My Trip Into Town

I love sunny days and for my venture into town I decided to wear a pair of dress shorts mainly because they have pockets and a button up shirt in my attempt to look presentable.
I rarely wear underwear and today was no different as I like to let my tackle breath as well as giving easy access to any interested parties. I waited until the morning rush had died down so the 20 minute bus ride wouldn’t be too busy and as I waited at the stop there was another woman waiting and as I checked her out I figured if I could sit opposite her it would make for nice eye candy for the short trip.
We never made eye contact as we waited for the bus as I’ve found from experience that I I check them out too much and then sit opposite them on the bus they get a bit nervous thinking I’m some kind of pervert so I purposely looked the other way.

The bus arrived and my plan was working and I was able to get a seat directly opposite the lady who was probably in her mid to late 20’s and had a shortish skirt on and a colourful blouse. She sat with her knees together as I would expect but due to the shortness of her tight skirt unbeknown to her I was able to see right up her thighs and got a perfect glimpse of her white gusset, this would certainly make the trip more interesting as she had no idea I was looking as she had her head buried in her phone.
Now bus rides are never smooth and with every bump her legs wobbled giving me an even better view of her little white pa ties and not once did she look up, it was like I wasn’t there which is just how I like it.
As luck would have it she was getting off at my stop so I figured she must work in town and as I let her off first she did give me a warm “Thank you” smile.

I went off and it took me about an hour or so to complete my errands and then I popped into the pub for a beer and a burger and was their only customer for quite a while as it hadn’t got to lunchtime just yet.
I sat at the bar and the only bartender was the landlady who I had known for years and although nothing to look at she did have a good personality and we always had a good catch up whenever we met.
I didn’t want to go home just yet as I found the afternoon school buses lent themselves to possible opportunities so I figured I would have a walk around town to see what’s new.
I saw there was a new clothing store opened and I always like to browse so I went in to look around, it wasn’t a big sore by any means and at this point it looked like I was the only customer, “Can I help you sir?, are you looking for anything in particular?” the sales assistant said in a soft polite voice and as I turned around I saw it was the girl on the bus, “Oh hello again” I said with a smile and she instantly recognized me, “Oh hi, you’re the guy on the bus this morning” she replied and we instantly struck up a rapport.
“First day and I’m late” she said with a giggle, “And now the boss has gone out and left me to it” she added and I got the impression she was glad to have a customer.

She looked me up and down and even if my shirt was half undone I still think I looked presentable, “I see you’re a casual dresser sir, what can I interest you in today? We have a great range in casual shorts and trousers sir, what size are you?” she said getting into her light sales pitch and I told her that it had been a while since I brought clothing and had no idea of my sizes.
She was very well presented in her colourful top and tight short skirt and I have to say she did have nice tanned legs and from the bus ride I even knew what colour panties she had on, “Don’t worry about that sir, that’s why I carry a tape measure” she said with a smile as she ushered me to the back of the shop and as I followed her I could see she had a nice, shapely arse and the thought of her measuring me did give me a slight bulge which in a way I hoped she’d notice but then again I hoped she didn’t.

My button front shirt was untucked so hopefully she wouldn’t notice my impending erection but as we got to a rather spacious fitting room she pulled up a little stool, “Right sir, let’s have a look at you” she said looking right at my dress shorts clearly seeing my offending bulge and what made it worse was I could see right down her blouse at her matching white bra which seemed to be struggling to contain her nice little titties.
“If you want sir I can take all your measurements and set up a customer file for future reference” she said as she again looked me up and down and it was clear she had noticed my growing boner although she didn’t make any reference to it, “Yes Kim, that’ll be good if you have time” I replied and I knew her name from her name badge, “Well it’s not like I’m rushed off my feet sir” she replied with a giggle.

She got up and got a new customer form to fill out and on her return sat back down with clipboard in hand. She stood up and reached around my neck and got so close I could smell her perfume which I must say wasn’t helping my erection issues, “Good” she said making a note of the size, “Shall I open my shirt so you can do my chest?” I asked and she smiled and nodded her head as I undid the remaining buttons exposing my chest causing Kim to take a deep intake of breath but what’s more things were about to get interesting as my bulge was now clearly visible. As she reached around me I felt her fingers linger around my nipples and I have to say she had a nice soft touch, she eventually took the measurement and recorded it.

