Rileys first DP experience
- 2 years ago
- 12
- 0
Riley's Summer - Part 2 free porn video
I was awakened by Deb. She came into the room with a breakfast tray.
"Good morning, girls! You should eat breakfast and get out in the sun.
It's such a nice day." She picked up some dirty laundry from the floor,
and left us. "So how was it sleeping in a nightie?" Jamie asked. I
smiled, yawned and answered: "It was very nice, actually."
"Perhaps I should get me one of these myself?" I joked. Jamie didn't seem
to get the joke, and replied: "It's yours." Before I could object, Jamie
suggested that we could go to the beach. "Sure," I said. Jamie got out of
bed, and stretched. "Listen , Riley, I have a suggestion. Let's dress up
as girls for a week. You can sleep here, and your aunt won't see you." He
was right about that. Aunt Ann was completely absorbed in gardening, and
didn't go much out much. "I'm not sure, Jamie. It's very good fun to
dress up and all that, but a whole week?" Jamie tilted his head, and
said: "Come on! Can't you do it for me?" I did enjoy dressing up, and
this was way more exciting than spend my summer reading books. "Okay. Why
not," I said. "That's my boy," Jamie said and grinned, "or rather, that's
my girl." We went over to his dresser, and I picked a white bra, and a
white thong. Jamie also picked white underwear, although his panty was a
boy short. Jamie handed me a strapless green beach dress. I grabbed
everything together with a clean gaff, and headed to the bathroom. On my
way over there I met Frank, Jamie's father. He was as genial as the day
before, and didn't comment on me wearing a nightie. It was becoming
almost natural to cross dress, but just almost.
Jamie helped me to apply some make-up, and to glue some fake breasts on
my chest. They weren't big, rather quite small - but, they were firm and
very lifelike. When Jamie was finished it really looked like I had
breasts. "You can even swim in them," he said. I decided to not wear a
bra, as I was going to wear a strapless dress. "Find some bikinis or
swimsuits in the dresser, and I'll just get in the shower," Jamie said as
he headed for the bathroom. Jamie had at least 10 bikinis, and a couple
of swimsuits. I held a swimsuit in front of me. It was a one-piece
competition swimsuit. It looked really tight fitting, and I decided I
would bring that along. I found a golden bikini with a triangle top and
side-tie bottom. Jamie also glued some fake breasts on his chest, and I
had to help him. We walked out of the cottage and down the road to the
beach. To my delight, we didn't meet anyone.
The beach was as desolate as it always was, and we changed into our
bikinis. Jamie looked absolutely ravishing in his yellow push-up bikini.
He, or perhaps rather she, was already quite tan. I applied sun lotion on
her back, and massaged it into her skin. When I reached her bum, I
hesitated, but I continued. After all, Jamie had his hands on my cock
yesterday. Her bikini bottom was quite skimpy, and I was turned on again.
Jamie told me to lie down. It was my turn, and Jamie's hands felt overly
good on my back, butt on legs. We talked a lot, and the subject of
conversation turned back into sex again. It was my choice, but I couldn't
help it. The wind on my hairless legs and sensual feeling of wearing a
thong under a summer dress, together with the massage and lying on the
beach in a skimpy bikini was almost too much for me. "Do you have a
boyfriend," I asked. "Yes," Jamie said, as if he expected a sleazy
proposal. "Tell me about him, please," I asked. "His name is John, and
he's five years older than me. He's attending university, and he is very
handsome and manly. He has a great muscular body, and a fantastic cock,"
Jamie giggled. I don't know why I smiled, and why I felt slightly
jealous. "So you like macho men, then?" Jamie, rolled over and looked at
me. "Yeah, I do. You're very pretty and all that, but you aren't my type.
Neither as a boy, nor as a girl. As a partner, I mean. I like them fit
and strong. And besides I only like to be on the receiving end," she said
coyly. "Oh, I see," I said. Why was I feeling disappointed? It wasn't
because she told me I was an feminine boy. I knew that already.
