on her the whole time.
I seemed to snap out of her hypnotic lure when the audience began to applaud the end of the show. I saw them get ready to leave as people filed out, so made my way downstairs and out of the theatre. I saw the three of them crossing the road towards her car and so ran up the street to a line of taxis. I jumped in the one at the head of the queue.
It was like the films, when I asked the taxi driver to, “follow that car.” What they don’t show you in the films were all the questions he asked me whilst we drove. I made up some bullshit about how the woman in the car’s parents hated me, and that the only way we could hook up was if I waited for them to go home. This seemed to appease him.
Moments later she parked up outside a row of houses and she walked them to their door. Kisses were exchanged and she headed back to her car. I gave the driver his money and headed to her car also. I waited for her to get in before I knocked on the window. She wound it down.
I knew it was corny, but said, “Excuse me, you wouldn’t be able to give me a lift. I’m from out of town?” She didn’t recognise me, and before things turned weird I added, “I’ve come over from Cardiff in the UK, I’m looking for a sexy pen pal of mine so I can say hi.” The look of realisation came upon her face.
Her eyes and mouth opened at the same time. “Terry?”
I smiled, hoping this would put her at ease. Fortunately, it did. She broke into a shocked smile. Thankfully she was receiving me with the intention I had hoped. She couldn’t believe I’d done this on a whim. She was pleased and found it really funny that I was here. She urged me to get in and that we should go for a drink so we could chat. I was so happy. So happy that I was here with her, and that she was happy also.
We stopped at a bar and had a really good chat. I had a couple of beers, but was so jet-lagged that I made them last. Instead, I bought her what she wanted and she was merrily tipsy. I hadn’t laughed so much in a long time. We spoke about what we knew about each other and how this had never been on the cards. She said she was excited for us to have some fun over the few days I was here. I was so relieved. All that worry about how she would receive me was wasted. I should have known her better. She was just as laid back as she was when I’d been emailing with her.
I explained I was jetlagged and would have to call it a night tonight. We left the bar. She had had a few drinks and insisted I drive, rather than her taxi herself home. I explained I hadn’t driven an automatic, but she seemed game for a laugh and said I should experience it. I asked her if I was taking her home. She said yes, but first I should take her for a drive around so that I could enjoy Boston at night.
In the car, I couldn’t keep my eyes off her legs. I placed my hand on her knee just below the hem of her dress. She tensed up, but as I looked at her face, it wasn’t a negative response, more an excited response. I continued with the usual manoeuvre’s inside the vehicle whilst I slowly slid my hand up further, taking the dress up with my hand as I did. I stopped on her thigh, as if to check that she wished me to continue. She slowly parted your legs, and I knew that she wanted this.
As I slid my hand up further I caught the feint and subtle murmurs of enjoyment from her mouth, and from the corner of my eye, I saw her turn to look out of the window. This turned me on, I could feel myself growing in my trousers. We were on the highway in no time. My hand reached her panties and I hooked my fingers inside. She was wet already. She grabbed my hand, placed it on my leg and then managed to wriggle out of her panties without moving from the seat.
She then grabbed my hand and placed it back where it had been. My fingers glided along the folds of her exposed pussy, under the hood, around the clit, circling in a sensual manner. As she began to wriggle gently, I moved my hand to the base of her pussy, where it was wetter. My fingers flicked through her fleshy lips and pressed against her hole. I pressed my finger against her and her pussy literally began to suck my finger in.
Slowly I could feel it disappearing into this warm, wet opening, as she continued to gently move her hips. I began to move my finger in and out, and added a further two fingers. To accommodate them she really pushed down whilst they slowly slid inside her up to my knuckles. At this stage, I was fully erect but was managing to focus on the road.
She groaned as she raised and lowered her hips on to my fingers, fucking herself in the car seat. It wasn’t long before she came, a wonderful sound and feel of a shudder on my hand as she clasped her legs tightly around my hand. Fuck that felt good.
I removed my hand. She grabbed it and licked my fingers. My cock tried to get harder but it just couldn’t. She had devilment in her eyes. She reached over and began to unzip my trousers. I focussed on the road but let out a few curse words as her hand made contact with me because my cock was so desperate for some action.
The noise of my zipper sliding down seemed to be in slow motion and I wriggled in anticipation. Who could have imagined that a sound could be so sensual? Then her fingers slowly reached inside my flies and gently searched for the opening in my boxers. Once she found it and reached inside, my cock almost jumped to attention, now it was free. Here I was, driving down the highway to who knows where, my cock fully erect sticking out of my trousers, whilst a beautiful woman gazed down at it with intent.
My eyes didn’t leave the road for a second but my mind was completely on the goings on inside the car. I could see her head slowly move above my cock. There was a bit of precum on the head of it and I felt her tongue stretching down and licking it off in one accurate movement, like a fine paintbrush. This was so teasing, but fortunately for me, I was teased no more. In a slow movement, I felt my cock entering her mouth. It was hot and wet.
Her lips clasped around my cock and I could feel her begin to suck. She was sucking the head of my cock with her wet tongue pressing against it. She then proceeded to lower her head slowly, taking in more of it. I bit my lip, then I swore, in disbelief at how good this felt. What was incredible, is that she kept going down, my cock had never been this far inside a woman’s mouth before and fuck it felt good. I felt like cumming.
Her head pressed all the way down to the entrance on my trousers. She had my entire cock in her mouth. She sucked, I mean she really sucked the whole length. Then she lifted her head slowly, leaving a trail of saliva on my cock as she raised up it, but before she came off at the top, she plunged her head back down, all the time sucking, all the time her tongue sliding along my length. She built up some speed, always down the entire length. I was going to cum.
My eyes were on the road, but only just. I couldn’t resist, I took my hand and pressed it on the back of her head, forcing her down as far as it was possible to go. “I’m gonna cum!” I shouted as I held her head firmly, she continued to suck as hard as she could, I felt the orgasm building up inside me, there was no stopping now. I released my load relentlessly in her mouth, my cock pulsating as load after load shot down her throat. I think I momentarily closed my eyes. I could her swallowing as I unloaded and she never stopped sucking.
Even once my seed was spent, and I know there was a lot of cum because I felt each load blasting into her mouth, she stayed on my cock. Right to the base. She waited until every last drop was gone, and as I removed my hand, she slowly glided her lips up my cock and popped off the top taking every dribble of cum with her. “Mmmmmm,” she said as she sat back in her seat. She smiled and looked out of her window at the city lights in the distance in happy contemplation. “What do you want to do next?”
Source: reddit.com/r/eroticliterature/comments/p6m0ez/trip_on_a_whim