With only my waist and inside leg to do Kim seemed a bit hesitant as she was confronted with my shorts which clearly showed my aroused state, she reached around my waist with the tape and I have to say her head got dangerously close to my upright bulge and being a bit flustered by having this in her face she dropped the tape and I understood she was trying to be professional and probably wasn’t used to having an older man with a boner in her face. She reached down and picked up the tape and there was definite contact which we both chose to ignore. She finally got herself together and got my waist measurement and recorded it.

I looked down at her as she contemplated measuring my inside leg and with my shorts being baggy there was plenty of room if she dared go there and as she held one end of the tape in her fingers she looked up at me to see if I was going to help and quickly realized that I wasn’t, “Um, apologies for any inappropriate touching sir” she said as she ran the top of the tape up the leg of my shorts and there was no mistaking her accidental touching of my balls, what was interesting was that as she ran the tape down my leg to my ankle her head once again brushed my bulge and I don’t think it was my imagination when I felt her fingers wiggle across my balls and she lingered there far too long and I even felt my cock pulse against her face.
Finally she came back down and recorded the measurement, “I think I best check the other leg sir, you’d be surprised at how many people have legs that are different sizes” she said with a giggle as she repeated the process with the other leg but this time there was much more prominent touching up inside the leg of my shorts and she lingered for a lot longer.
She happily announced that both my legs were equal which was pleasing to know although I was never in doubt and I now wondered what he next step would be, “I noticed that you’re not wearing any underwear sir, is that normal for you?” she asked, “The reason I ask is that we have some great deals on boxer briefs if you’re interested although judging by what I’m seeing we would need to get the sizing right to ensure maximum comfort” she said as she looked up at me, “Well to be honest Kim I don’t normally wear underwear but I would be interested for you to get the right sizing” I replied with a smile wondering how she was going to obtain the information.

My cock was rock hard now and all through the measuring process I’d had my eyes down the front of her blouse which only came to a halt as she got up to check on a customer that came into the store but she soon returned with a pack of boxer briefs in hand. “Maybe you can try these sir as it will give me a starting point if they don’t fit correctly” she said handing me a pair of white, “Shall I leave you to try them on sir or do you want me to wait?” she asked and gave me a cheeky smile when I suggested she take a seat and wait as I could then get her professional opinion. She took a deep intake of breath as I undid my shorts and as they slipped to the floor my cock sprung up standing loud and proud and I saw Kim’s eyes widened as she finally saw what I’d been teasing her with, “Wow sir, you might have problems getting all that in” she said with a giggle and as luck would have it they were made of soft stretchy material and although they made my boner visible they did actually cover me, “Do you mind if I check the fit for you sir?” she asked and I told her to go ahead as she was the expert.

She reached out and cupped my balls giving them a gentle squeeze in fact she was almost fondling them and not quickly either, “Hmm, they seem to fit ok here sir” she said and then keeping her hand on my balls she reached out the other hand and placed it firmly on the solid shaft of my cock and wrapped her fingers around it giving it a gentle squeeze. I was amazed at how springy the material was and there was room for movement as well making them probably the most comfortable briefs I’d ever worn.
“Turn around for me” she said removing her hands so I spun around and straight away she replaced her hand between my legs again grabbing hold of my nuts and with the other hand she fondled and squeezed my arse cheeks before running her finger up and down my crack, damn it her hands were touching all the right places.
She spun me around again to double check the front again and grabbed hold of my cock, “How do they feel sir, definitely room for movement and I think they hold your testicles rather snug too” she said certainly getting her money’s worth.

“And look sir, there’s a little button at the front so if nature calls it’s easy to release yourself” she said putting on her best salesman’s voice and then easily undid the button and reached inside and pulling my rigid boner out in front of her face, “You see sir, even with an erection it can easily be released” she added as she wrapped her fingers around the shaft and instinctively pulled the skin back to expose my swollen head.
“Oooh sir, I think they are definitely you sir” she said softly and I could see in her eyes that she wanted to suck it so I subconsciously eased myself forward and she wrapped her hand around my arse and helped pull me closer, “I shouldn’t be doing this sir” she sighed softly as she wrapped her lips around the helmet and I could feel the suction she was creating.

