Heather s Special Weekend
- 3 years ago
- 50
- 0
The Weekend Trip free porn video
Where to start? My girlfriend, Patti, knew and tolerated my
crossdressing. She did not do anything to encourage me, until now. We had
planned a long weekend to an old mountain mining town, now a tourist
haven. Her suggestion caught me by surprise.
She mentioned that this would be an opportunity for me to spend the
weekend enfemme! I was shocked by her suggestion, but elated. Now, I had
to get all the details worked out.
First, I made an appointment at a local salon for the morning of our
departure, two weeks from now. Next, I shopped online like crazy for some
appropriate outfits. Don't want to look too out of place, but still want
to look feminine. I found a couple of dresses that looked comfortable for
travel - we would be driving 5 hours each way. Then I found 3 nicer
dresses for evenings and dinner. I also found 4 outfits that would be
good for daytime excursions. I already had shoes, wigs, lingerie, etc.
On the evening before our departure, I spent several hours shaving and
using lotion on my entire body. The next morning, I got up early,
attached my C-cup breast forms with latex glue, put on lingerie, wig,
shoes and a travel dress. Wearing my sunshades, I looked passable and
headed out to the salon for my appointment.
When I arrived, a little early, there were no other customers in the
shop. I had scheduled a mani-pedi and full make-up. The nail tech didn't
even blink when I sat down, she asked what color polish. I picked out a
pastel pink for toes and fingers which matched accent colors in my dress.
She promptly began shaping my nails and applying polish. When completely
dry, she had me move over to the make-up station.
The make-up lady smiled and made small talk, asking how long I had been
crossdressing - guess she wasn't fooled. We chatted as she applied beard
cover and foundation. Coordinating with my nails, she used light pink eye
shadow and then applied mascara and eye-liner. She suggested a lip gloss
that matched the eye shadow. After she was done, she spun the chair
around so I could see myself in the mirror - I didn't even recognize
myself!
When we were done, I asked if I could also purchase the nail polish, eye
shadow and lip gloss they had used on me. I checked out and went to my
SUV and drove to pick up Patti at her house. Patti answered the door bell
and was shocked at my appearance - she almost didn't recognize me as
well. She was thrilled that I looked so good - much better than she had
anticipated.
As we had plenty of time for our drive, I suggested to Patti that I might
pleasure her orally before we left. She didn't even blink, dragging me
over to the couch where she lay back and pulled her panties off. I knelt
and began tittilating her with my tongue, until she was totally exhausted
and pushed me away. I went into the bathroom to repair my make-up, that I
knew had been wrecked! Finishing, I also refreshed my lip gloss and went
back to see if Patti had recovered. She was still reclining on the couch
and said this could be the start of a very enjoyable weekend!
We loaded her luggage into my SUV and started out. About 2 hours into the
trip, we both needed a potty break. I pulled into a convenience store and
filled with gas while Patti went to the restroom. She came back out and
told me it was my turn. I went inside and had to consiously remember to
go to the women's room! No issues, and I came back out and we continued
our trip.
When we arrived at the condo complex check-in office, Patti stayed in the
SUV while I went to check us in. I was nervous, the reservation was in my
name, and my credit card asked that you check my ID. There were 2 women
in the office. One had a name tag: Tiffany and she was from Florida; the
other was Tanja from Colorado. Tiffany commented that she really liked my
dress - she said it was very cute. I thanked her and gave my name for the
reservation. She looked up at me with a big smile, and said I don't look
anything like my name. I blushed, and responded that I had lost a bet
with my girlfriend. She instantly asked where is this girl - and I
pointed out to my vehicle. She told me to go get her, she wanted to talk
with her right now. I went out and told Patti that Tiffany in the office
wanted to talk to her. She reluctantly got out of the vehicle and walked
into the office. Both Tanja and Tiffany gushed that Patti had done a
fantastic job transforming me and that I looked wonderful. She didn't
tell them I had visited a salon earlier, just acknowledged their praise.
Tanja gave me our room keys and Patti asked Tiffany for dining and other
general places of interest. The 2 women were all gushy, giving Patti
several recommendations and suggestions. Tiffany leaned over to Patti,
and in a whisper, asked her a couple more questions, to which Patti
nodded and smiled. Then she wrote some information on a slip of paper and
gave this to Patti, who put it in her purse without comment. Both of the
women looked over at me with big smiles and asked that we come back
tomorrow with reports on our visit.