We decided to go swimming, and I changed into the swimsuit. How much
better was it to wear swimsuits, than speedos! It was tight, and you
could see the curves of the breasts and nipples. I was almost mad with
the desire to jerk off, but how could I? I was spending every minute with
Jamie. The water was much warmer today, so we spent some time swimming.
When we reached the shore I noticed a man walking along the beach. My
heart rate accelerated. The man held a fishing rod in his hand. He
stopped when he reached us. I desperately wanted to hide or run away.
Jamie did most of the talking. He was a local, and I noticed he was
checking out our bodies. Would he notice? I don't think he did, because
when he left I turned my head to see, he was checking out my butt. He
gave me wink. I blushed and turned around. "See," Jamie said
triumphantly, "I told you that your ass is gorgeous. Now he's thinking of
fucking your brains out." I blushed even more. But a thought started to
form in my brain.
My aunt was happy to let me stay at Jamie's, and she even talked to her
parents. A couple of days later Jamie came into her room. She was very
happy about something. "John's coming!" she said. "He's coming over
today. My parents are going to France for the weekend, and we have the
place to ourselves." I was disappointed, as I knew the cross-dressing
days were over. At least for the weekend. "Oh, okay," I said, "I guess
I'll get back to my aunt." Jamie made a silly face, and said: "Duh! Don't
be silly, you are going to stay here. It's going to be fun. We can drink
and have a party. Oh, and he's bringing a friend!" I thought that a party
would be great, and I hadn't had a beer in long time. Auntie was strict
about that, and why should I drink alone anyway? I smiled, but then it
hit me. A friend? "Well, in that case I'll change into my normal boy's
clothes," I said. "We have an agreement, Riley. One week in girls
clothes. You promised me." I looked blankly at her, as I couldn't figure
out what to say. I was growing accustomed to wearing dresses and bikinis
in front of Jamie and her parents, and even the odd passerby. "Let's go
to the beach and get ourselves tan," Jamie said and grabbed my hand. I
already wore a bikini under my dress, so I followed her out into the
sunshine.
As we lay on the beach I wondered how the weekend would be. How John's
friend would be like. On how I was going to react if he was hitting on
me, and if I were going to have sex with him. I thought of myself giving
head to this guy. The thought both distressed and turned me on. Jamie
disturbed my thinking when she straddled me to apply sun lotion on my
back. The warmth of her hands on my back, and the feeling of her buttocks
resting gently on mine, only interrupted when she stretched to get more
lotion, made me tingle. I hadn't masturbated for five days, which was a
new record for me by a long shot. My dick was almost constantly trying to
get erect, but the gaff made it impossible. It was starting to be very
uncomfortable. I needed to cum, either by hand or by fucking Jamie's
tight and round ass. I looked at Jamie as she lay on the side with her
back to me. Her black bikini made her look so sexy, and the bikini bottom
had moved slightly into her crack. I shook my head, and opened my book.
What was I thinking? She was a he, and I was sure as hell was straight.
Was her ability to look so very much like a girl confusing me? Or was I
gay, or bisexual or something? Jamie commented on my silence when we
walked back. I apologized and told her that I was a little tired.
