The Office Sissy

i just returned home from dropping Jake off at the airport today.  He closed his firm at noon today, giving everyone the rest of the week off and had asked me if i could drive him to the airport.  i agreed and he told me to come on up to his office around 11:30 this morning. 

"Wear something pretty under you clothing.  It's time we play out that fantasy I told you about" he said. 

The fantasy?  my sucking his cock while he sat at his desk.

i was nervous all morning.  He not only insisted on something pretty, but i had to be wearing a bra.  i arrived at his office in stockings, garter, panties and a bra.  The bra was easily concealed under my shirt and jacket. 

His administrative assistant let me in to see him and it was evident she was getting ready to leave soon.  He told me to have a seat and take my jacked off.  "i prefer to keep it on i said" in a joking manner, a little concerned that Jackie, the administrative assistant would walk in and possibly see my bra or bra straps through my shirt.  "I said take it off" he said  in a stern manner.  i laid it over one of the chairs in front of his desk as sat in the other.

Jake made a couple of calls, both of them on speaker phone.  During the first call he walked over behind me and ran his hands over my chest.  It was more to feel if i was wearing the bra than any affectionate touching.  When he felt it i could tell he was pleased that i had obeyed, the groping turned into a softer touching with his fingers running along the outline of the straps as he continued to talk on the phone. 

As expected, Jackie did come in to announce that she was leaving for the day and wished Jake a Happy Thanksgiving.  Jackie, a very efficient looking 50-something year old woman, looked very nice in a greyish pinstripe business suit, white blouse and heels.  Jake saw me looking her over.  When she was gone, he said "I bet you'd like to be my secretary wouldn't you?"  We both laughed.

He then went over and locked the door.  "Show me what you're wearing" he said.  "Don't be nervous.  There's nobody left here.  Trust me."  With the door locked, i felt somewhat safe and began to strip. 
"All the boy clothes off" he ordered.  "Model for me" he said.  i slowly turned around to show him my lingerie.  My cock strained in the chastity belt.  It would strain for long time.

Jake dialed the phone and began to talk to a client in Wilmington Delaware, almost ignoring me while motioning that i stand next to him.  He sat there, rubbing my ass through the panties as he talked on the speaker phone.  He stood up and motioned to his crotch, indicating that he wanted me to loosen his trousers and start with his cock.  i did.

Soon, i was kneeling in front of him and kissing his crotch, balls, and cock.  He was put on hold briefly by the client during which time he had ma take his shoes and slacks off.  He stood before me and told me to start sucking him.  He finished the conversation in that position, wishing his client a Happy Thanksgiving and promising to touch base with him next week. 

There was one more call that lasted only 5 minutes or so.  I had his cock in my mouth the entire time, sucking but also trying to be quite with my slurps, kisses and licks.  By the time he hung up, he was rock hard. 

"Ready for a big load?" he asked.  i sucked and nodded at the same time.  "Beg for it."

"Please Daddy" i said in my softest and sexiest voice, looking up into his eyes. 

"No mess on the floor.  Promise?" he asked. 

"Yes Daddy, i promise." i said.

He grabbed the sides of my head and thrusted back and forth.  He went deep into my throat and i gagged several times, and i was careful that i caught the saliva mixed with precum that was dripping down my chin with my hands. 

Jake was farm more aggressive than usual - "I love it when you gag on my cock" he said passionately and immediately shoving it in deeper, causing another gagging reaction. 

"Ready?" he asked and without waiting for an answer shouted out "Here you go sissy!" 

Typically he enjoys cumming all over my face but not this time.  He did his best to stay in my mouth and i did mine to keep him there.  It was a totally different sensation, large spurts of his semen hitting the back of my throat and filling my mouth, only a small portion finding its way to my lips. 

i was proud, i don't think i spilled a drop.

We came down from our high, got dressed and made our way to the airport.  Naturally, there was no good bye kiss.  Instead, there was a slight caress of my thigh, with a "love tap" on my CB-3000.

"Be a good girl while I'm gone" he said as we pulled up to the curb.  "Some day, I'd like to have you bent over my desk.  Would you enjoy that?"

"Yes Daddy, i would" i said with a very content smile on my face.

It was a very, very, very sexy and gurly afternoon!


sissy terri