We drove over to the condo, which had an attached garage, pulled in, and
unloaded all our luggage. I took my dresses out and hung them to let some
of the wrinkles fall out. It was still too early for dinner, so I
suggested a celebratory martini. Patti thought that was a good idea and I
made a large shaker of cosmos. We sat down and clinked our glasses -
toasting to our trip.
Once again, I suggested to Patti that I might pleasure her orally before
we left for dinner. Again, she didn't even blink, dragging me over to the
couch where she lay back and pulled her panties off. I knelt and began
tittilating her with my tongue, until she was totally exhausted and
pushed me away. I went into the bathroom to repair my make-up, that I
knew had been wrecked! Finishing, I also refreshed my lip gloss and went
back to see if Patti had recovered. She said that this weekend was going
to be what happens when I am dressed, I would be dressed from now on!
We decided it was time for dinner and drove down to the small town. Patti
directed me to one of the establishments suggested by Tanja & Tiffany
from the condo office. I parked and we walked over and into an old
bar/restaurant. The hostess, Laurie, took us over to a table near the
back wall. Patti asked her what the bartender's name? She replied Ashley
and Patti turned and told me she would be right back, and walked over to
the bar. The bartender was a gorgeous red head with an award-winning
smile and full d-cup breasts! Patti leaned on the bar and asked Ashley
some questions, to which Ashley nodded, looked over at me, and smiled. I
had no idea what was going on, but figured to go with the flow and let
Patti lead the way. Patti returned to the table sporting a big smile, sat
down and said that the evening was going to be an adventure. We looked at
the menu, and our waitress, Leslie, came over to see what we wished to
order. We both opted for something light and therefore a glass of Pinot
Grigio to drink.
While we were waiting for our dinner to arrive, a stately woman
approached our table and said that Ashley had asked her to visit us. She
introduced herself as Kim,the owner of the restaurant / bar and wanted to
welcome us. She asked if we had plans for the weekend or would we like to
join her for an evening. Patti immediately said that we would love to
join her. Kim suggested that we meet at the real estate office around
noon tomorrow and left.
About the time we finished our meals, a young gentleman came over to our
table and introduced himself as Randy. Patti told him her name,
introduced me as Kathi Jo, and asked him to join us. He sat down and
smiled at me and said that Kim had suggested that he visit with us. I
just sat there and let Patti handle the conversation. Patti asked Randy
if he would be interested in entertaining two women for the evening, to
which he eagerly said Yes! Randy asked if we wanted to go dancing, or
just hang out and see the sights. Patti asked Randy if he would be
interested in going back to our condo for a martini. He said yes and
asked where we were staying. Patti told him the name of the condo complex
and the unit number - he said he would be there shortly.
We returned to where we parked and drove back to the condo. Patti didn't
offer any explaination or tell me what was going on, and I didn't ask.
When we got back to our condo, Patti asked me to make a shaker of
martini's.
Randy knocked on the door a few minutes later and Patti answered and
asked him to come in. I poured 3 martinis and offered one to Randy and
another to Patti. We clinked glasses and sipped our drinks.
Patti proceeded to explain to Randy that I was not what I appeared, that
I was really a guy in a dress. He simply smiled at me and nodded that he
understood. That I was embarassed would be an understatement! She then
explained that, as a woman, I had never given a blow-job, and asked Randy
if he would like to be my first. I was shocked at her nonchalance. Randy
stood up, un-buckled and pulled his jeans down to his knees, then pulled
his boxers down exposing his growing penis. Patti told me that I should
get on my knees and give Randy my very first blow-job. Not knowing what
else to do, I did as instructed. I began licking the tip and the shaft,
then took as much as I could into my mouth. Patti was watching intently,
giving encouragement and instructions on how to pleasure Randy. I felt
him growing harder and continued to suck back and forth on his shaft. He
then erupted into my throat and I did everything I could to swallow his
entire load. I got most of it, but some dribbled onto my chin. Patti
whooped joyously at my accomplishment, used her finger to wipe the excess
from my face, and then fed it to me to lick off her finger. I was still
trying to figure out what had just happened.
Patti jumped up and poured each of us another martini and toasted my
accomplishment. I drank some to clean out my throat.
Randy sat down, still with his jeans and boxers around his knees as if
waiting for something to happen. Patti then asked Randy if he wanted to
take me up the ass! I was again shocked at how simply she made the
request. Randy suggested I needed to suck him to get him hard again.
