Second Date
- 3 years ago
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Shelli's Second Date free porn video
Shelli's Second Date
As I closed the door, I felt slightly lightheaded and needed to sit down.
This was not at all what I had expected. I had agreed to my first date
with Tom at the urging of my boss, Gwen Taylor. Since I was several
months into my transition, Gwen felt I needed to get out and begin living
my life as a young woman outside of my time at work. This included
starting to date guys. Gwen made this sound so easy and innocent that I
couldn't help but agree to it. I will admit that I enjoyed everything
leading up to it - the flirting, making sure I looked my cutest when Tom
was around, shopping, getting a makeover at the salon and the nervous
anticipation. What I hadn't expected is how wonderful the date itself
was! Tom was a perfect gentleman. All the little things he did (opening
the car door, holding my chair at dinner, helping me on with my cover)
made me feel even more feminine. Sitting together at dinner, we were
close enough to touch and gaze into each other's eyes. I think my outfit
and makeup were perfect - he couldn't seem to take his eyes off of me.
The kiss? I certainly hadn't expected it to feel like THAT! I didn't
really know what to expect, but OMG! Whether it lasted 5 minutes or 5
hours, it still would not have been long enough!! While the kissing
started out as sweet and tender, it grew into a long, slow, passionate
make out that made me wonder about asking him in. I broke it off because
I wasn't sure I could control myself and was confused about these new
found urges. The kissing made me tingle from head to toe and the more
our bodies came together in a warm embrace, the more I wanted. Was it
the hormones? Was it the real me? Where would this lead? This was all
more than I could contemplate as I slipped into a satiny baby doll and
crawled into bed.
At work Monday, I found a single pink rose on my desk with a note from
Tom "I had a great time with you this weekend, Tom"
As I was reading the note, Gwen walked over with a smug smile on her face
Gwen: "How did the big date go?"
Shelli: "Great, we really had a good time"
Gwen: "Since you are kind of new to these things, it looks like you
officially have a new boyfriend"
Shelli: "Oh please, we just had one date"
Gwen: "Did you kiss him goodnight?"
Shelli: "Yessss" I blushed slightly.
Gwen: "And it was....?"
Shelli: "Fantastic!" I blurted out before I could get it back.
Gwen: "I hope you invited him in for a "nightcap"
Shelli: "I didn't want to rush things for a first date." I stammered,
blushing a bright crimson.
Gwen: "That's okay. But it's also okay to have new urges and desires -
it goes with the territory. You obviously enjoyed the goodnight kiss,
it's only natural to wonder about the next step"
Shelli: "What is the next step?"
Gwen: laughing I am sure that will come soon enough"
Over the next few days, Tom stopped by at my desk for visits. We flirted
shamelessly and with each visit I found myself wanting to present a more
alluring Shelli. I unconsciously chose tops with a lower cut and bras
that would enhance my bust. I also chose lacier, satin bikini panties to
match the bra. While Tom couldn't see the panties, it made me feel
sexier and more feminine. I found myself wearing only 3 ? to 4 inch high
heels because of the way they made me look and feel. It seemed just
being near him gave me the overall tingling feeling I had had with the
first kiss. I wanted to touch him and feel his lips on mine so badly it
made me crazy. After a few days of this, I agreed to meet him out for
drinks on Saturday night. I had to tell Gwen.
Shelli: "Big news. Tom asked me out on a second date"
Gwen squealed with delight. "I guess we will need to go shopping for a
new outfit."
Shelli: 'I am sure I have something that might work, but if you insist on
a new outfit, you are the boss."
Gwen: "What sort of look are you wanting?"
Shelli: "I am not sure what you mean."
Gwen: "It's a second date and I can tell how much you like him by the way
you look at him. What do you want your outfit to say to him?"
Shelli: "Cute, understated, but sexy"
Gwen; "It sounds like you are trying to seduce him."
Shelli: "Yes, that sounds like a good way of putting it."
Gwen and I went shopping later that week. As always, I enjoyed the time
to be totally girly and also enjoyed immensely Gwen shaping me into a
mature, confident woman. "There is nothing sexier than confidence" Gwen
always used to say.
Gwen felt I needed an outfit that would show Tom a confident, sexy woman
without being too slutty. We decided on a snug fitting charcoal colored
sweater dress to show off my developing curves. To accentuate my hips
and bust, we added a wide black leather belt. To make sure the curves
were perfect and no unsightly bulges peeking thru, Gwen also fitted me
with the appropriate shapewear. We topped it off with black, ultra sheer
hose.
We debated about the appropriate footwear, but Gwen ultimately convinced
me to go with knee length, black boots with a 4 inch heel. They were made
of the softest black calfskin and had a gold buckle on the side. I felt
so incredibly sexy just trying them on, I couldn't imagine how I would
feel with the whole outfit together. "You are certainly going to stun
him with this outfit. He is going to take one look at you and his jaw is
going to hit the floor." I giggled as this was exactly what I was hoping
would happen.
