Surprise package

My daughter often brings her roommate home with her when she visits.

The story being, that her roommate and her parents don’t have a good relationship.

We always have an open attitude, and welcoming to all.

 On this visit, our daughter asked if it was alright for her roommate to stay for the summer break. She didn’t really have anywhere to go, since we had extra bedrooms we said it would be fine.

  After a few weeks, I noticed that her roommate always wore a sundress. Never seen her in shorts, jeans, or bathing suit.

They had been home for about a month, my daughter was going to a cabin for the weekend with friends. 

She asked if it was ok for her roommate to stay home, she wasn’t comfortable going with her.

I said sure, that your mom isn’t going to be home, and I have yard work to do. 

So nothing exciting was going on.

Late Saturday after spending the day doing yard work, I took a shower.

Then made a drink and chilled out on the deck.

I went inside to make another drink and my daughter’s roommate came from her room.

I asked if she would like a drink and join me on the deck.

She did join me, during our conversations she seemed hesitant with her answers.

I went in a made us a couple more drinks, she seemed to relax more and talked more freely.

During our conversations, she mentioned her relationship with her parents was bad because of some decisions she made.

I said, I can’t imagine what a child could do that the parent would disown them.

She said you might be surprised.

As the night went on, we continued drinking and talking.

I started to notice how beautiful, smooth her legs look. I tried not to focus on her full lips either as we talked, but found it difficult.

 Wasn’t sure if it was my imagination or not, but it seemed as if she noticed me checking her out. It seemed she was teasing me, let her dress move up showing more of her leg.

When she came back from going to the bathroom, she sat next to me.

Her legs were crossed, and seem to press up against mine.

While talking her body language seem flirtatious, and she often touched my arm, shoulder.

At some point, my hand moved to her leg just above her knee.

Unconsciously started caressing her leg, slowly moving up her thigh.

I noticed she seemed to loose track of our conversation, that when I noticed my hand on her leg.

I quickly moved my hand, and apologized. She said that an apology wasn’t necessary.

That it felt nice, that it had been a long time since anyone has hugged or touched her.

She reached over taking my hand and placed it back in her leg.

I immediately felt my cock get hard.

I was also a little nervous, her was a girl my daughters age, her roommate.

I was thinking this wasn’t a good idea, but I was very attracted to her.

She placed her hand on my thigh, and started slowly caressing my leg.

Our conversation grew quiet, as we both seemed preoccupied with our desires.

Her fingers brushed against my hard cock, tracing the length, then teasing the tip of my cock through my shorts.

See looks at me, I reach over pulling her close. Our lips meet, our tongues exploring each other’s mouths.

Then she starts sucking on my tongue, I moan with pleasure, my cock is throbbing.

She squeezes my cock, stroking it as she sucks on my tongue.

I break our kiss, I can’t take it anymore, taking her by the hand, I say let’s go inside.

Once inside the house, she turns, wrapping her arms around my neck.

We kiss, my hands on her hips, slide up, I feel her erect nipples.

My hands push her sundress off her shoulders.

I kiss her neck, then her shoulder, then take her firm breast in my hand.

I teased her nipple with my tongue, then started sucking on her breast.while she kept rubbing my cock through my pants.

She then unzipped my pants, reached in a grabbed my cock. I almost came as I felt her soft hand wrap around my cock, slowly sliding up and down the shaft.

She then knelt in front of me, teasing the tip of my cock with her tongue.

Then I felt her full soft lips press around my cock. 

She took me deep into her mouth, I ran my fingers through her hair.

Her pace quickened, my hips started rocking in rhythm.

I got lost in how great it felt, I held her head as I thrust my cock as deep as I could.

My legs grew weak as I climax, I held her head as I filled her mouth.

Then I took her hand and lead her to the bedroom.

 She seemed hesitant to enter, I asked if something was wrong?

She said I think I should share something with you before.

She said, the reason my family and I aren’t getting along, is because I use to be a male.

I said what do you mean you use to be a male.

She said three years ago I started hormones therapy, and started identifying as a female, rather than a male.

I said so do you mean, you are a transgender woman ?

She said yes, I will admit, first reaction I was stunned. I didn’t know what to say.

Then I remembered how turned on I was not long ago.

I remembered how I had fantasized about being with a transgender woman, but knew she needed to be feminine.

Here I was with a transgender woman, she was feminine, I never would have guessed otherwise.

I told her, I would like to still spend time with you. I still want you, I am just not sure how far I can go. If she is alright with knowing I might not be able to do something’s, but I do want to try.

We kissed, her arms around my neck, I slid her sundress over her hips, letting it fall to the floor.

I reached down and slid her panties off, then saw her erection.

That’s why I always seen her wearing a dress, so you couldn’t see a bulge.

We kissed, she reached down and started stroking my cock, my hand slowly moved down.

I felt her erection, I started stroking her.

I was surprised, I found myself getting very turned on.

Her breathing started getting faster, moans escaped her lips between kisses.

I decided I wanted to try and give her, the pleasure she gave me earlier.

I knelt down in front of her, took her cock, teasing the tip with my tongue.

Then I took her cock in my mouth.

I heard her moaning, I felt her hand caress my head.

Then she started thrusting her cock deeper into my mouth. She held my head as she pushed her cock deep inside.

I was surprised at how turned on I was getting.

Her moans became louder, then I felt her explode in my mouth, I couldn’t swallow it though.

She started crying, I asked what was wrong?

She said nothing, it just felt so good, she had never really had sex before.

I responded, really, your a virgin?

She said more or less, before hormone therapy, I had tried to have sex with a girl.

But it didn’t go well, I was so confused with my feelings.

I said, I am surprised, because it sure seemed like you knew what you were doing when you gave me a blowjob.

She said I think it was because I felt a connection with you, I wanted to please you.

I had to ask, so you have never had sex like a transgender woman would, from behind?

She said no, I have never done anything, never been involved with anyone that way.

She said, but I will try that with you, if you want to.

I trust you, but you would need to go slow, and use some form of lubricant.

My cock again got hard, the thought of being the first person to have her that way.

But then reality hit, I didn’t deserve to take that from her.

We layed on the bed, cuddling, talking, touching each other.

We were jerking each other off, then she said let’s change positions, she turned away from me, and layed on her side.

I cuddled up next to her, kissing her neck, and shoulders.

My hands caressing her soft skin, then her hips.

I noticed that she was rocking her hips, which caused my hard cock to slide up and down the crack of her butt cheeks.

I started rocking my hips, my cock sliding along her butt, turned me on.

I held her hips, grinding against her, I heard her moan, our breathing became more rapid.

She reach over to the nightstand, grabbed the lubricant I left sitting there.

Put some in her hand, then began stroking my cock.

My cock easily slid up and down her butt crack.

Teasing myself when it found her butt hole.

I push against her, then it would slip by, I continued doing this, my cock getting harder and harder.

Passionate building between us, she reached between her legs, grabbed my cock, a held it against her butt hole.

She than pressed back against me, I felt the head of my cock push inside her.

She let out a gasp, her breathing was very rapid.

It was hard not to ram my cock inside her, I wanted to be inside her.

She continued holding my cock, allowing a little more than the head to go inside her.

I held on to her hips, thrusting my hips.

I knew I was close to coming, I wanted her to come to, I reached around and wrapped my hand around her hard cock.

I stroked her In rhythm with my thrust.

I said I am going to come, I can’t hold off any longer.

As I exploded inside her butt, I felt her cock twitch, and she came to.

We layed in silence, neither sure what to say.

Then I held her hand, and asked would you like to do hat to me ?

She said maybe next time, I think we have gone a long way already tonight.