Patti told me to give Randy a partial blow-job, just to get him hard. It
took a little while for him to recover and then he pulled out of my mouth
and told me to bend over the back of the couch. Patti tore open a condom
and slid it onto Randy, stroking him as she did so. He came up behind me,
pulled my dress up and my panties down and pushed his penis against my
anus. I was nervous and tense. Patti came over and put some KY jelly on
her fingers and stuck them up my ass. That was a new experience! Randy
was then able to penetrate me and fuck me until he exploded again. He
pulled out and took some tissue to remove the condom and thru it in the
trash.
Randy pulled up his boxers and jeans, finished his martini, thanked us
for the evening, and left.
Patti was overjoyed that I had been deflowered and described the emotions
she had while watching. I was sore, and it was late, so I suggested we
call it a night. We both went and removed our dresses and lingerie, then
our make-up, and put on nighties. Once again, I suggested to Patti that I
might pleasure her orally before we went to sleep. Again, she didn't even
blink, laying back on the bed and pulled her panties off. I knelt and
began tittilating her with my tongue, until she was totally exhausted and
pushed me away. She again said that if this is the treatment she gets
when I am dressed, I will be dressed always!
We woke the next morning and showered, I had to shave, and do our make-up
and get dressed for the day. I put on another cute dress and Patti was
again excited at how totally feminine I looked. For breakfast, we went
back into town to one of the many restaurants. After eating, we wandered
around, window-shopping and checking out the sights. We found the real
estate office that Kim had described, and when she saw us, waved at us to
come in. We went into the office and Kim asked how we were enjoying our
time in her little town. Patti answered that we had met the wonderful
guy, Randy, whom Kim had sent to our table last night. Kim and Patti
chatted more about what we did. Patti offered that I had given Randy my
very first blow-job and that he had taken my cherrie! I was mortified
that Patti was volunteering this to someone we had just met! Kim smiled
broadly at me and asked if I had enjoyed the experience, and would I like
another episode. All I could do was smile and nod, yes. Patti & Kim then
proceeded to make plans for the evening. We were going to join her at the
same restaurant we were at last night for dinner, then back to her place
later.
Returning to the condo, Patti suggested that I put on my nicest dress, an
empire waist with a plunging neckline. I had no idea what was going to
happen for the evening, but just got changed and fixed my make-up. We
went back into town and met Kim at the restaurant. Kim was chatting with
the bartender, Ashley and introduced me to her. She smiled, knowingly,
and asked if I had enjoyed myself with Randy last night. I was moritified
that it seems everyone knew of my sex life! All I could do was smile and
nod.
The waitress, Leslie from last night, came over, gave us menus and
chatted with Kim. We all ordered drinks and dinner. After we finished
dinner, Kim suggested we go over to her house for more drinks. She gave
us the address and directions and we all left.
The trip to Kim's was quick, and I parked in the driveway. Kim opened the
front door and ushered us in to a beautiful ranch-style house with a
beautiful view of the nearby mountains. It was approaching sunset and the
colors over the mountains was spectacular. Patti & I opted for white
wine, and Kim poured 3 glasses and proposed a toast to my new life-style
as a woman! We sipped wine and then the doorbell rang. Kim went and
answered, and came back with Randy. Randy said hi to everyone, and gave
me a big smile. I had an idea what was going to happen next. Kim asked if
I was ready for a repeat performance, and I had no choice but to agree.
Patti was smiling in anticipation of upcoming events.
To turn the tables, I asked Kim if I might pleasure her orally before we
got started for the evening. Patti looked at me in amazement, but with a
big smile. Kim looked astonished, but stood up and came over to me, took
my hand and led me over to a couch. She then pulled off her shorts and
panties, lay down and invited me to begin. I knelt and began tittilating
her with my tongue, until she was totally exhausted and pushed me away. I
went into the bathroom to repair my make-up, that I knew had been
wrecked! Finishing, I also refreshed my lip gloss and went back to see if
Kim had recovered. She was still reclining on the couch and said this
could be the start of a very enjoyable friendship!
Meanwhile, Randy had taken the opportunity to satisfy Patti in the same
manner. When he finished, Patti went to the bathroom, and I went over to
Randy and asked if he was ready for me. He stood, unbuckled and dropped
his jeans and boxers, and I knelt and took him in my mouth as if I was an
old pro. While I was sucking on Randy, Patti returned and she and Kim
began to encourage me. It didn't take long and Randy gushed his load into
my mouth. I did better this time, swallowing the entire load without
spilling any! Patti and Kim were both congratulating me on my
performance. Randy stood up and embraced both women and began kissing
them, and they began disrobing completely. I decided I should join them,
and took off my shoes, dress and bra, leaving my panties on to contain
myself.