On Saturday, Gwen accompanied me to her spa, where we both had facials
along with a manicure and pedicure. She helped me pick out a nail and
lip color that would go with the outfit. We spent some time with the spa
cosmetologist (Brittany) selecting the makeup look for the evening.
"What look are you hoping to achieve?" Brittany asked. Before I could
answer, Gwen answered for me "Evening look, seductive, second date,
hoping to get in his pants." "Gwen!!" I shouted with shock and a little
embarrassment. "I am just telling her what you want to say but won't"
Gwen responded with a devious grin on her face. "Oooh! Sounds like you
are going to have a romantic evening with a special guy. Don't worry, we
are going to make you look fantastic. Long feathery lashes, a smoky eye
shadow, full pouty lips - it will make him absolutely melt." Brittany
responded.
Brittany did a phenomenal job with the makeup and hair. The lipstick was
a medium red and perfectly matched my nails. I got home in just enough
time to change into my new outfit. It did look sensational! I had
achieved just the look I wanted and hopefully Tom would approve. I got
my answer an hour later when Tom arrived to pick me up. "You look
incredible tonight!" he exclaimed. I answered him with by whispering "I
am glad you like it, dear" before planting a soft but full kiss on his
lips.
Tom took me to a new club where we chatted and laughed while gazing into
each others eyes. While sitting, he gently carressed by stockinged legs,
allowing his hand to inch up my thigh. The boots must have worked since
he couldn't take his eyes off my legs. After a few drinks, we decided to
make it an early night out. I had enjoyed his attention and touch so
much that I didn't want the night to end. Once we got back to my place,
I asked him if he would like to come in for a drink.
I poured us each a glass of wine as I sat down on the couch close to Tom.
The heat of his body and his touch were driving me crazy. He leaned in
closer as I guided my lips to his. Like the first kiss, I felt a jolt of
lightening go through me followed by a warm tingling sensation. Also like
the first time, the kissing became more passionate as I put my hands
behind his head and tousled his hair as I pulled his mouth more tightly
to mine. I was becoming more aroused as I closed my thighs together,
preventing my member from spoiling my appearance. As I was reaching my
hand into his shirt, my elbow rubbed against a growing bulge in his lap.
After several minutes of stimulating him "accidentally" with my elbow, I
slowly reached down with my hand to caress his erection. It was almost
like an out of body experience - I was watching my hand do something I
couldn't believe but had no control to stop. I caressed the shaft with
the butt of my hand but concentrated on the head. This seemed to excite
Tom as he began to squirm and kiss me more deeply. It certainly aroused
me! Without thinking about what might come next, I slowing unbuckled his
belt, undid the button and unzipped his fly. His penis was rock hard and
the head was sticking out of the waistband of his briefs.
Almost unconsciously, I lowered myself to my knees between his legs. I
gently pulled down his pants and briefs as I settled comfortably into a
kneeling position, comfortably resting my butt on the backs of the heels
of my boots. His erection was beautiful - long, pink and hard. I slowly
began to kiss along the length of the shaft, using my tongue to lick each
of his balls. I left tiny lipstick kisses along its length as I kissed
slowly toward the head. When close, I grasped his member and imagined
the head were an ice cream cone as I wrapped my lips around it and
sucked. Slowly, I repeated this maneuver, taking more in my mouth with
each repetition. After a few minutes, I grasped the base of his penis
with my right hand and increased the lip pressure along the length of his
cock. I could taste my lipstick as my glossy, plump lips enveloped him.
I maintained eye contact as my head began to bob up and down. I had
fantasized for so long about giving Tom the best head ever and now it was
coming true!! Just as my saliva was starting to give out, I tasted the
thin, salty pre-cum in my mouth. This provided just the right amount of
lubricant to make his cock slick and make my sucking more enjoyable. I
felt his hips begin to thrust and he forced himself in and out of my
mouth. Sensing a climax approaching, I gently squeezed his balls with my
left hand. I was so turned on, I came. Since my member was tucked
between my legs toward my ass, the warm semen began to seep around and
into my anus as I moved back and forth. As I enjoyed the warmth I felt
his cock convulse as my mouth filled with a slippery, salty reward. I
was unsure how this would be, but I relished the taste of his cum as I
swallowed. His cum provided additional lubrication as I sucked and
bobbed with greater speed and vigor. After swallowing his entire,
delightful offering, I cleaned up by licking an excess that had dribbled
onto his groin. With his cum still on my lips and breath, I gave him a
deep probing kiss. He kissed me back without the slightest hesitation.
He didn't seem to mind the taste of semen in the least. Perhaps he would
reciprocate one day?
To be continued...
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