Oh it did feel good and while she had to keep an ear open for customers or her boss I wanted to take full advantage of the opportunity and started to gently fuck her face forcing my cock further into her mouth until I felt the tightness of her throat, she was going at me hard and with her hand still massaging my balls hidden tight into the soft fabric of my briefs I knew I wasn’t going to be long in finishing. She started to suck harder and as I felt my cock starting to pulsate shooting my hot creamy load deep into her mouth. “Mmm yes sir, so nice” she murmured as she sucked the last drops out of me and my cock started to soften. After she was done it was quite easy to poke my cock back inside the briefs and she did the button back up saying how nice I looked, “Slip your shorts on sir and nobody will ever know” she said softly and it looked like I’d got myself a freebie. “Just need to take down your personal details sir if you don’t mind” she said as we walked back out to the counter.
She asked my name and address and then said, “OMG Frank, I live 3 doors down from you” which explains why we were both at the same bus stop, she took my mobile number and told me she would set up an account for me which I thought was nice as it was a pretty decent shop and had nice clothes and staff!!

“At least I won’t have far to come if I need to check any measurements Frank” she said with a smile making me wonder what measurement she would need to double check. I liked Kim and she gave a great blow job albeit a bit rushed and it made me wonder how good she would be in an unhurried and private setting plus I wouldn’t mind taking a closer look up that tight skirt of hers. “Maybe I’ll bring a few pairs of boxers around Frank for a private fitting” she said with a cheeky grin and I told her I wouldn’t mind her doing that and I’d be pleased to see her and as a few customers came in I felt it best to leave her to get on with her work, she handed me a note with her number on it so I knew she was interested. To be honest the boxer briefs felt comfortable and I hardly knew I was wearing them making me think that worst case scenario they would be great to lounge around the house.

As I walked through town to the bus stop I found another advantage of the super cool boxer briefs was that even with an erection it kept my cock close to my body so any boner wouldn’t become visible, a total win/win situation. As I got to the bus stop there were half a dozen or so students from the local girls’ school and I knew that when the bus came there wouldn’t be much room so again I was thankful for my new underwear.
As the bus arrived I let the students get on first as it’s more fun squeezing past them with the occasional “Sorry love” as my hands brushed past them and every now and again I’ll get a smile and an “Its ok” from them, today was no different as I tried to make my way to the center of the bus by the stairs as it will often lead to a few sneaky peaks as girls went up or came down.
As usual when I catch this bus we were packed in like sardines and I was sandwiched between two young girls which is where the benefit of my new briefs came in because I was unavoidably pressing up against one girl and the one behind me was pressing hard against my arse and with every bump the bus made accidental contact was made and I could feel my boner pressing against the girl in front who was none the wiser thinking it was purely accidental.

We had gone about 2 or 3 stops and with more people getting on than getting off we became more squashed together and then her girl in front put her hand behind her to figure out what was pressing against her arse and I felt her fingers touching against my boner but she just continued looking ahead like nothing was wrong. We then approached another stop and quite a few girls started coming down the stairs and while I tried to hold my position for as long as possible and I did get a good, perverted peek up a few skirts I was soon separated from the girl who was once in front of me.

The bus was starting to empty now and I doubted I would get another opportunity to get as close to the girl who I noticed had sat down near the front of the bus however as we got closer to the end of my journey I was able to stand right next to where she was sitting and with my shirt still untucked I did notice that my shorts were at the same level as her head and I did notice her glance a couple of times and as I had to squeeze closer to her as someone passed me my boner got very close to her head in fact the top of my thigh was touching her shoulder. Of course I apologized for the accidental brush and she looked up at me, “Oh it’s ok” she said softly like she actually enjoyed me brushing against her, there were still 2 or 3 stops to go so maybe all is not lost.
It was when the girl sitting inside from her wanted to get off and not only did the original girl have to raise herself up the bus jolted as I tried to make way and I ended up with my crotch basically in her face and I defiantly felt her pushing into my cock and because it was such a tight squeeze we were like that for far too long and by the time the girl had got past the poor original girl had her face still pressing against my boner, god forbid what would have happened if I wasn’t wearing my new briefs, I think my cock would have poked her eye out or something.
I held on to the rail on the ceiling of the bus which in turn raised my shirt up filling exposing my arousal which even in my new briefs was visible and the girl sitting seemed to take full advantage of the situation and had turned her head almost mesmerized by the clear evidence that was right in front of her eyes and knowing she was looking and about a couple of inches away seemed to make my cock even harder.
My stop was fast approaching and imagine my surprise when the girl also got up to get off the bus.

To Be Continued…
Published by britguy
3 years ago
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