Frank and Deb was just leaving as we walked up the driveway. "Have a nice
time, girls," Deb cooed as the BMW rolled towards the gate. We waved them
goodbye, and Jamie took her arm around my shoulder. "Look, why don't you
go and have a shower? I'm sure you will feel better then," Jamie said. I
nodded, and walked upstairs. I found a cream and pink bustier, a matching
thong and nude colored stockings. I had tried the dress on before, and I
liked it a lot. It was short, but so was all of Jamie's dresses, and it
was tight fitting. I really enjoyed wearing body hugging clothing. I
brought this with, and went into the bathroom. I undressed in front of
the mirror. I noticed I had gotten a really nice tan. I was shocked when
I saw the tan lines from the bikini. I turned around and saw lines on my
back. Oh god, it was totally noticeable. I swore, and got into the
shower. I thought about jerking off, but I didn't. It felt wrong to do
that in someone else's shower, and in any case I wasn't in the mood. I
looked down on my breasts. I didn't feel comfortable about dressing up
anymore. I wanted to go back to Aunt Ann, and just have a normal boring
summer. Jamie was right though, the shower made me feel better. I felt
fresh and clean as I stepped out. My wet hairless legs looked very
feminine. Jamie had given me complements about them before, as well as my
butt. I had longer legs than her, and a slightly bigger bum. I felt sexy
as I stepped into the thong. I smiled as I looked in the mirror at the
thong vanishing between my cheeks as I pulled them up. I struggled a bit
with the bustier, it was more tricky than a bra. I was already doing a
decent makeup. Jamie was a good teacher. I felt very beautiful as I
looked at myself in the mirror.
"Wow, Riley! You look stunning. You better look out for John's friend.
He'll go bonkers when he sees you in that!" Riley said enthusiastically.
"Thanks," I smiled. I was feeling very feminine in my "new" body, and I
loved wearing stockings. I chose a purple and black sequin dress, as it
was very classy and body hugging. "Mom has lent me their bedroom for the
weekend," Jamie said as she removed her bikini top. I mumbled an okay,
while I straightened the dress. "So you and John's buddy will sleep
here," Jamie said casually.
My jaw dropped. "Excuse me?" I gasped. Jamie stood naked in the middle of
the room. She had also distinct tan lines. "What did you think? John and
I haven't seen each other for a month, and I'm barely keeping myself from
asking you to have sex with me." That last bit of information made me
pause, but I said: "I don't think that's such a good idea. What if he,
well, becomes frisky?" Riley smiled one of her Mona Lisa smiles. "It's
only two bedrooms here, so you really need to share this one with him. I
see you are getting used to be your feminine Riley," she giggled. I
blushed. It was true, I was concerned to share a bed with a man, although
I had done just that for the last four days. "Don't worry, Riley. You
don't need to have sex with him, and if you do, you won't get pregnant."
We both laughed at this. I felt much more relaxed now.
Riley had changed into a really sexy and really short body hugging black
dress. She looked spectacular. We had opened a bottle of white wine, and
we were both a little giggly, when the boys arrived. I had decided to
play it cool, and not worry about the outcome. Whatever happens, happens.
Right? John was tall, blonde and well-built. He was obviously happy to
see Jamie, and they kissed passionately on the front porch. I was
slightly embarrassed by this, but I politely shook John's friend. He was
slightly lower than John, and not as husky. He was by no means a wimp, as
his muscles showed through his shirt. "I'm Tom. Nice to meet you," he
said and smiled warmly, "you look really pretty." I blushed and thanked
him. I went to get them a glass of wine, and I noticed Tom looking at me
the whole time. I sat next to Tom on the sofa. He was on the diving team
at John's university, and studies economics. They had met at the student
union, where John was president. I felt a little shy, not only for being
younger, but also because the way Tom treated me. He was a real
gentleman, and he made me feel like a woman.
A few hours later we were all pretty liquored up, and I was much more at
ease. I let Tom fetch me drinks, and he listened intently the few times I
spoke. I told him how Jamie and I met, and how Jamie had convinced me to
be feminized. He told me that he never had seen a girl who looked so
beautiful as me. I was flattered; after all I had done a lot to get ready
for this evening. John and Jamie had a hard time not to shred their
clothes of. Soon after they said good night, and left for bed. The
thought of what would happen in the bedroom aroused me. I kept thinking
of John fucking Jamie hard in the ass. Oh, how I would have loved to be a
fly on the wall! Tom went over to the stereo, and put some soft rock.
"Cheers," I said and lifted my glass. Tom returned the gesture, and sat
down next to me. Tom talked about how he met Jamie once at Uni, and then
he stealthily put his arm around my shoulders.
