Thread: Pajama Stories
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Old 11-14-2022, 02:37 PM
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Being an educator and administrator there were many occasions where trips were necessary for conferences, training, renewal of professional status etc which required out of town travel. Many times (to my initial surprise but later found to be somewhat common) these could turn into ‘let your hair down, we’re out of town and who’s going to see these people again’ moments.
Middle school is an age of hormones raging and required conservative dress and role modeling by the adults in such positions. Thus the work place was usually professional and straightforward playing the role to set a good example for the youth we were charged with developing.
One trip in particular involved the other assistant principal on my campus (female) and the two campus counselors (male & female). The four of us were within 10 years of one another in age but with diverse backgrounds.
The men roomed together as did the ladies. Two day conferences usually found you arriving early for first day presentations, checking in at the lunch break to the hotel and checking out the day following the second conference day…(usually ending too late to drive back safely or arrive at a respectable time).
G and I had a room about 3 doors down and across the hall from S & J. G was about 4 years younger than me….maybe 36 and S (other administrator) about 3 years younger than I while J was the youngest at probably 30. All married and all with at least one kid.
J was a little chunky but nothing which detracted from her looks. Think lingering baby fat but her youngest was 2 so she probably owned it now. S was shapely and attractive with a body shape that reflected her desire to keep younger by physical activity. Both had wonderful senses of their place in the world and humor in the workplace and outside of it.
We always discussed the day’s presentation over meals and compared what each of us had taken from the event and how it could apply (if at all) once returning to campus. This was normal for most trips of a similar nature. The night usually ended with a drink or maybe two but nothing wild prior to retiring.
After the last presentation was complete we turned our focus to dinner plans and preparing for departure the following day. This evening we agreed on Tex-Mex as a treat since no really good restaurants with that fare were close to our homes. And of course the traditional margaritas.
I recall the food being excellent and approved by all as well as the deliciousness of the margaritas (on the rocks, not frozen, which was new for me). Having come in separate vehicles, G and I returned to the hotel while J and S returned in theirs after everyone was assured there would be no impairment driving after the alcohol. We had agreed it was probably prudent to go back and prepare for departure the following day and then decide if we had enough time to get together later for a drink or conversation or whatever dependent of the time of night
All went as it normally does and G and I were relaxing after phoning home to share expected arrival times the next day and reviewing the last two days in our room contemplating our final night. We were pretty worn out mentally and we’re happy to go along with any event our colleagues would be up to doing if anything.
The phone in the room rang and it was J asking if it would be ok to just come down to their room and chill since it was the last night and they felt similar to us as to the energy levels. Sounded fine to both G and I so they said to give them about 30 minutes and to dress casually so we could all just relax for awhile.
So I grabbed some jeans from my suitcase and put on comfortable shoes as we waited the requested time to pass before heading that way.
Upon opening the door to their room J said to come in fellas as she walked away toward the bed and motioned to the two chairs set up at its foot, facing the bed. She then went over to the dresser and asked if we could use a Real margarita as a nightcap. J was in a pair of pajamas like Lucy used to wear back when she and Ricky were ready to retire in their separate twin beds back in the day. Baggy full length pants and baggy button down shirt with a collar. We were a little surprised by the outfit and the offer of a drink in the room and not in the usual downstairs bar.
Apparently they had made a stop for tequila and lime and mixer on the way from the restaurant back to the hotel. I won’t lie, it was somewhat exciting to see the chunky J sashaying about acting as hostess. She was about 5’10, 140ish with C+-D- boobs. Neither of us had seen this side of her on previous outings and obviously not at the school.
G declared we would both be delighted to accept her offer.
I obviously appeared to be good as well. Although the material did not lend itself to nipple protrusion, the spacing of the buttons was interesting. Rather wide. She had the top 3 )counting the neck button) undone although it appeared perfectly normal when standing and facing each of us.
With her back to us making margaritas G and I exchanged glances of basically WtF have we stumbled upon. I don’t think either of us had noticed the absence of S until the door to the bathroom opened and she entered running a towel through her damp hair. She was in a pajama ‘set’(?) of baggy shorts and a matching baggy shirt of a dark but thin soft material and buttons down the front As she shook the towel her breasts were swaying and it was obvious she had lost the bra as well. S was 5’7” or so about 115-120 and maybe full C. We both slid into our chairs as we were served our drinks.
J had her drink in hand and sat cross legged on the bed facing us with pillows supporting her from behind. S took her towel back to the shower area and returned with what appeared to be a ‘come hither’ sort of sexy curly frizzy mess on her head. She too sat on the bed and was on her knees with her legs underneath her.
So, what did we think of the conference was the topic of conversation for 10 minutes or so. Suddenly, as if it had just occurred to them at that moment (or possibly planned) S asked if we were ok with them having showered and gotten comfortable before we arrived. Seemed silly to get dressed again and then undressed/dress for bed. Hoped it was ok. G and I were fine with it. Very fine.
We talked, we drank two STRONG margaritas on the rocks and were introduced to our female workmates who had never been thought about as anything other by either of us until this moment.
There were observations of each butt shape both possessed when they went for a fresh drink or bent and retrieved something from the side table pertaining to the programs we had watched.
The giggle and flashes of side boob where button gaps allowed on each woman was exciting and perhaps more so from such an unexpected source.
S eventually ended up sitting on the bed cross legged as well which was teasingly inviting but never clear as to what lay beyond the toned, tanned thighs.
To say I was relieved we were seated and served was an understatement as my cock was vacillating between puffy and full blown rock hard depending on the view and my imagination. Seated in jeans was just fine.
We finally had to retire and promised to share breakfast the next morning prior to departure. No nip views although S had such a thin top it wasn’t hard to envision them as she moved and the bedside table lamp behind her played ‘spotlight’ and the material clung to them.
Nothing was ever suggested as to playing a game or watching a movie or other social interaction. It made both of us conclude they felt comfortable enough to visit and have some drinks as if we were husbands or two other female colleagues. No big deal. We’ll, maybe not for them.
Many a time in interacting with both over the next few years I thought back to that particular evening and what I almost encountered. G and I never spoke of it and neither did J or S. Which makes me further believe it was just a normal event for them.
Surprised the wife with fabulous sex upon my return. What brought that in she asked??
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