Well this all happened two weekends ago. My boyfriend Jake's father was turning 45. Seeing his wife left him a couple of years back and not dating at the moment. We decided to take him out for dinner and maybe some drinks.
Jake still lives with his father even though he's 23. Seeing its a huge house and they both run a landscaping business together it works for both of them. So there they were about 5:30 pulling into my driveway with Jake's truck. Not the work truck but his new Dodge. Even though it was winter in the North-east and fairly cold I decided to wear my black skirt with a light white top.
Throwing on my long coat I went outside where William was waiting with the door open so he could help me get in between them. Sliding over to Jake I gave him a hello kiss to which he said "Don't forget the birthday dad," he said smiling. I turned to his dad grabbed his head and planted a big kiss on his lips.
"Happy Birthday!" I said smiling.
Off we drove off. There I was sitting beside 2 big men. Jake looked like a younger version of his father. Bill had his arm hanging on the seat behind my head. His arm kept slipping down and landing on the back of my neck. After saying sorry for the third time.
"If your gonna keep doing that you might as well leave it there and give me a massage," I said laughing. "I would give you a good one but your coat is in the way," replied Bill with a sly grin.
"No problem," I said unzipping my coat an pulling it off my shoulders.
"There," I said, " Work your magic!"
It felt a little strange at first have his father massaging my neck but after a few minutes of his strong hands working my muscles it started to feel good. Way to good. I closed my eyes lowered my chin to my chest and let my body go limp. I have to admit it my body started to react to his attention. I could feel my nipples hardening under my blouse and a little moisture between my thighs. I'm sure they both heard a couple of unintentional moans. Even though it was a 40 minute ride I, opened my eyes and realized we arrived. Entering the restaurant Bill excused himself to the rest-room.
"I see you really liked my fathers massage, your nipples are still hard," said Jake leaning in to me.
"He has very strong hands," I replied trying really hard to hide the fact that I was blushing.
"Maybe you should return the favour on the way home," added Jake cheekily.
"Can't really reach back there he's to tall," I shot back nervously.
"That's not the area that I think he would like massaged" he said smiling and leaving me completely speechless.
"THAT'S YOUR FATHER your asking me to jerk off!" I said finally getting over the shock.
"But its his birthday and it's OK with me," Jake said.
With that I said "we'll see but you better get me some drinks," Bill returned and we went to the bar before are table was ready.
Our table was ready in about 20 minutes and with my second margarita in hand we sat down. Now it was my turn to excuse myself to the powder room. Once in there I looked at myself in the mirror to try to figure out my next move. Never have I ever thought of doing something like that with an older man never mind my BF father with him next to me. His massage was great and I started wondering if the son got his cock from his father. I thought if I tried something he would probably stop me. With that in mind I headed back to the table but not before releasing one more button on my blouse.
Both men were gentlemen and stood on my return and Jake gave me an little wink noticing my opened blouse. He also said he ordered me and his father another drink. So we got down to the business of ordering our meals. Everything sounded so good that none of us could really decide. So we all chose a dish that we liked and we were all gonna share. Couldn't help catch Bill glancing down my blouse a few times. While waiting for our food to arrive we just made small talk about life, weather and my school. Telling them I'm almost done getting my business degree.
"Ya know Jake," Bill said "business is good and we were planning on hiring someone to work the office and do the scheduling and the books. Maybe Hannah could come work for us. She would sure pretty up the office,"
The drinks had clearly had an effect on me when I said "Sure that would be great and I'm sure I would have to take care of my bosses,"
"No but that would be a big perk for you," Bill said laughing.
Thank god the food arrived and it all looked? fantastic. We all dug in and shared each others meals. Picking off others plates an being fed by two handsome men was very arousing. Between the drinks and all the flirting got me thinking about Jake's request, I thought to my self that I might as well give it a shot. Finishing our meal Jake paid up while Bill went to get our coats. This time I didn't zip it up.
Stepping outside we were all surprised to see it was snowing heavily and there was a inch or more on the ground. Jake went to get the truck while we waited at the doorway. Feeling a little buzzed I held onto Bill's arm to steady myself. When Jake pulled up " Damn now my feet are gonna get all wet and cold," I said shivering to emphasize my point. With that Bill swooped me up in his arms and carried me to the truck. He opened the door with one hand while still holding me sliding me onto the seat. Doing this made my skirt rode 3/4 up my thighs. I didn't try to straighten out I just closed my coat. Bill got in an off we went.
Little ways down the road I let my hand drop on Bills thigh. Patting it I turn to Jake and said what a sweet man his father was for carrying me to the truck. He and Bill just laughed a little. I left my hand on his leg and soon my fingers were starting to massage him. That's when I thought the fun was over because he placed his hand on mine and stopped me. But to my surprise he just did that so he could unzip his jacket. He then took my hand and placed it a little higher on his leg and used his hand on mine to start massaging him. He stopped but my fingers kept on going moving up ever so slowly up his body. Reaching the front of his pants I could feel that I was doing a good job. I could feel his hand slowly undo his belt and unzip his pants. That made it easy to slip my hand into his briefs to find I wasn't going be disappointed by the big package inside.
Just then I felt Jake's hand on my bare leg "told you Dad, my Hannah is one hot woman," said Jake proudly.
"DAMN right she is didn't think she would do it!" He laughed back.
"Now keep your eyes on the road don't want to land in a ditch," He commanded Jake.
I should of been mad for being set-up like but now I was horny as hell so I didn't give a flying fuck. I turned my body to him so I could get both hands around his hard cock. As I stroked him he lowered the back of his seat and pulled me closer too him grabbing my head so we could kiss. Our lips connected and out came our tongues to explore each others mouth. His hand then slipped into my blouse to play with my hard nipples. His cock was so hard I thought he was gonna explode right there. I started to slow down but he told me to keep going. When he lowered his mouth to my breast I couldn't help but let out a loud moan.
"Suck my cock Hannah!" he whispered in my ear seductively " I want to feel your mouth around my cock" he ordered me and I wanted to obey is orders so badly.
Lowering my mouth I slowly stuck out my tongue to lick his swollen head. His cock was just as long as his son but a little thicker. Cupping his balls with my hands I opened my mouth and started sucking. That got an instant moan of pleasure. I could feel his hand working its way up my thighs so I spread them open so he could get to my pussy. His eyes opened wide when he got there to find it bare and bald. Running his finger over my clit made me quiver and go deeper down on his cock. Spreading my lips he inserted his finger deep inside.