Kim looked at me and nudged Randy in my direction. He didn't need any
encouragement, but did stop to put on a condom before moving me to the
back of the couch. Randy entered me much easier than the night before,
and pumped several times before unloading.
While Randy was penetrating me, Kim & Patti had been exporing each other.
When he completed, he backed out and pulled his boxers and jeans back on.
He then went over where the girls were together on the sofa and kissed
Patti deeply and then Kim and left. What, I didn't even get a kiss?
Kim came over to me and began fondling me and asked if I needed relief?
When I nodded yes, she knelt down, pulled my panties aside and began
giving me a blow-job! Patti watched with a big smile and asked how I was
enjoying the weekend. Kim brought me to an explosive climax, and then
came up and gave me a deep kiss, feeding me a mouthful of my own cum. I
swallowed and then sipped some wine.
We sat on the sofa and Patti told me how thrilled she was that I had
taken to being fully feminized. Kim expressed her admiration of how
quickly I had adjusted to being fully feminine. We drank more wine, and I
scooted over and went down on Kim again, working my tounge in her until
she pushed me away. She lay back to recover and I moved over to Patti and
repeated the pleasure for her. When all done, we cuddled and kissed and
had some more wine.
I got up and went to the bathroom to repair my totally trashed makeup.
When I returned, I put on my panties, bra, dress and shoes. Patti had
already gotten dressed - she just had to touch up her lip gloss. Kim put
on a blouse, and nothing else, but escorted us to the door. We made a
date to meet again tomorrow for lunch at the restaurant. Kim said she
would also invite Tiffany from the condo rental office.
Patti & I left and returned to our condo. It was late, so we both got
undressed, removed our makeup, put on nighties and went to bed.
We woke the next morning and showered, I had to shave, and do our make-up
and get dressed for the day. I put on another cute dress and Patti was
again excited at how totally feminine I looked. It was a little later
this morning, so we went back into town to one of the many restaurants
for brunch. After eating, we again wandered around, window-shopping and
checking out the sights. It was now after noon and Patti said it was time
to go back over to Kim's house. When we arrived Kim opened the front door
wearing a skimpy 2-piece swim suit and ushered us in. Randy was already
there wearing his swim trunks. No question what was happening this
afternoon! I smiled at Randy and asked what was his pleasure! Kim laughed
and said I was adapting to my new life quite quickly! Patti smiled and
agreed with Kim.
Kim ushered all of us out to the pool area. She rifled thru and found a
couple 2-piece suits for Patti and me. We went into the bath house and
changed - though I guess we could have stripped in front of Randy & Kim!
We went back to the pool and Randy asked Patti if she would be interested
in letting him pleasure her orally. She didn't hesitate, pulled off her
swim suit bottom, and lay back on one of the recliner chairs. Randy threw
a towel down for his knees and dove into Patti like a starving dog. She
was squealing in no time! While Randy was eating Patti, I turned to Kim
and she dropped her swim suit bottom and lay back as well. I followed
Randy's example with a towel to cushion my knees and buried my face in
Kim's crotch. Both Patti and Kim were exhausted about the same time, so
Randy and I sat back up and let them recover. I went over to Randy and
asked if he was ready for me. He went over to another recliner, lay back
and let me give him a slow blow job. When he exploded into my mouth, I
did everything I could to swallow his entire load. Patti and Kim were
both beside us giving encouragement and telling me what a good job I was
doing.
I finished and went over to the outside bar for a drink. Turning to
Randy, I asked if he was ready for round two. He said he needed a minute,
and Kim took him into her mouth to help him recover. When he was hard
again, she pulled out a condom and put it on Randy, then stood and told
me to take over. I dropped my swim suit bottom, letting my penis flop
around, and proceeded to mount Randy. Once he entered me, I came almost
immediately, and he pumped and emptied his load into me.
We all then slipped into the pool to refresh and cool off. Once we got
out, we all dropped our remaining swim suit parts and toweled dry. Patti
and I went back to the bath house and got dressed. Kim and Randy were
exploring each other, so we got drinks and sat down to watch the show.
Big question on who was pleasuring who the most! This was an episode for
a porn channel!
When Kim and Randy finally exhausted each other, they wrapped up in
towels and joined Patti and me for a drink. It was now mid-afternoon, and
Kim suggested we should go into town for dinner. Patti and I were already
dressed, so we left and went to get a table.
