It had been 5 months or so since my last random day off from work lead to me meeting a complete stranger and being his cute little sissy by the end of the night. I was kinda busy at work when I got a text to my phone that said "hello" from a number that was not saved in my phone. I thought it was a wrong number and ignored it and later had deleted text without replying . Three days later another text from the same number "hello ? " I promptly replied " I think you have the wrong number" and set my phone down to read for a bit . Right before bed i checked my phone and had a reply that said " this is Donald's wife . I was instantly nervous because when Don and I parted ways last time I didn't know if his wife knew anything about his like for young men and I didn't want to let anything out that she didn't know. We talked for a bit and she told me she knew all about us hooking up and that she was totally OK with it . She was actually texting to see if I would like to join them for a birthday dinner at their place for his 50th birthday. I had 6 weeks to plan and could get the night off so I agreed and she said " we would work out the details " .
Two weeks later I got a text from her and during some back and forth small talk she had said to dress nice and asked if I wanted to meet up to go shopping . That Saturday we went to the local mall and tried on some clothes she had picked out for me and she had tried on a few short flirty dresses asking my opinion . I had bought a new outfit pants , nice shirt and new shoes . She had purchased a very short dress that showed her nice mature figure just enough cleavage and short enough to cover her ass but give you a peak of her pink lace panties when she walked . Over the next 4 weeks we had exchanged some texts some a little flirty but nothing over the top the whole time keeping the birthday surprise hush hush.
The night of dons birthday dinner was here and I had spent all day getting ready. Fresh hair cut , shaved smooth and very well manscaped. I put on my new outfit and headed out the door . I arrived at 4:30 as planned when I pulled into the driveway she called to me from the door telling me to pull into the open garage bay and close the garage door. I did as she requested and walked to the door that goes into the house from inside the garage. On the landing in front of the door was a small gift bag with a balloon that had my name on it . I opened the bag and inside was a pair of sexy teel lace panties , a pair of sheer black thigh high stockings and a note that said to put them on under my cloths and come in . I did as told and when I got inside she came over and gave me a hug running her hand over my slacks to feel the panty lines . Realizing I followed her instructions she slapped me on the ass loud enough to echo through the kitchen and said " good boy" . Standing there shooting the breeze she asked if I wanted a drink and I answered with " just some whiskey on ice is fine " and she giggled while saying" that's a man's drink my dear" . She walked back in with 2 tall drinks that had bright straws and umbrellas and finished those in 30 min or so just in time for Don to get home from work .
Don walked in looked totally surprised to see me but happy I was there came over shook my hand and gave his wife a hug and kiss . He asked what was for dinner and she said it was almost done and that we should go have a seat in the dining room. We all sat down and enjoyed a few drinks and conversation over an amazing lasagna and salad . She excused herself from the table to clean up and we talked sports and how we should catch a Celtics game . I gotta admit pretty hard to act normal and talk about man stuff while wearing nylons and panties lol .
We all headed downstairs to play some pool and chat they had some music going over all just great time . Don and myself play pretty well but his wife will rely on her distraction tactics to win . They were playing a game and as she leaned over the table giving him a nice view down the top of her dress I could now see half of her ass as she was bent over in front of me and noticed we had matching panties and stockings on . We had been shooting pool for a few hours now had a few drinks and taken a few shots when don jokingly made the comment " good thing your not as distracting as she is I wouldn't win a single game " but all night I had been adjusting my soft lace panties while he wasn't looking and he had no idea.
