Mr. and Mrs. Flannegan Part: 2
I awoke the next morning still in a haze, questioning if the previous night's events had really taken place. Looking over at the night stand I picked up my phone and went to my messages. Looking through them I confirmed this did in fact happen.
The next couple of days were uneventful. I did not see any sign of Mrs. Flannegan, and was too nervous to go to their house to use Ted's equipment. Mr. Flannegan returned from his business trip and life continued as usual. With Mr. Flannegan home I returned to using Ted's pc.
One night while I was in Ted's room gaming on his computer his mother came in and sat on the bed behind me, quietly waiting for me to finish. I turned around shortly after and as I start to speak she interrupts me and says "Hello Josh, As you may or may not have noticed, Mr. Flannegan is out on business and will not be back till tomorrow morning." As she speaks she fiddles with a piece of paper in her hands. "Now being a woman of opportunity I figured what better time to come check on my son's good friend Josh" she giggled. Turning the paper over in her hands I was stunned in fear realizing the contents that lie upon them. To my horror on the paper was photos, taken from the day Mrs. Flannegan came to my apartment.
The pictures showed crystal clear images of me, standing in front of the couch in a woman's thong, My penis fully erect as I had just finished in Mrs. Flannegans mouth. The pictures were damning as she was nowhere to be found in them. Confused as I saw her put her laptop away, I looked up from the pictures in front of me to speak. A wide grin was apparent on her face as she watched me squirm and blush looking for the words to speak. Before I could find them she asked "My dear Josh you must be wondering how I acquired these photos." As she spoke she lifted her bag up off the table, flipping it upside down. As she did this it became obvious that a camera was sewn into the fabric of the bag, Recording our every move.
"Now Josh, I wonder what Ted would think knowing his friend Josh was a panty wearing sissy.. Do you think he would continue to be your friend knowing you not only wore a woman's thong, but you had a cute little boner to go with it? What would that girl at the movie store you always talk to think? What was her name Jessica? I see you eyeing her up from the aisles, too afraid to approach her."
Scared out of my mind I looked at Mrs. Flannegan with pleading eyes. "Please Mrs. Flannegan, please dont' show anyone. What can I do to make you delete these pictures and the video?" I asked frantically. Giggling at me she looked me back in the eyes, knowing she had me defeated. She said, "Well my pretty young lady, I'm glad you asked! You see I have been pondering upon the same exact question and I do believe I have come across a good solution."
"I have come up with a list of things that I will require before I let you go and delete these photos. All of which will be completed here, and now." she said as she flipped to the second page in her hand. "First you will come with me, I will run you a bath and we will shave off that icky boy hair plaguing your legs and chest, not that there is much to begin with. Second, when I have finished shaving you, I will dry you off and lead you to the second spare bedroom."
"We have always kept this room locked, The reason being that the stuff inside belongs to Ted's cousin. I'm sure you have heard plenty about her, as it just so happens you both wear roughly the same size. It is simple, I will present you another pair of her panties. You will put them on and model them for me. After which you will start your third and final task. You will pleasure me properly. When all of this is completed I will reward you IF, you are good."
As she spoke I knew I didn't have a choice. My cheeks burned red with embarrassment as she commanded me to follow her to the bath. Inside the room I was told to take off all my clothing. Setting them aside as the bath finished running I looked at her waiting for her to leave the room. Looking back at me with amusement she grinned, "Well, what are you waiting for my dear? I'm not going anywhere, remember? I said that I was going to shave you. I said nothing about you doing it yourself. How am I to know if you are doing it properly? I would hate for you to hurt yourself." she giggled.
For the hundredth time my cheeks burned with embarrassment as I stepped into the bath. For the next half hour she ran the razor all over my body from the neck down. Then she had me step out of the bath. "Can you pass me the towel?" I ask. "No my dear, you are not finished yet. Come here and bend over the sink." she said. Hesitant I moved forward to the sink, as I arrived in front of it she placed a hand on my hip and one on my back bending me over the sink. "Grab onto the sink for balance" she said.
Grabbing onto the sink she stepped back grabbing the razor, running it up my butt cheeks. I let out a yelp as I felt her fingers spread my butt cheeks apart. She giggled and ran the razor up and down my crack, shaving me to completion. "A woman always shaves her pussy." she giggled as she handed me the towel. Amused at how easily she could make me blush.
"Now come with me Josh it is time for stage two of our evening of fun together." She led me through the house to the guest bedroom unlocking it, pulling me inside by my hand. Sitting me down at the chair in front of the desk I quickly realized it was a vanity. "I know I said you would only be wearing the panties again but seeing you all smooth I can't help myself but go all out." As she spoke she applied make-up to my face.
Fifteen minutes later and she had finished. "You look amazing Josh. Come and sit on the bed" she said as she moved me to the bed. Turning to the closet and dresser she started to pull out clothing one by one. First she took out a set of hot pink lingerie with black lace trim and laid them on the bed. She continued her search as she pulled out a pink sundress and laid it on the bed by the lingerie.
"Alright Josh. You are going to put these clothes on. If you do everything that I say, I will reward you as well as delete those photos. Here is some lingerie you are to put on under this sundress. Put them on slowly now while I watch." Nervous, I watched as she grabbed the stockings moving in front of me. She said "I want you to notice how they feel going up your silky smooth legs my dear." handing them to me. Blushing, I Took the scrunched up stocking and began rolling it up my legs.
The sensation was astounding. The connection between the fabric and my skin was unlike anything I had felt. As I got to the top pulling it as far as it would go she handed me the other one. I grabbed it from her and put that one on slow like she told me to, feeling the fabric slide against my smooth leg once again. As I got to the top I looked down. To my shame all these new sensations mixed with this beautiful woman standing here watching me had caused the blood to rush to my small cock.
"Oh my Josh, what is happening down there?" she giggled as she pointed to my penis. Blushing, I turned away as she giggled. Picking up the garter belt she handed it to me. I slid it up to my hips and connected the straps to my stockings. Next she handed me the panties. Frilly as can be I slid them up my stockings until they sat in place. My penis strained against the fabric, trying to break free.
Giggling at me she says "Poor thing, your tiny little penis is trying with all its might to fight against the girly feminine panties but it can't even muster to lift them off your skin." walking up as she spoke, she put her hand on my crotch rubbing me through the panties and giggling. "Now for the dress!" She said as she removed her hand, picking it up and helping me into the dress. Zipping it up in the back she sat me down at the vanity again. Facing away from the mirror. Returning to the closet she pulled out a wig of blonde hair. Walking back to me she fastened it onto my head, adjusting it so it was just right.