We went back to the restaurant and told Laurie that Kim and Randy would
be joining us shortly. She seated us in a booth and Leslie came over to
see what we wished to order. We told here we were waiting on Kim and
Randy, but ordered glasses of wine to sip until they arrived. Ashley, the
bartender, came over and asked how we were enjoying our time in town.
Patti procedded to give her all the details of how I had been pleasuring
Randy! With a big grin, Ashley asked if we would be interested in
spending an evening with her. I was shocked, but Patti immediately said
that was an execellent idea. Patti asked Ashley what was her drink of
choice and she described a wonderful martini. Ashley said she would be
getting off work in an hour - about the time we would be finishing
dinner. Patti told Ashley which condo complex we were in and our unit
number. She said she would come over as soon as she got off work.
Kim and Randy walked in and came to the table looking very flushed - they
had been fucking again! We all ordered dinner and another round of
drinks. Patti told Kim that we were going to spend after-dinner with
Ashley. Kim smiled at me and said she was sure it would be and enjoyable
evening, and winked! When dinner was done, we thanked Kim and Randy for a
very wonderful afternoon and left.
Returning to the condo, Patti and I both needed to change and refresh our
makeup. I made a shaker of martinis and chilled 3 glasses in the freezer.
Patti came out at the same time the door bell rang and ushered Ashley in.
I retrieved the glasses and poured each a martini. We toasted to new
friends and enjoyable company.
Ashley asked how I was enjoying myself with Randy. I acknowledged the new
experiences and feelings. She sat back and began to tell us of her
transformation from a high-school football jock to a gorgeous female. I
was in shock! To look at her, you would never believe she was not a
genetic girl! The hair, the smile, the eyes, the boobs - everything you
would ever look for in a girl. She continued to explain her life and then
stood up and dropped her shorts and panties, exposing her penis. What the
hell - I moved over and took her in my mouth and proceeded to give her a
blow-job! It didn't take long, and she exploded into my mouth - I was
able to take her load without dripping any! Patti congratulated me and we
all toasted new found experiences! Ashley commented that she wasn't often
the recipient of a blow-job, she was normally giving them! I asked her if
she would like to fuck me, and she immediately said yes. Patti moved over
and started sucking on Ashley to get her hard again. Once Ashley was
hard, Patti pulled out a condom and stroked it onto her penis. I pulled
my panties down and bent over the back of the sofa. Ashley penetrated me
and stroked several times before coming again. She backed away, grabbed
some tissue and removed the condom, throwing it in the trash. We both
pulled our panties back up, sat down and enjoyed our martini.
A little while later, Ashley decided it was time to go, gave Patti and me
big kisses, and left.
Patti and I decided it was time for bed, so we went into the bath and
removed our makeup and changed into nighties. Once in bed, I asked if she
would like me to pleasure her orally. She pulled her panties off and put
her legs up into the air! I dove down and proceded to pleasure her until
she finally pushed me away. She asked if I needed satisfaction and I
declined, saying that the entire weekend had been exquisite. We drifted
off to sleep.
We woke the next morning and showered, I had to shave, and do our make-up
and get dressed for the day. It was time for us to pack up and check out.
I put on another cute dress and Patti was again excited at how totally
feminine I looked. We stopped at the condo complex office to check out.
Tanja and Tiffany were not to be denied a detailed description of our
weekend. Patti told them of our meeting with Kim, my liasion with Randy -
multiple times! She also told of our evening with Ashley. Both girls were
giddy about everything and hoped we would return sometime soon!
It was a little later in the morning, so we went back into town to one of
the many restaurants for brunch. Kim and Randy were at the restaurant,
obviously having spent the evening together. We joined them and chatted
about the weekend and Kim asked if we might want to return some time
soon. Patti immediately said we would be back as soon as our schedules
would allow.
Since I was so into pleasuring her orally, she said she intended to keep
me enfemme as much as possible. Kim agreed with that reasoning, and said
she enjoyed when I satisfied her orally as well.
Patti and I left and returned home, but there were now major changes in
our relationship. Without causing any humiliation, she encouraged me to
dress enfemme as much as possible. Our sex life also changed, I was to
always satisfy her orally, to which I didn't object in any way!
I certainly enjoy that she now encourages my crossdressing. We plan to
return and visit Kim in the very near future.
Kierra
- 03.01.2021
- 15
- 0