I noticed that he turned to face me. He placed his hands around my face
and kissed. It was a really nice kiss. I opened my mouth and let his
tongue find mine. Tom slowly turned me against him and gently lowered me
on my back. Tom smiled, and lowered himself on top of me. This was a
strange new feeling for me. The feeling of a man over me. The weight of
him. The feeling of not being able to move. At first I felt trapped and
helpless, but Tom's kissing drove the slight feeling of panic away. I
relaxed. I loved his kisses and caresses. I felt I meant something for
him, and that he enjoyed this. Tom lay over me, for what seemed like an
eternity. We were joined together in a long passionate kiss. I noticed
that Tom's right hand stroked my leg, and I relished the feeling of his
hand against my smooth nylon stockings. Tom ended the kiss and rose, but
bent down over me. He moved one hand under my shoulders, and another
under my legs and lifted me effortlessly of the sofa. When he stood
upright I put my hands around his neck and lifted my head against his. We
were again joined together in a passionate kiss.
Tom gently broke off the kiss, and carried me gently and silently through
the living room, up the stairs and into the bedroom. He slowly lowered
unto the bed, and sat down beside me. With one hand behind my back he
unzipped my dress and unhurriedly pulled it over my head. He stopped and
declared: "Wow, you're beautiful. More beautiful than I could have
imagined." I was lying on the bed only wearing the bustier, thong,
stockings and a pair of pumps. Tom rose slowly, and reached out a hand. I
grabbed it and he pulled me next to him. He whispered: "Undress me.
Slowly." I unbuttoned his shirt button for button. His chest was muscular
and he had a six pack. Not an ounce of fat. I was impressed. I stepped
closer and felt his naked chest against mine. His shirt fell silently on
the floor, and I gripped his belt buckle and opened it and unzipped his
jeans. I bowed down and grabbed his trousers, and slowly pulled them
down. Tom stepped out of them when they reached his ankles. I was now
facing his groin, and I could clearly see that he wasn't unaffected by
the situation. I put my hand on his briefs, feeling the cock. At the same
time I felt Tom's hands on my neck. He pushed me lightly towards his
member. Soon I could place a soft kiss on the fabric feeling the swelling
of his member underneath.
I was intensly aroused. I knew well what Tom wanted me to do, but could
I? In what seemed like a long time, I sat silently on my knees in front
of Tom, with just the fabric between my mouth and his cock. I lifted my
hands, and grabbed the elastics. I looked up at Tom, and he looked so
hot. I pulled the briefs down, and suddenly his dick swung out. I jumped
back a little, and looked at his erect cock in front of me. I mustered
all my courage and wrapped my fingers around it. It was warm, hard and
stiff. It was absolutely nothing disgusting about it. I slowly lent
forward, and lightly kissed it. Tom grabbed me under my arms and lifted
me up so we were standing face to face. "Come," Tom said and laid me down
on the bed along him. We kissed deeply, and our tongues played with each
other. Tom turned, so that I was again facing his cock. He pulled down my
thong and then my gaff. I have to admit I was also affected, as my much
smaller cock had been erect for a while. Tom wrapped his fingers around
it and masturbated me slowly. Oh, how I longed for this!
I grabbed Tom's cock and returned his touches. I directed the hard cock
towards my mouth and kissed the head, and then I stuck out my tongue and
licked it. Slowly I opened my mouth, and let my lips embrace it. A little
more of it entered my mouth as I moved my head closer to his groin. I
started to suck it, and I soon felt an incredible delightful warmth
around my own as Tom started to suck mine. My arousal absorbed me. I felt
like a real woman, being together with a man. I did indeed look like a
woman, I had breasts, wore lingerie, stockings and pumps. I was a woman,
and now I was pleasing a man. Sucking his magnificent cock, and felt it
becoming even more erect in my mouth. The shyness was completely gone,
and I felt carried away in the love making. Feeling the pleasures Tom did
to me, feeling his hands on my body, feeling his hands on my buttocks,
feeling his fingers playing with my anus, my pussy. His touches was
amazing, and I felt a wave of pleasure. I cupped his testicles, and
sucked his cock.