Don had a pretty good buzz going and had told his wife that if he won the next game they would go to Daytona for vacation to go to the Nascar race but if I won they could go to Vegas to gamble like she wanted she quickly agreed . Just after he broke she started her tactics showing her ass bending over the table rubbing on him even grabbing his cock , he messed up and put the 8 ball in out of turn losing . He right away said it didn't count and we were going to play again this time she couldn't interfere. While he was racking she asked me to give her a hand getting stuff for drinks from the fridge. I headed towards the kitchen when she whispered come here and had me follow her to their bedroom . She pulled from under the bed a short schoolgirl skirt and some size 11 heels and told me to change from pants to skirt put the heels on and tie my white button up shirt just above my belly button . While I was changing she returned and told don I stepped outside to take a call and she was going to go help me find my way back. No more than 20 min later she lead me back downstairs in full girl mode wearing light makeup , bright pink lipstick and her perfume . The look on his face was priceless. She said " you said I couldn't distract you but you said nothing about him " she laughed handed me a cue and told me to do whatever I needed to do to win.
After my first shot it was clear I could not play wearing heels and girl cloths and that I was not going to win this way . I pulled up my skirt a bit and leaned over the table . He made a few more in and I grabbed his ass n showed him my panties . He must really want to go to daytona cause he made 2 more and was now on the 8 ball . She realizing I was going to lose grabbed the 8 ball off the table and said " if you make this shot we go to the race but if you miss you can do whatever you want to both of us tonight " . You could see him thinking about what to do she put the ball back on the table and he lined up his shot . He sunk it in the corner pocket with enough spin to bring the cue ball back down the table . The little white ball rolled right at the bottom corner pocket and stopped right on the edge . His wife looked disappointed and turned her head real quick he i guess had a change of heart because he tapped the ball just enough for it to drop in the pocket scratching and losing the game . Her face lit up like a little kid on Christmas she jumped up and wrapped her arms and legs around him as he set her back on her feet he said " time for you two to pay up for losing the bet now " remembering last time i was nervous and exited to see what was going to happen next.
She wasted no time at all grabbing my hand and his leading us both to the bedroom where my pants lay on the floor . Don pulled out 2 blindfolds and tied them tightly over both our eyes . He forced me onto the bed where I now lay listening to kissing n soft moaning . A few min later I felt her land next to me as he tossed her on the bed and he followed right behind . Almost emediately I felt her small soft hand stroking my cock . Hearing her soft moan getting louder my cock was rock hard when she stopped and asked if i wanted to taste her pussy? That was a no brainer of course I did it was a quick yes from me . Don made me beg for it , please let me taste her pussy . I repeated that 3 or 4 times he grabbed my head and stretched my lips around his cock in a deep stern voice he said " lick her pussy of my cock sissy" I swallowed it like it was my last meal . Her wetness mixed with his salty sweet pre cum was perfect . Some time went by and he moved back to her fucking her pussy while she stroked and sucked my cock . Relying only on touch and hearing as I was still blindfolded I could hear her pussy being fucked nice and hard with every thrust I could feel the force through the mattress and feel her muffled moans while her mouth was wrapped around the base of my throbbing cock . The noise slowed down and there was some movement around and I heard her say " baby I think its his turn " you think he deserves it? don asked . As she was saying yes I felt my hands being tied together with zip ties . Next thing I felt was my legs being pushed back with some force and I felt really cold lube being applied to prepare me for my turn .
I suddenly had a moment of anxiety and got super nervous as I just remembered how thick don was and how bad it hurt when he entered me last time but a deal is a deal and she said he could do anything he wanted as part of the bet . I tried not to tense up when I felt the head of it press against my ass but I couldn't help it but before I knew it I was penatrated and it was slowly going deeper with every stroke . Being told to just enjoy it and relax by don I layed there on my back legs pushed back being used like a sex doll . Skirt slid up to my waist panties pulled to the side I was in for whatever was going to happen. I remember thinking a few minutes in that something felt a bit different . I was getting worked over pretty good , fast mediocre thrusts but last time his manhood felt much thicker and he fucked me much harder . I thought owell maybe I don't remember everything correctly as last time i had much more to drink . I relaxed and started moving my hips really getting into it for a few minutes then I felt someone get off the bed and heard them walk away . I was still getting fucked so I figured she had gone to the rest room or something . There was no sound in the room except my pathetic little squeals and little girly moans . Two minutes tops went by and the other person returned climbing back onto the bed . I heard her ask if they should remove my blindfold don replied " why not but she said " wait a minute he needs more lipstick" . I could feel a very thick coat of lipstick being applied to my lips like it was being scribbled on with a crayon. Ok now remove the blindfold she said . When the blindfold come off I didn't know what to say. There she was on her knees wearing nothing but a strapon dildo pushing my legs back fucking my willing ass like she had something to prove . For a moment I lost track of my thoughts as the sight of her soft mature body was incredibly stunning. Her nice wide hips looked great with straps wrapped around them . Her nice round titts still sat up pretty high for being in her 50's her body had aged very well .
She then leaned forward grabbing my hip with her left hand , my throat with her right hand she whispered in my ear " I heard you fucking my husband from the other room last time , next time you ask my permission first you got that you little bitch? I tried to say yes but I could barely breath she was choking me pretty hard and she had buried that dildo to the buckle . She asked again " do you understand " letting off the grip a bit I gasped yes ma'am she replied "good girl" she then went back to her knees , slowly pulled out of me and removed her harness. She walked over to a dresser on the other side of the room and as she grabbed some lipstick from the top drawer she said to Don "I think we should play a game I know I can win" . She continued " this is how it works you have pink lipstick i have red we will each get 2 tries to take as much of his cock as we can the closest color to his balls wins and the loser gets fucked as hard as he wants " . I was up first and got half way down then gag reflex got me so I pulled out . Her turn she took probably an inch more than I did. My next turn i did great probably half an inch from his balls i figured I was safe . She smiled at me grabbed his balls and took it all leaving a nice red ring all the way around the base . Knowing I lost I knew what I had coming . His full erection was about as thick as my wrist .
Right away he stood me up , spun me around , slapped my ass and pushed me forward onto to bed . Remembering last time i got on all fours and waited . He straightened my skirt out and said " scoolgirl outfit is my favorite " then he reached underneath pulling my panties down and under my legs tossing them on the bed saying " your not going to need these anymore ". He spit on my ass slid 2 fingers in then 3 spreading the spit and remaing lube around good . With no time to prepare or brace for impact he slid in slowly . I could feel my ass stretching over his huge cock . He was balls deep within a few thrusts and steadily picking up speed. He was really having a go at it now .my eyes watering with eyeliner she applied earlier running down my face and steady sissy moans every time he slammed his hips off my ass .
It didn't take long for his wife to join back in laying in front of me legs spread apart rubbing her clit in fast circular motion. she was close to another orgasm when she slid down Missionary underneath me . She commanded me " rub your cock against my clit , don't even think of putting your cock in me and you cum after I cum . I shook my head yes and started grinding on her pussy . I now looked like a real girl enjoying getting fucked. Her hips rocking in circles my body now moving in rhythm with hers and him pounding away from behind . I was ready to cum but trying hard to hold back finally her body started shaking hips thrusting harder then she just let out a few loud screams and stopped moving . Not 30 seconds later I exploded hot cum right down the middle of her titts and across her face it didn't faze her at all . She then wrapped her legs around the back of mine and her arms around my waist pulling me in tight . Don cum in this little sissys ass she said . Realizing that I didn't actually know he was wearing a condom I tried to pull away but no way I could get free . Don was taking full advantage pounding my ass so hard it sounded like clapping, a few more hard pumps and he moved around face level he pulled the condom off he was wearing and filled her mouth with cum . I was so relieved that he was wearing a rubber and didn't fill me like a twinkie I didn't even notice that I was making out with his wife and she was tongue feeding me some of the cum she didn't swallow . It was my first taste of thick milky white cum and I surprisingly didn't mind it . We all showered together and I headed home. A week later I went to put my golf clubs in my car trunk and I found a big gift bag and inside was 2 pair of pantyhose knee high and thigh high stockings 2 sexy pieces of lingerie and the complete schoolgirl outfit panties and heels included along with a pair of season opener celtics tickets and a note that said I will see you at noon on October 17th my buddies are going to like you.