I felt something cool and moist being smeared on my pussy. I enjoyed it
when he entered me with a finger, soon followed by two. I enjoyed the
feeling when his fingers excited me. I let his cock slide out of my
mouth, and said: "Oh, Tom, please continue. It's so amazing. I love the
feeling of your fingers. And your cock... It's so wonderful!" I took his
cock in my mouth again and sucked. I noticed that the desire grabbed Tom.
He started to move his hips, so that his cock slid in an out of my mouth.
Tom had three fingers inside me, and the repeated motion of them relaxed
my sphincter. Tom withdrew, and turned facing me. He laid down between my
legs and felt my breasts. I felt his cock against my butt. The touch sent
shocks through my body. I gasped. I caressed Tom's neck, and lifted my
legs and placed them around his waist. Tom sat up, and lifted my lower
body up slightly. I felt his cock against my pussy. Slowly I felt it
entering me. Tom leant forward, and placed a hand on my left breast, and
steadied himself on the bed with the other. The he leant forward and
kissed me.
I was really turned on now. I felt his rigid cock in my bum, and enjoyed
his kisses. He started to fuck me slowly. Pushed his cock inside me. Kept
it there a moment, and let it slide out, and then in again. Tom tried to
straighten up, but I locked my lips to his as I didn't want to break off
the kiss. I finally let him go. He cupped my buttocks, and as he pulled
me a little up, his cock penetrated me deeper than before. I gasped. I
lifted my legs up towards my head, to give Tom better access. He rewarded
me with a kiss. He moved his cock faster in and out of my ass. The
feeling was amazing. I noticed Tom's excitement. Now I was a proper
woman. A woman, who no longer was a virgin. A woman who was being fucked
thoroughly by a hot, sexy man. A man I felt obliged to indulge. I
whimpered of pleasure. Enjoyed the feeling of Tom's cock working like a
piston in my virgin pussy. It penetrated deeply, and then out and in
again. Suddenly Tom thrust his cock into me as deep as could. His cock
had grown even more, as he fucked me. He trusted a few times more, and
then I felt his sperm erupt inside me. He trusted some more, and even
more sperm gushed out. Slowly Tom slouched over me, but he kept his cock
inside.
I was fatigued, and I felt his now shrinking cock still sheathed in my
pussy. We lay there a long time. We enjoyed the fatigue and the feeling
of pleasure still in our bodies. Tom withdrew his cock, stood up, but
bent down to kiss me. "You sexy little thing. You are so damn hot!" Tom
said and walked out to the bathroom. Shortly after he came back, and laid
down beside me. We started kissing again, and exploring each other's
body. Tom turned around and started to tease my dick. I wrapped my
fingers around his cock. It was nice and clean. I slowly masturbated him,
licked the top, let in slide in my mouth and felt it grew erect. I
enjoyed the feeling of my own dick in Tom's mouth. I felt the ecstasy
running wild. I sucked the best I could, and suddenly Tom's came. Spurted
loads of sperm into my mouth. The experience was so strong that I came. I
shuddered as the orgasm overwhelmed me. When the orgasm subsided, Tom
turned over and lay over me, and said: "Open your mouth." Obediently I
did, and received my own cum. I circled my tongue and let Tom's mix with
my own sperm. I enjoyed the salty and sweet taste of it, before I
swallowed it. Tom lay lazily down beside me, and said: "You're fantastic.
Simply fantastic." I smiled to him. Tom smiled back. I felt drowsy, but
senses it when Tom covered me with the sheet. Before I fell asleep I felt
Tom's muscular body against mine and his arm as he put it around me.
Madison
- 10.09.2020
- 13
- 0
Summering in Femininity Part 1 A Bummer Summer
- 2 years ago
- 35
- 0
Her Story to Summer a tale about Summer s daddy
- 2 years ago
- 28
- 0
